Filed Pursuant to Rule 424(b)(3)
Registration No. 333-173404

Dear Berkshire Hills Bancorp Stockholder:

On December 21, 2010, Berkshire Hills Bancorp, Inc. entered into a merger agreement to acquire Legacy Bancorp, Inc. in a stock and cash transaction. If the merger agreement is approved and the merger is subsequently completed, Legacy Bancorp, Inc. will merge into Berkshire Hills Bancorp.

The shares of Legacy Bancorp, Inc. common stock owned by each Legacy Bancorp, Inc. stockholder will be converted into the right to receive 0.56385 shares of Berkshire Hills Bancorp, Inc. common stock and $1.30 in cash. If Berkshire Hills and Legacy must divest deposit liabilities in order to comply with a requirement contained in any regulatory approval, and if the weighted average deposit premium that Berkshire Hills receives for those divested deposits exceeds 350 basis points, then Berkshire Hills will be required under the Merger Agreement to make an additional cash payment to Legacy stockholders that, in the aggregate, will equal 50% of the premium in excess of 350 basis points (net of applicable taxes on such excess premium). Such payment would occur following completion of any such divestiture which is anticipated to occur after completion of the Merger.

The maximum number of shares of Berkshire Hills Bancorp, Inc. common stock estimated to be issuable upon completion of the merger is 6,203,000.

As a result of the merger, Legacy Bancorp, Inc. stockholders will become stockholders of Berkshire Hills Bancorp, Inc.

Your board of directors has unanimously determined that the merger and the merger agreement are fair and in the best interests of Berkshire Hills Bancorp, Inc. and its stockholders and unanimously recommends that you vote “FOR” adoption of the merger agreement. The merger cannot be completed unless a majority of the outstanding shares of common stock of Berkshire Hills Bancorp, Inc. vote to adopt the merger agreement. Whether or not you plan to attend the special meeting of stockholders, please take the time to vote by completing the enclosed proxy card and mailing it in the enclosed envelope. If you sign, date and mail your proxy card without indicating how you want to vote, your proxy will be counted as a vote “FOR” adoption of the merger agreement. If you fail to vote, or you do not instruct your broker how to vote any shares held for you in “street name,” it will have the same effect as voting “AGAINST” the merger agreement.

In addition, Berkshire Hills stockholders will consider an amendment to our Certificate of Incorporation to increase the number of shares of common stock we are authorized to issue from 26 million shares to 50 million shares. This proposal is separate and distinct from, and not conditioned upon, the outcome of the stockholder vote for the proposed merger with Legacy Bancorp, Inc.

The accompanying document is also being delivered to Legacy Bancorp, Inc. stockholders as Berkshire Hills Bancorp, Inc.’s prospectus for its offering of Berkshire Hills Bancorp, Inc. common stock in connection with the merger, and as a proxy statement for the solicitation of proxies from Legacy Bancorp, Inc. stockholders to vote for the adoption of the merger agreement and approval of the merger.

This Joint Proxy Statement/Prospectus provides you with detailed information about the proposed merger. It also contains or references information about Berkshire Hills Bancorp, Inc. and Legacy Bancorp, Inc. and related matters. You are encouraged to read this document carefully. In particular, you should read the “Risk Factors” section beginning on page 7 for a discussion of the risks you should consider in evaluating the proposed merger and how it will affect you.

Voting procedures are described in this Joint Proxy Statement/Prospectus. Your vote is important, so I urge you to cast it promptly. Berkshire Hills Bancorp, Inc.’s management enthusiastically supports the acquisition of Legacy Bancorp, Inc., and joins with our board of directors in recommending that you vote “FOR” adoption of the merger agreement. We also recommend that you vote “FOR” the amendment of our Certificate of Incorporation.

Sincerely,

Michael P. Daly
President and Chief Executive Officer

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Dear Legacy Bancorp Stockholder:

On December 21, 2010, Berkshire Hills Bancorp, Inc. entered into a merger agreement to acquire Legacy Bancorp, Inc. in a stock and cash transaction. If the merger agreement is approved and the merger is subsequently completed, Legacy Bancorp, Inc. will merge into Berkshire Hills Bancorp, Inc.

Each share of Legacy Bancorp, Inc. common stock owned by each Legacy Bancorp, Inc. stockholder will be converted into the right to receive 0.56385 shares of Berkshire Hills Bancorp, Inc. common stock and $1.30 in cash. If Berkshire Hills and Legacy must divest deposit liabilities in order to comply with a requirement contained in any regulatory approval, and if the weighted average deposit premium that Berkshire Hills receives for those divested deposits exceeds 350 basis points, then Berkshire Hills will be required under the Merger Agreement to make an additional cash payment to Legacy stockholders that, in the aggregate, will equal 50% of the premium in excess of 350 basis points (net of applicable taxes on such excess premium). Such payment would occur following completion of any such divestiture which is anticipated to occur after completion of the merger.

The maximum number of shares of Berkshire Hills Bancorp, Inc. common stock estimated to be issuable upon completion of the merger is 6,203,000.

As a result of the merger, Legacy Bancorp, Inc. stockholders will become stockholders of Berkshire Hills Bancorp, Inc.

Your board of directors has unanimously determined that the merger and the merger agreement are fair and in the best interests of Legacy Bancorp, Inc. and its stockholders and unanimously recommends that you vote “FOR” adoption of the merger agreement. The merger cannot be completed unless a majority of the issued and outstanding shares of common stock of Legacy Bancorp, Inc. entitled to be cast vote to adopt the merger agreement. Whether or not you plan to attend the special meeting of stockholders, please take the time to vote by completing the enclosed proxy card and mailing it in the enclosed envelope. If you sign, date and mail your proxy card without indicating how you want to vote, your proxy will be counted as a vote “FOR” adoption of the merger agreement. If you fail to vote, or you do not instruct your broker how to vote any shares held for you in “street name,” it will have the same effect as voting “AGAINST” the merger agreement.

The accompanying document is being delivered to Legacy Bancorp, Inc. stockholders as Berkshire Hills Bancorp, Inc.’s prospectus for its offering of Berkshire Hills Bancorp, Inc. common stock in connection with the merger, and as a proxy statement for the solicitation of proxies from Legacy Bancorp, Inc. stockholders to vote for the adoption of the merger agreement and approval of the merger.

Legacy Bancorp, Inc. stockholders have dissenters’ rights and may receive payment in cash of the fair value of their shares, excluding any appreciation in value that results from the merger. To maintain dissenters’ rights, a stockholder must (1) deliver written notice of its intent to demand payment for its shares to Legacy Bancorp, Inc. before the special meeting of Legacy stockholders or at the special meeting but before the vote is taken and (2) either vote against the merger or not submit a proxy. See “Questions and Answers About the Merger and the Special Meetings” on page ii and “Rights of Dissenting Legacy Bancorp, Inc. Stockholders” on page 34. A copy of the section of the Delaware General Corporation Law pertaining to dissenters’ rights is included as Appendix D to the accompanying Joint Proxy Statement/Prospectus.

This Joint Proxy Statement/Prospectus provides you with detailed information about the proposed merger. It also contains or references information about Berkshire Hills Bancorp, Inc. and Legacy Bancorp, Inc. and related matters. You are encouraged to read this document carefully. In particular, you should read the “Risk Factors” section beginning on page 7 for a discussion of the risks you should consider in evaluating the proposed merger and how it will affect you.

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Voting procedures are described in this Joint Proxy Statement/Prospectus. Your vote is important, so I urge you to cast it promptly. Legacy Bancorp, Inc.’s management enthusiastically supports the merger with Berkshire Hills Bancorp, Inc., and joins with our board of directors in recommending that you vote “FOR” adoption of the merger agreement.

		Sincerely,
		J. Williar Dunlaevy Chief Executive Officer and Chairman of the Board

Joint Proxy Statement/Prospectus dated May 6, 2011
and first mailed to stockholders on or about May 13, 2011

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WHERE YOU CAN FIND MORE INFORMATION

Both Berkshire Hills Bancorp, Inc. and Legacy Bancorp, Inc. file annual, quarterly and special reports, proxy statements and other business and financial information with the Securities and Exchange Commission (the “SEC”). You may read and copy any materials that either Berkshire Hills Bancorp, Inc. or Legacy Bancorp, Inc. files with the SEC at the SEC’s Public Reference Room at 100 F Street, N.E., Room 1580, Washington, D.C. 20549, at prescribed rates. Please call the SEC at (800) SEC-0330 ((800) 732-0330) for further information on the public reference room. In addition, Berkshire Hills Bancorp, Inc. and Legacy Bancorp, Inc. file reports and other business and financial information with the SEC electronically, and the SEC maintains a website located at http://www.sec.gov containing this information. You will also be able to obtain these documents, free of charge, from Berkshire Hills Bancorp, Inc. at www.berkshirebank.com under the “Investor Relations” link and then under the heading “SEC filings” or from Legacy Bancorp, Inc. by accessing Legacy Bancorp, Inc.’s website at www.legacybanks.com under the “Investors” link and then under the heading “SEC Filings.”

Berkshire Hills Bancorp, Inc. has filed a registration statement on Form S-4 to register with the SEC up to 6,203,000 shares of Berkshire Hills Bancorp, Inc. common stock. This Joint Proxy Statement/Prospectus is a part of that registration statement. As permitted by SEC rules, this Joint Proxy Statement/Prospectus does not contain all of the information included in the registration statement or in the exhibits or schedules to the registration statement. You may read and copy the registration statement, including any amendments, schedules and exhibits at the addresses set forth below. Statements contained in this document as to the contents of any contract or other documents referred to in this Joint Proxy Statement/Prospectus are not necessarily complete. In each case, you should refer to the copy of the applicable contract or other document filed as an exhibit to the registration statement. This Joint Proxy Statement/Prospectus incorporates by reference documents that Berkshire Hills Bancorp, Inc. and Legacy Bancorp, Inc. have previously filed with the SEC. They contain important information about the companies and their financial condition. See “Where You Can Find More Information” on page 96. These documents are available without charge to you upon written or oral request to the applicable company’s principal executive offices. The respective addresses and telephone numbers of such principal executive offices are listed below:

Berkshire Hills Bancorp, Inc. 24 North Street Pittsfield, Massachusetts 01201 Attention: Investor Relations Department (413) 236-3239		Legacy Bancorp, Inc. 99 North Street Pittsfield, Massachusetts 01201 Attention: Investor Relations (413) 445-3513

To obtain timely delivery of these documents, you must request the information no later than June 13, 2011 in order to receive them before Berkshire Hills Bancorp, Inc.’s special meeting of stockholders or Legacy Bancorp, Inc.’s special meeting of stockholders.

Berkshire Hills Bancorp, Inc. common stock is traded on the NASDAQ Global Select Market under the symbol “BHLB,” and Legacy Bancorp, Inc. common stock is traded on the NASDAQ Global Market under the symbol “LEGC.”

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BERKSHIRE HILLS BANCORP, INC.
  
24 NORTH STREET
PITTSFIELD, MASSACHUSETTS 02101
  
NOTICE OF THE SPECIAL MEETING OF STOCKHOLDERS
TO BE HELD ON JUNE 20, 2011

NOTICE IS HEREBY GIVEN that a special meeting of the stockholders of Berkshire Hills Bancorp, Inc. will be held at The Crowne Plaza Hotel, One West Street, Pittsfield, Massachusetts, at 11:00 a.m., Eastern Standard Time, on June 20, 2011, for the following purposes:

1. To consider and vote upon a proposal to adopt the Agreement and Plan of Merger, dated as of December 21, 2010, by and between Berkshire Hills Bancorp, Inc. and Legacy Bancorp, Inc., and thereby to approve the transactions contemplated by the merger agreement, including the merger of Legacy Bancorp, Inc. with and into Berkshire Hills Bancorp, Inc.;

2. The amendment of our Certificate of Incorporation to increase the number of shares of common stock we are authorized to issue from 26 million to 50 million;

3. To approve one or more adjournments of the special meeting, if necessary or appropriate, including adjournments to permit further solicitation of proxies in favor of the merger; and

4. To transact any other business which may properly come before the special meeting or any adjournment or postponement thereof.

The proposed merger is described in more detail in this Joint Proxy Statement/Prospectus, which you should read carefully in its entirety before you vote. A copy of the merger agreement is attached as Appendix A to this Joint Proxy Statement/Prospectus. Only Berkshire Hills Bancorp, Inc. stockholders of record as of the close of business on May 2, 2011, are entitled to notice of and to vote at the special meeting of stockholders or any adjournments of the special meeting.

To ensure your representation at the special meeting of stockholders, please follow the voting procedures described in the accompanying Joint Proxy Statement/Prospectus and on the enclosed proxy card. This will not prevent you from voting in person, but it will help to secure a quorum and avoid added solicitation costs. Your proxy may be revoked at any time before it is voted.

BERKSHIRE HILLS BANCORP, INC.’S BOARD OF DIRECTORS UNANIMOUSLY RECOMMENDS THAT YOU VOTE “FOR” ADOPTION OF THE MERGER AGREEMENT, “FOR” THE AMENDMENT TO OUR CERTIFICATE OF INCORPORATION, AND “FOR” THE ADJOURNMENT PROPOSAL DESCRIBED ABOVE.

BY ORDER OF THE BOARD OF DIRECTORS

Wm. Gordon Prescott
Corporate Secretary and General Counsel

Pittsfield, Massachusetts
May 13, 2011

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YOUR VOTE IS IMPORTANT!

WHETHER OR NOT YOU EXPECT TO ATTEND THE BERKSHIRE HILLS BANCORP SPECIAL MEETING IN PERSON, BERKSHIRE HILLS BANCORP URGES YOU TO SUBMIT YOUR PROXY AS PROMPTLY AS POSSIBLE BY COMPLETING, SIGNING AND RETURNING THE PROXY CARD OR VOTING INSTRUCTION CARD AND RETURNING IT IN THE POSTAGE-PAID ENVELOPE PROVIDED. If your shares are held in the name of a bank, broker or other nominee, please follow the instructions on the voting instruction card furnished to you by such record holder.

If you have any questions concerning the merger or other matters to be considered at the Berkshire Hills Bancorp, Inc. special meeting, would like additional copies of this Joint Proxy Statement/Prospectus or need help voting your shares, please contact Berkshire Hills Bancorp, Inc.’s proxy solicitor:

Phoenix Advisory Partners, LLC
110 Wall Street, 27^th Floor
New York, New York 10005
1-800-576-4314 (toll free)
1-212-493-3910 (call collect)

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LEGACY BANCORP, INC.
  
99 NORTH STREET
PITTSFIELD, MASSACHUSETTS 01201
  
NOTICE OF THE SPECIAL MEETING OF STOCKHOLDERS
TO BE HELD ON JUNE 20, 2011

NOTICE IS HEREBY GIVEN that a special meeting of the stockholders of Legacy Bancorp, Inc. will be held at The Crowne Plaza Hotel, One West Street, Pittsfield, Massachusetts at 9:30 a.m., Eastern Standard Time, on June 20, 2011, for the following purposes:

1. To consider and vote upon a proposal to adopt the Agreement and Plan of Merger, dated as of December 21, 2010, by and between Berkshire Hills Bancorp, Inc. and Legacy Bancorp, Inc., and thereby to approve the transactions contemplated by the merger agreement, including the merger of Legacy Bancorp, Inc. with and into Berkshire Hills Bancorp, Inc.;

2. To approve one or more adjournments of the special meeting, if necessary or appropriate, including adjournments to permit further solicitation of proxies in favor of the merger; and

3. To transact any other business which may properly come before the special meeting or any adjournment or postponement thereof.

The proposed merger is described in more detail in this Joint Proxy Statement/Prospectus, which you should read carefully in its entirety before voting. A copy of the merger agreement is attached as Appendix A to this Joint Proxy Statement/Prospectus. Only Legacy Bancorp, Inc. stockholders of record as of the close of business on May 2, 2011, are entitled to notice of and to vote at the special meeting of stockholders or any adjournments of the special meeting.

To ensure your representation at the special meeting of stockholders, please follow the voting procedures described in the accompanying Joint Proxy Statement/Prospectus and on the enclosed proxy card. This will not prevent you from voting in person, but it will help to secure a quorum and avoid added solicitation costs. Your proxy may be revoked at any time before it is voted.

BY ORDER OF THE BOARD OF DIRECTORS

Kimberly A. Mathews
Corporate Secretary and General Counsel

Pittsfield, Massachusetts
May 13, 2011

LEGACY BANCORP, INC.’S BOARD OF DIRECTORS UNANIMOUSLY RECOMMENDS THAT YOU VOTE “FOR” ADOPTION OF THE MERGER AGREEMENT AND “FOR” THE ADJOURNMENT PROPOSAL DESCRIBED ABOVE.

DO NOT SEND STOCK CERTIFICATES WITH THE PROXY CARD. YOU WILL RECEIVE A LETTER OF TRANSMITTAL WITH INSTRUCTIONS FOR DELIVERING YOUR STOCK CERTIFICATES UNDER SEPARATE COVER.

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YOUR VOTE IS IMPORTANT!

WHETHER OR NOT YOU EXPECT TO ATTEND THE LEGACY BANCORP, INC. SPECIAL MEETING IN PERSON, LEGACY BANCORP, INC. URGES YOU TO SUBMIT YOUR PROXY AS PROMPTLY AS POSSIBLE BY COMPLETING, SIGNING AND DATING THE ENCLOSED PROXY CARD AND RETURNING IT IN THE POSTAGE-PAID ENVELOPE PROVIDED. If your shares are held in the name of a bank, broker or other nominee, please follow the instructions on the voting instruction card furnished to you by such record holder.

If you have any questions concerning the merger or other matters to be considered at the Legacy Bancorp, Inc. special meeting, would like additional copies of this Joint Proxy Statement/Prospectus or need help voting your shares, please contact Legacy Bancorp, Inc.’s proxy solicitor:

Phoenix Advisory Partners, LLC
110 Wall Street, 27^th Floor
New York, New York 10005
1-800-576-4314 (toll free)
1-212-493-3910 (call collect)

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		Page
QUESTIONS AND ANSWERS ABOUT THE MERGER AND THE SPECIAL MEETINGS			ii
SUMMARY			1
RISK FACTORS			7
CAUTION ABOUT FORWARD-LOOKING STATEMENTS			11
SELECTED HISTORICAL FINANCIAL INFORMATION			12
SELECTED HISTORICAL FINANCIAL AND OTHER DATA OF BERKSHIRE HILLS BANCORP, INC.			13
SELECTED HISTORICAL FINANCIAL AND OTHER DATA OF LEGACY BANCORP, INC.			15
UNAUDITED PRO FORMA COMBINED CONDENSED CONSOLIDATED FINANCIAL INFORMATION RELATING TO THE ROME AND LEGACY MERGERS			17
MARKET PRICE AND DIVIDEND INFORMATION			29
SPECIAL MEETING OF LEGACY BANCORP, INC. STOCKHOLDERS			30
SPECIAL MEETING OF BERKSHIRE HILLS BANCORP, INC. STOCKHOLDERS			32
RIGHTS OF DISSENTING LEGACY BANCORP, INC. STOCKHOLDERS			34
DESCRIPTION OF THE MERGER			38
DESCRIPTION OF BERKSHIRE HILLS BANCORP, INC. CAPITAL STOCK			87
COMPARISON OF RIGHTS OF STOCKHOLDERS			89
MANAGEMENT AND OPERATIONS AFTER THE MERGER			92
BERKSHIRE HILLS PROPOSAL II — AMENDMENT OF THE BERKSHIRE HILLS BANCORP, INC. CERTIFICATE OF INCORPORATION TO INCREASE THE NUMBER OF AUTHORIZED SHARES OF COMMON STOCK			93
ADJOURNMENT OF THE SPECIAL MEETINGS			94
LEGAL MATTERS			94
EXPERTS			94
STOCKHOLDER PROPOSALS			95
WHERE YOU CAN FIND MORE INFORMATION			96
BERKSHIRE HILLS BANCORP, INC. FILINGS (FILE NO. 000-51584)			97
LEGACY BANCORP, INC. FILINGS (FILE NO. 000-51525)			98
Appendix A Agreement and Plan of Merger			A-1
Appendix B Fairness Opinion of Keefe Bruyette & Woods, Inc.			B-1
Appendix C Fairness Opinion of Sandler O’Neill & Partners, L.P.			C-1
Appendix D Section 262 of the Delaware General Corporation Law (Dissenters’ rights)			D-1
Appendix E Text of Proposed Amendment to Berkshire Hills Bancorp, Inc. Certificate of Incorporation			E-1

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QUESTIONS AND ANSWERS ABOUT THE MERGER AND THE SPECIAL MEETINGS

The following are answers to certain questions that you may have regarding the merger and the special meetings. We urge you to read carefully the remainder of this Joint Proxy Statement/Prospectus because the information in this section may not provide all the information that might be important to you in determining how to vote. Additional important information is also contained in the appendices to, and the documents incorporated by reference in, this Joint Proxy Statement/Prospectus.

If Berkshire Hills and Legacy must divest deposit liabilities in order to comply with a requirement contained in any regulatory approval, and if the weighted average deposit premium that Berkshire Hills receives for those divested deposits exceeds 350 basis points, then Berkshire Hills will be required under the Merger Agreement to make an additional cash payment to Legacy stockholders that, in the aggregate, will equal 50% of the premium in excess of 350 basis points (net of applicable taxes on such excess premium). Such payment would occur following completion of any such divestiture which is anticipated to occur after completion of the Merger.

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Under Delaware law, the Merger cannot be completed unless Berkshire Hills stockholders vote to adopt the Merger Agreement and approve the Merger. By this Joint Proxy Statement/Prospectus, Berkshire Hills’s board of directors is soliciting proxies of Berkshire Hills stockholders to provide this approval at the special meeting of Berkshire Hills stockholders discussed below.

Under Delaware law, the Merger cannot be completed unless Legacy stockholders vote to adopt the Merger Agreement and approve the Merger. By this Joint Proxy Statement/Prospectus, Legacy’s board of directors is soliciting proxies of Legacy stockholders to provide this approval at the special meeting of Legacy stockholders discussed below.

For a more detailed discussion of the material United States federal income tax consequences of the transaction, including the tax consequences of the aggregate divestiture premium (described on pages 68 and 70) that may be paid to Legacy stockholders as additional cash consideration for such stockholders’ shares of Legacy common stock, please see the section “Description of the Merger — Material Tax Consequences of the Merger” beginning on page 68.

The consequences of the Merger to any particular stockholder will depend on that stockholder’s particular facts and circumstances. Accordingly, you are urged to consult your tax advisor to determine your tax consequences from the Merger.

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Under the Delaware General Corporation Law, record holders of Legacy common stock who do not vote in favor of the proposal to adopt the Merger Agreement and who deliver a notice of intent to demand payment will be entitled to seek appraisal rights in connection with the Merger, and if the Merger is completed, obtain payment in cash equal to the fair value of their shares of Legacy common stock as determined by the Court of Chancery of the State of Delaware, instead of the Merger consideration. To exercise their appraisal rights, Legacy stockholders must strictly follow the procedures prescribed by Delaware law. These procedures are summarized in this Joint Proxy Statement/Prospectus. In addition, the text of the applicable provisions of Delaware law is included as Appendix D to this document. Failure to strictly comply with these provisions will result in the loss of appraisal rights. For a more complete description of appraisal rights, please refer to the section entitled “Appraisal Rights” beginning on page D-1.

Legacy stockholders also are being asked to approve one or more adjournments of the special meeting, if necessary or appropriate, including adjournments to permit further solicitation of proxies in favor of the Legacy Merger Agreement proposal, which we refer to as the “Legacy adjournment proposal.”

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Legacy’s board of directors also unanimously recommends that Legacy stockholders vote “FOR” the Legacy adjournment proposal.

Approval of the Legacy adjournment proposal will require the affirmative vote of a majority of the voting power of the shares of Legacy common stock present in person or represented by proxy at the special meeting and entitled to vote on the Legacy adjournment proposal. Abstentions will have the same effect as shares voted against the Legacy adjournment proposal, and broker non-votes will not affect whether the Legacy adjournment proposal is approved.

As of the record date for the special meeting, directors and executive officers of Legacy, together with their affiliates, had sole or shared voting power over approximately 4.2% of the Legacy common stock outstanding and entitled to vote at the special meeting.

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If you have instructed a broker to vote your shares, you must follow your broker’s directions to change your vote.

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Berkshire Hills stockholders also are being asked to approve an amendment to Berkshire Hills Bancorp, Inc. Certificate of Incorporation to increase the number of shares of common stock we are authorized to issue from 26 million to 50 million and to approve one or more adjournments of the special meeting, if necessary or appropriate, including adjournments to permit further solicitation of proxies in favor of the Berkshire Hills Bancorp Merger Agreement proposal or the amendment to the Berkshire Hills Bancorp, Inc. Certificate of Incorporation, which we refer to as the “Berkshire Hills Bancorp adjournment proposal.”

Berkshire Hills Bancorp’s board of directors also unanimously recommends that Berkshire Hills stockholders vote “FOR” the amendment to the Berkshire Hills Bancorp, Inc. Certificate of Incorporation and “FOR” the Berkshire Hills Bancorp adjournment proposal.

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As of the record date for the special meeting, directors and executive officers of Berkshire Hills, together with their affiliates, had sole or shared voting power over approximately 3.1% of the Berkshire Hills common stock outstanding and entitled to vote at the special meeting.

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If you have instructed a broker to vote your shares, you must follow your broker’s directions to change your vote.

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SUMMARY

This summary highlights selected information in this Joint Proxy Statement/Prospectus and may not contain all of the information important to you. To understand the Merger more fully, you should read this entire document carefully, including the documents attached to this Joint Proxy Statement/Prospectus.

The Companies

Berkshire Hills Bancorp, Inc.
24 North Street
Pittsfield, Massachusetts 01201
(413) 443-5601

Berkshire Hills, a Delaware corporation, is a savings and loan holding company headquartered in Pittsfield, Massachusetts that was incorporated and commenced operations in 2000. Berkshire Hills’ common stock is listed on The NASDAQ Global Select Market under the symbol “BHLB.” Berkshire Hills conducts its operations primarily through Berkshire Bank, a Massachusetts chartered savings bank with 48 full-service branch offices in western Massachusetts, northeastern and central New York and southern Vermont. Berkshire Bank’s experienced banking team offers comprehensive deposit, lending and wealth management products to personal and business accounts. Berkshire Hills is also the holding company for Berkshire Insurance Group, a full service Massachusetts insurance agency providing both personal and business insurance services. At December 31, 2010, Berkshire Hills had total assets of $2.9 billion, total deposits of $2.2 billion and total stockholders’ equity of $388 million.

On April 1, 2011, Berkshire Hills completed its acquisition of Rome Bancorp, Inc. (“Rome”) and The Rome Savings Bank. The aggregate merger consideration paid to the Rome stockholders was approximately 2,597,000 shares of Berkshire Hills common stock and approximately $22.1 million cash. At December 31, 2010, Rome had total assets of $327.2 million, total deposits of $225.3 million, total stockholders’ equity of $60.7 million provided through five full-service community banking offices in Rome, Lee and New Hartford, New York, all of which opened as branches of Berkshire Bank on April 1, 2011.

Legacy Bancorp, Inc.
99 North Street
Pittsfield, Massachusetts 01201
(413) 443-4421

Legacy, a Delaware corporation, is a one-bank holding company headquartered in Pittsfield, Massachusetts that was incorporated and commenced operations in 2005. Legacy’s common stock is quoted on the NASDAQ Global Market under the symbol “LEGC.” Legacy conducts its operations primarily through Legacy Banks, a Massachusetts-chartered stock savings bank offering products and services to individuals, families and business through 19 branch offices in western Massachusetts and eastern New York State. Predecessors to Legacy Banks have been serving the area’s financial needs since 1835. Legacy Banks’ business consists primarily of making loans to its customers, including residential mortgages, commercial real estate loans, commercial loans and consumer loans, and investing in a variety of investment and mortgage-backed securities. Legacy Banks funds these lending and investment activities with deposits from the general public, funds generated from operations and select borrowings. Legacy Banks also provides insurance and investment products and services, investment portfolio management, debit and credit card products and online banking. Its primary business includes residential and commercial real estate lending, small business loan and deposit services as well as variety of consumer loan and deposit services. At December 31, 2010, Legacy had total assets of $916.9 million, total deposits of $685.2 million and total stockholders’ equity of $111.6 million.

Special Meeting of Legacy Bancorp, Inc. Stockholders; Required Vote (page 30)

A special meeting of Legacy stockholders is scheduled to be held at The Crowne Plaza Hotel, One West Street, Pittsfield, Massachusetts at 9:30 a.m., local time, on June 20, 2011. At the special meeting, you will be asked to vote on a proposal to approve the Merger Agreement between Legacy and Berkshire Hills. You may also be asked to vote to adjourn the special meeting, if necessary, to permit further solicitation of proxies if there are not sufficient votes at the time of the meeting to approve the Merger Agreement.

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Only Legacy stockholders of record as of the close of business on May 2, 2011 are entitled to notice of, and to vote at, the Legacy special meeting and any adjournments or postponements of the meeting.

Approval of the Merger Agreement requires the affirmative vote of holders of a majority of the outstanding shares of Legacy common stock entitled to vote. As of the record date, there were 8,631,732 shares of Legacy common stock outstanding and entitled to vote. The directors and executive officers of Legacy, as a group, beneficially owned 360,386 shares of Legacy common stock, representing approximately 4.2% of the outstanding shares of Legacy common stock as of the record date and have agreed to vote their shares in favor of the Merger at the special meeting.

Special Meeting of Berkshire Hills Bancorp, Inc. Stockholders; Required Vote (page 32)

A special meeting of Berkshire Hills stockholders is scheduled to be held at The Crowne Plaza Hotel, One West Street, Pittsfield, Massachusetts at 11:00 a.m., local time, on June 20, 2011. At the special meeting, you will be asked to vote on a proposal to approve the Merger Agreement between Legacy and Berkshire Hills, and an amendment to the Berkshire Hills Certificate of Incorporation to increase the number of authorized shares of common stock from 26 million to 50 million. You may also be asked to vote to adjourn the special meeting, if necessary, to permit further solicitation of proxies if there are not sufficient votes at the time of the meeting to approve the Merger Agreement or the amendment to the Berkshire Hills Certificate of Incorporation.

Only Berkshire Hills stockholders of record as of the close of business on May 2, 2011 are entitled to notice of, and to vote at, the Berkshire Hills special meeting and any adjournments or postponements of the meeting.

Approval of the Merger Agreement requires the affirmative vote of holders of a majority of the outstanding shares of Berkshire Hills common stock entitled to vote. Under the Berkshire Hills Certificate of Incorporation and Bylaws and Delaware law, the amendment of Berkshire Hills Certificate of Incorporation requires a vote “FOR” the amendment by a majority of the outstanding Common Stock entitled to vote thereof. As of the record date, there were 16,779,110 shares of Berkshire Hills common stock outstanding. The directors and executive officers of Berkshire Hills, as a group, beneficially owned 521,087 shares of Berkshire Hills common stock, representing approximately 3.1% of the outstanding shares of Berkshire Hills common stock as of the record date.

The Merger and the Merger Agreement (page 38)

Berkshire Hills’ acquisition of Legacy is governed by the Merger Agreement. The Merger Agreement provides that, if all of the conditions are satisfied or waived, Legacy will be merged with and into Berkshire Hills with Berkshire Hills as the surviving entity. We encourage you to read the Merger Agreement, which is included as Appendix A to this Joint Proxy Statement/Prospectus.

What Legacy Bancorp, Inc. Stockholders Will Receive in the Merger (page 66)

Under the Merger Agreement, each share of Legacy common stock will be exchanged for 0.56385 shares of Berkshire Hills common stock and $1.30 in cash. If Berkshire Hills and Legacy must divest deposit liabilities in order to comply with a requirement contained in any regulatory approval, and if the weighted average deposit premium that Berkshire Hills receives for those divested deposits exceeds 350 basis points, then Berkshire Hills will be required under the Merger Agreement to make an additional cash payment to Legacy stockholders that, in the aggregate, will equal 50% of the premium in excess of 350 basis points (net of applicable taxes on such excess premium). Such payment would occur following completion of any such divestiture, which is anticipated to occur after completion of the Merger.

Comparative Market Prices (page 66)

The following table shows the closing price per share of Berkshire Hills common stock and the equivalent price per share of Legacy common stock, giving effect to the Merger, on December 21, 2010, which is the last day on which shares of Berkshire Hills common stock traded preceding the public announcement of the proposed Merger, and on May 2, 2011, the most recent practicable date prior to the mailing of this Joint Proxy Statement/Prospectus. The equivalent price per share of Legacy common stock was

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computed by multiplying the price of a share of Berkshire Hills common stock by the 0.56385 exchange ratio. The equivalent price per share of Legacy common stock does not include the $1.30 cash portion of the Merger Consideration. See “Description of the Merger — Consideration to be Received in the Merger” on page 66.

		Berkshire Hills Bancorp, Inc. Common Stock				Equivalent Price Per Share of Legacy Bancorp, Inc. Common Stock
December 21, 2010		$	21.28			$	12.00
May 2, 2011		$	21.51			$	12.13

Recommendation of Legacy Bancorp, Inc. Board of Directors (page 47)

The Legacy board of directors has unanimously approved the Merger Agreement and the proposed merger. The Legacy board believes that the Merger Agreement, including the Merger contemplated by the Merger Agreement, is fair to, and in the best interests of, Legacy and its stockholders, and therefore unanimously recommends that Legacy stockholders vote “FOR” the proposal to approve the Merger Agreement. In its reaching this decision, Legacy’s board of directors considered a variety of factors, which are described in the section captioned “Description of the Merger — Recommendation of the Legacy Board of Directors; Legacy’s Reasons for the Merger” beginning on page 47.

The Legacy board of directors unanimously recommends that Legacy stockholders vote “FOR” the proposal to adjourn the special meeting to a later date or dates, if necessary, to permit further solicitation of proxies if there are not sufficient votes at the time of the special meeting to approve the Merger Agreement.

Opinion of Legacy Bancorp, Inc.’s Financial Advisor (page 50)

In deciding to approve the Merger, one of the factors considered by Legacy’s board of directors was the opinion of KBW, which served as financial advisor to Legacy’s board of directors. KBW delivered its oral opinion on December 21, 2010, which was confirmed in writing on December 21, 2010, that the Merger consideration is fair to the holders of Legacy common stock from a financial point of view. The full text of this opinion is included as Appendix B to the Joint Proxy Statement/Prospectus. You should read the opinion carefully to understand the procedures followed, assumptions made, matters considered and limitations of the review conducted by KBW. Legacy has agreed to pay KBW a fee equal to 1.25 percent of the aggregate purchase price contingent upon completion of the Merger for its services in connection with the Merger. KBW has received a fee of $200,000 for the rendering of its fairness opinion, which fee shall be credited against the 1.25 percent fee referenced above if the Merger is completed.

Recommendation of Berkshire Hills Bancorp, Inc. Board of Directors (page 57)

The Berkshire Hills board of directors has unanimously approved the Merger Agreement and the proposed merger. The Berkshire Hills board believes that the Merger Agreement, including the Merger contemplated by the Merger Agreement, is fair to, and in the best interests of, Berkshire Hills and its stockholders, and therefore unanimously recommends that Berkshire Hills stockholders vote “FOR” the proposal to approve the Merger Agreement. In its reaching this decision, Berkshire Hill’s board of directors considered a variety of factors, which are described in the section captioned “Description of the Merger — Recommendation of Berkshire Hills Bancorp, Inc. Board of Directors and Reasons for Merger” beginning on page 57.

The Berkshire Hills board of directors has unanimously approved the amendment to the Certificate of Incorporation to increase the amount of authorized common stock from 26 million to 50 million. The Berkshire Hills board believes that the proposed amendment to the Certificate of Incorporation is in the best interests of Berkshire Hills and its stockholders, and therefore unanimously recommends that Berkshire Hills stockholders vote “FOR” the proposal to amend a Certificate of Incorporation.

The Berkshire Hills board of directors unanimously recommends that Berkshire Hills stockholders vote “FOR” the proposal to adjourn the special meeting to a later date or dates, if necessary, to permit further solicitation of proxies if there are not sufficient votes at the time of the special meeting to approve the Merger Agreement.

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Opinion of Berkshire Hills Bancorp, Inc.’s Financial Advisor (page 58)

In deciding to approve the Merger, one of the factors considered by Berkshire Hills’ board of directors was the opinion of Sandler O’Neill, which served as financial advisor to Berkshire Hills’ board of directors. Sandler O’Neill delivered its oral opinion on December 20, 2010, which was confirmed in writing on December 21, 2010, that the Merger consideration is fair to the holders of Berkshire Hills common stock from a financial point of view. The full text of this opinion is included as Appendix C to the Joint Proxy Statement/Prospectus. You should read the opinion carefully to understand the procedures followed, assumptions made, matters considered and limitations of the review conducted by Sandler O’Neill. Berkshire Hills has agreed to pay Sandler O’Neill a transaction fee of $810,000, of which $162,000 was paid upon the signing of the Merger Agreement and the remainder to be paid upon completion of the Merger. Sandler O’Neill also received a fee of $150,000 for the rendering of its fairness opinion.

Regulatory Matters Relating to the Merger (page 71)

Under the terms of the Merger Agreement, the Merger cannot be completed unless it is first approved by the Office of Thrift Supervision, the Massachusetts Division of Banks, the Massachusetts Board of Bank Incorporation and the Federal Deposit Insurance Corporation. Berkshire Hills has filed the required applications. As of the date of this document, Berkshire Hills has not received any approvals from those regulators. While Berkshire Hills does not know of any reason why it would not be able to obtain approval in a timely manner, Berkshire Hills cannot be certain when or if it will receive regulatory approval. As part of its regulatory filings, Berkshire Hills has requested the bank regulators and the United States Department of Justice to authorize Berkshire Hills and Legacy to divest approximately $162.0 million in deposits as well as four Legacy branch offices located in Berkshire County, Massachusetts. There can be no assurance as to whether the bank regulators or the United States Department of Justice will accept, deny or modify the proposed divestiture plan.

Conditions to Completing the Merger (page 79)

The completion of the Merger is subject to the fulfillment of a number of conditions, including:

Terminating the Merger Agreement (page 84)

The Merger Agreement may be terminated by mutual consent of Berkshire Hills and Legacy at any time prior to the completion of the Merger. Additionally, subject to conditions and circumstances described in the Merger Agreement, either Berkshire Hills or Legacy may terminate the Merger Agreement if, among other things, any of the following occur:

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Legacy also may terminate the Merger Agreement if Berkshire Hills’ stock price falls below thresholds set forth in the Merger Agreement and Berkshire Hills does not increase the exchange ratio pursuant to a prescribed formula.

Berkshire Hills may also terminate the Merger Agreement if Legacy materially breaches its agreements regarding the solicitation of other acquisition proposals and the submission of the Merger Agreement to stockholders or if the board of directors of Legacy does not recommend approval of the Merger in the Joint Proxy Statement/Prospectus or withdraws or revises its recommendation in a manner adverse to Berkshire Hills.

Termination Fee (page 86)

Under certain circumstances described in the Merger Agreement, Berkshire Hills may demand from Legacy Bancorp, Inc. a $4,320,000 termination fee in connection with the termination of the Merger Agreement. See “Description of the Merger — Termination Fee” on page 86 for a list of the circumstances under which a termination fee is payable.

Interests of Certain Persons in the Merger that are Different from Yours (page 73)

In considering the recommendation of the board of directors of Legacy to adopt the Merger Agreement, you should be aware that officers and directors of Legacy have employment and other compensation agreements or plans that give them interests in the Merger that are somewhat different from, or in addition to, their interests as Legacy stockholders. These interests and agreements, which provide for cash payments in the aggregate amount of approximately $9.3 million, include:

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Accounting Treatment of the Merger (page 68)

The Merger will be accounted for using the acquisition method in accordance with U.S. generally accepted accounting principles.

Comparison of Rights of Stockholders (page 89)

When the Merger is completed, Legacy stockholders who are to receive shares of Berkshire Hills will become Berkshire Hills stockholders and their rights will be governed by Delaware law and by Berkshire Hills’ certificate of incorporation and bylaws. See “Comparison of Rights of Stockholders” beginning on page 89 for a summary of the material differences between the respective rights of Legacy and Berkshire Hills stockholders.

Rights of Dissenting Stockholders (page 34)

Legacy stockholders have dissenters’ rights and may receive payment in cash of the fair value of their shares, excluding any appreciation in value that results from the merger. To maintain its dissenters’ rights a stockholder must (1) deliver written notice of its intent to demand payment for its shares to Legacy Bancorp, Inc. before the special meeting of Legacy stockholders or at the special meeting but before the vote is taken and (2) either vote against the merger or not submit a proxy. See “Rights of Dissenting Legacy Bancorp, Inc. Stockholders” on page 34.

Legacy stockholders may dissent from the Merger and, upon complying with the requirements of Delaware law, receive cash in the amount of the fair value of their shares instead of shares of Berkshire Hills common stock and/or the cash consideration specified in the Merger Agreement. A copy of the section of the Delaware General Corporation Law pertaining to dissenters’ rights is attached as Appendix D to this Joint Proxy Statement/Prospectus. You should read the statute carefully and consult with your legal counsel if you intend to exercise these rights.

Material Tax Consequences of the Merger (page 68)

Provided that the merger will qualify as a tax-free reorganization for United States federal income tax purposes, since Legacy stockholders will receive a combination of Berkshire Hills common stock and cash, Legacy stockholders may recognize gain, but not any loss, on the exchange of their stock for Berkshire Hills common stock and cash. For a more detailed discussion of the material United States federal income tax consequences of the transaction, including the tax consequences of the aggregate divestiture premium (described on pages 68 and 70) that may be paid to Legacy stockholders as additional cash consideration for such stockholders’ shares of Legacy common stock, please see the section “Description of the Merger — Material Tax Consequences of the Merger” beginning on page 68.

This tax treatment may not apply to all Legacy stockholders. Determining the actual tax consequences of the Merger to Legacy stockholders can be complicated. Legacy stockholders should consult their own tax advisor for a full understanding of the Merger’s tax consequences that are particular to each stockholder.

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RISK FACTORS

In addition to the other information contained in or incorporated by reference into this Joint Proxy Statement/Prospectus, you should consider carefully the risk factors described below, in deciding how to vote. You should keep these risk factors in mind when you read forward-looking statements in this document. Please refer to the section of this Joint Proxy Statement/Prospectus titled “Caution About Forward-Looking Statements” beginning on page 11.

The price of Berkshire Hills common stock will fluctuate, and therefore Legacy stockholders will not know until the effective time of the Merger the value of the consideration they will receive in the Merger.

Because the per share stock consideration is fixed at 0.56385 shares of Berkshire Hills common stock, the market value of the Berkshire Hills common stock to be issued in the Merger will depend upon the market price of Berkshire Hills common stock. This market price likely will vary from the closing price of Berkshire Hills common stock on the date the Merger was announced, on the date that this proxy statement/prospectus was mailed, and on the date of the Berkshire Hills or Legacy special meeting. Accordingly, at the time of the Legacy special meeting, Legacy stockholders will not necessarily know or be able to calculate the value of the stock consideration they would be entitled to receive upon completion of the Merger. You should obtain current market quotations for shares of Berkshire Hills common stock and for shares of Legacy common stock.

The price of Berkshire Hills common stock might decrease after the Merger.

Following the Merger, holders of Legacy common stock will become stockholders of Berkshire Hills. Berkshire Hills common stock could decline in value after the Merger. For example, during the twelve-month period ending on May 2, 2011 (the most recent practicable date before the printing of this Joint Proxy Statement/Prospectus), the closing price of Berkshire Hills common stock varied from a low of $16.93 to a high of $22.75 and ended that period at $21.51. The market value of Berkshire Hills common stock fluctuates based upon general market conditions, Berkshire Hills’ business and prospects and other factors. Further, the market price of Berkshire Hills common stock after the merger may be affected by factors different from those affecting the common stock of Berkshire Hills or Legacy currently. The businesses of Legacy and Berkshire Hills differ and, accordingly, the results of operations of the combined company and the market price of the combined company’s shares of common stock may be affected by factors different from those currently affecting the independent results of operations and market prices of common stock of each of Legacy and Berkshire Hills. For a discussion of the businesses of Legacy and Berkshire Hills and of certain factors to consider in connection with those businesses, see the documents incorporated by reference in this proxy statement/prospectus and referred to under “Where You Can Find More Information” beginning on page 96.

Berkshire Hills may be unsuccessful in pursuing a plan to divest certain deposits and other liabilities. Such proposed divestiture plan may constitute a material adverse effect on the parties.

Berkshire Hills and Legacy are both headquartered in Pittsfield, Massachusetts, and, as a result, each bank has a significant number of branches and deposit market share in and around their headquarters and the surrounding area. Berkshire Hills and Legacy have among the largest deposit market shares in the Pittsfield market area. As part of its regulatory filings, Berkshire Hills has requested the bank regulators and the United States Department of Justice to authorize Berkshire Hills and Legacy to divest approximately $162.0 million in deposits, as well as four Legacy branch offices located in Berkshire County, Massachusetts. There can be no assurance as to whether the bank regulators or the United States Department of Justice will accept, deny or modify the proposed divestiture plan, or the timing of such approvals.

In addition, any regulatory approval that includes a requirement that the parties divest more than $200.0 million of deposit liabilities, whether from Legacy, Berkshire Hills or a combination of the two, together with related branch premises and loans, may be considered a material adverse effect as defined in the Merger Agreement, and therefore be cause to terminate the Merger Agreement.

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There can be no assurance that any amount will be paid to Legacy stockholders in respect of divested deposit liabilities.

If Berkshire Hills and Legacy must divest deposit liabilities in order to comply with a requirement contained in any regulatory approval, and if the weighted average deposit premium that Berkshire Hills receives for those divested deposits exceeds 350 basis points, then Berkshire Hills will be required under the Merger Agreement to make an additional cash payment to Legacy stockholders that, in the aggregate, will equal 50% of the premium in excess of 350 basis points (net of applicable taxes on such excess premium). The right to such payment is not transferable. Such payment would occur following completion of any such divestiture, which is anticipated to occur after completion of the Merger. However, there can be no assurance that Berkshire Hills will be required to divest deposit liabilities. Additionally, in the event Berkshire Hills is required to do so, there can be no assurance that the weighted average deposit premium that Berkshire Hills receives for those divested deposits will exceed 350 basis points and the Legacy stockholders will receive any payment with respect to such divested deposit liabilities.

Berkshire Hills may be unable to successfully integrate Legacy’s operations and retain Legacy’s employees.

The Merger involves the integration of two companies that have previously operated independently. The difficulties of combining the operations of the two companies include:

The process of integrating operations could cause an interruption of, or loss of momentum in, the activities of the business and the loss of key personnel. The integration of the two companies will require the experience and expertise of certain key employees of Legacy who are expected to be retained by Berkshire Hills. Berkshire Hills may not be successful in retaining these employees for the time period necessary to successfully integrate Legacy’s operations with those of Berkshire Hills. The diversion of management’s attention and any delay or difficulty encountered in connection with the Merger and the integration of the two companies’ operations could have an adverse effect on the business and results of operation of Berkshire Hills following the Merger.

The termination fee and the restrictions on solicitation contained in the Merger Agreement may discourage other companies from trying to acquire Legacy

Until the completion of the Merger, with some exceptions, Legacy is prohibited from soliciting, initiating, encouraging or participating in any discussion of or otherwise considering any inquiry or proposal that may lead to an acquisition proposal, such as a merger or other business combination transaction, with any person other than Berkshire Hills. In addition, Legacy has agreed to pay a termination fee to Berkshire Hills in specified circumstances. These provisions could discourage other companies from trying to acquire Legacy even though those other companies might be willing to offer greater value to Legacy’s stockholders than Berkshire Hills has offered in the Merger. The payment of the termination fee could also have a material adverse effect on Legacy’s financial condition. Legacy was afforded the opportunity to solicit additional acquisition proposals from third parties from the date of the Merger Agreement until January 31, 2011, which resulted in no other offers being made to Legacy.

Certain of Legacy’s officers and directors have interests that are different from, or in addition to, interests of Legacy stockholders generally.

You should be aware that the directors and officers of Legacy have interests in the Merger that are different from, or in addition to, the interests of Legacy stockholders generally. These include: two current Legacy board members joining the Berkshire Hills board of directors upon completion of the Merger; severance payments that certain officers will receive under existing employment or change-in-control agreements, the offer of executive-level employment that the President of Legacy will become subject to upon completion of the Merger; a non-competition and consulting agreement entered into with the Chief Executive Officer of Legacy; the payment for stock options; and provisions in the Merger Agreement relating to

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indemnification of directors and officers and insurance for directors and officers of Legacy for events occurring before the Merger. For a more detailed discussion of these interests, see “Description of the Merger — Interests of Certain Persons in the Merger that are Different from Yours” beginning on page 73.

Failure to complete the Merger could negatively impact the stock prices and future businesses and financial results of Berkshire Hills and Legacy

If the Merger is not completed, the ongoing businesses of Berkshire Hills and Legacy may be adversely affected and Berkshire Hills and Legacy will be subject to several risks, including the following:

In addition, if the Merger is not completed, Berkshire Hills and/or Legacy may experience negative reactions from the financial markets and from their respective customers and employees. This risk may be particularly significant since the parties share the same primary market area. Berkshire Hills and/or Legacy also could be subject to litigation related to any failure to complete the Merger or to enforcement proceedings commenced against Berkshire Hills or Legacy to perform their respective obligations under the Merger Agreement. If the Merger is not completed, Berkshire Hills and Legacy cannot assure their stockholders that the risks described above will not materialize and will not materially affect the business, financial results and stock prices of Berkshire Hills and/or Legacy.

Legacy stockholders will have a reduced ownership and voting interest after the Merger and will exercise less influence over management of the combined organization.

Legacy stockholders currently have the right to vote in the election of the Legacy Board of Directors and on various other matters affecting Legacy. Upon the completion of the Merger, each Legacy stockholder will become a stockholder of Berkshire Hills with a percentage ownership of the combined organization that is much smaller than the stockholder’s percentage ownership of Legacy. It is expected that the former stockholders of Legacy as a group will receive shares in the merger constituting approximately 21.0% of the outstanding shares of Berkshire Hills common stock immediately after the Merger. As a result, Legacy stockholders will have significantly less influence on the management and policies of Berkshire Hills than they now have on the management and policies of Legacy.

The shares of Berkshire Hills common stock to be received by Legacy stockholders receiving the stock consideration as a result of the Merger will have different rights from shares of Legacy common stock.

Following completion of the Merger, Legacy stockholders who receive the stock consideration will no longer be stockholders of Legacy but will instead be stockholders of Berkshire Hills. Although Legacy and Berkshire Hills each are incorporated under Delaware law, there will be important differences between the current rights of Legacy stockholders and the rights of Berkshire Hills stockholders that may be important to Legacy stockholders. See “Comparison of Rights of Stockholders” beginning on page 89 for a discussion of the different rights associated with Berkshire Hills common stock and Legacy common stock.

The fairness opinion obtained by Legacy from its financial advisor does not reflect changes in circumstances subsequent to the date of the fairness opinion

KBW, Legacy’s financial advisor in connection with the Merger, has delivered to the board of directors of Legacy its opinion dated as of December 21, 2010. The opinion of KBW stated that as of such date, and based upon and subject to the factors and assumptions set forth therein, the Merger consideration to be paid to the holders of the outstanding shares of Legacy common stock pursuant to the Merger Agreement was fair

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from a financial point of view to such holders. The opinion does not reflect changes that may occur or may have occurred after the date of the opinion, including changes to the operations and prospects of Berkshire Hills or Legacy, changes in general market and economic conditions or regulatory or other factors. Any such changes, or changes in other factors on which the opinion is based, may materially alter or affect the relative values of Berkshire Hills and Legacy.

The fairness opinion obtained by Berkshire Hills from its financial advisor does not reflect changes in circumstances subsequent to the date of the fairness opinion

Sandler O’Neill, Berkshire Hills’s financial advisor in connection with the Merger, has delivered to the board of directors of Berkshire Hills its opinion dated as of December 21, 2010. The opinion of Sandler O’Neill stated that as of such date, and based upon and subject to the factors and assumptions set forth therein, the Merger consideration to be paid to the holders of the outstanding shares of Berkshire Hills common stock pursuant to the Merger Agreement was fair from a financial point of view to such holders. The opinion does not reflect changes that may occur or may have occurred after the date of the opinion, including changes to the operations and prospects of Legacy or Berkshire Hills, changes in general market and economic conditions or regulatory or other factors. Any such changes, or changes in other factors on which the opinion is based, may materially alter or affect the relative values of Legacy and Berkshire Hills.

There is no assurance when or even if the Merger will be completed.

Completion of the Merger is subject to satisfaction or waiver of a number of conditions. See “Description of the Merger — Conditions to Completing the Merger” on page 79. There can be no assurance that Berkshire Hills and Legacy will be able to satisfy the closing conditions or that closing conditions beyond their control will be satisfied or waived.

Berkshire Hills and Legacy can agree at any time to terminate the Merger Agreement, even if Legacy stockholders and Berkshire Hills stockholders have already voted to approve the merger agreement. Berkshire Hills and Legacy can also terminate the Merger Agreement under other specified circumstances.

The Merger is subject to the receipt of consents and approvals from regulatory authorities that may impose conditions that could have an adverse effect on Berkshire Hills or, if not obtained, could prevent completion of the Merger.

Before the Merger may be completed, various approvals and consents must be obtained from regulatory entities. These regulators may impose conditions on the completion of the Merger or require changes to the terms of the Merger. Any such conditions or changes could have the effect of delaying completion of the Merger or imposing additional costs on or limiting the revenues of Berkshire Hills following the Merger. In addition, pending elimination of the Office of Thrift Supervision and transfer of its responsibilities to other federal banking agencies may adversely affect the timely processing of the applications.

Either Berkshire Hills or Legacy may terminate the Merger Agreement if the Merger has not been completed by November 30, 2011, unless the failure of the merger to be completed has resulted from the failure of the party seeking to terminate the merger agreement to perform its obligations under the Merger Agreement.

Any failure to successfully integrate the businesses of Rome and Legacy or otherwise realize the expected benefits from Berkshire Hills’ recent mergers could adversely affect Berkshire Hills’ results of operations or financial condition.

There are significant risks and uncertainties associated with mergers and acquisitions. The success of Berkshire Hills’ mergers with Rome and Legacy will depend, in part, on Berkshire Hills’ ability to realize the anticipated benefits and cost savings from combining the businesses of Berkshire Hills with Rome and Legacy. If Berkshire Hills is are not able to successfully integrate these businesses, the anticipated benefits and cost savings of the acquisitions may not be realized fully or may take longer to realize than expected. For example, Berkshire Hills may fail to realize the growth opportunities and cost savings anticipated to be derived from the acquisition. In addition, as with regard to any of acquisition, a significant decline in asset valuations or cash flows may also cause Berkshire Hills not to realize expected benefits.

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To the extent that the purchase price, consisting of cash plus the number of shares of Berkshire Hills common stock issued or to be issued in the Rome and Legacy mergers, exceeds the fair value of the net assets, including identifiable intangibles of Rome and Legacy, at the respective merger dates, that amount will be reported as goodwill. In accordance with current accounting guidance, goodwill will not be amortized but will be evaluated for impairment annually. A failure to realize expected benefits of the Rome or Legacy merger could adversely impacting the carrying value of the goodwill recognized in those mergers, and in turn negatively affect Berkshire Hills’ financial condition.

CAUTION ABOUT FORWARD-LOOKING STATEMENTS

Certain statements contained in this document that are not historical facts may constitute forward-looking statements within the meaning of Section 27A of the Securities Act of 1933, as amended (referred to as the Securities Act), and Section 21E of the Securities Exchange Act of 1934, as amended (referred to as the Securities Exchange Act), and are intended to be covered by the safe harbor provisions of the Private Securities Litigation Reform Act of 1995. The sections of this document which contain forward-looking statements include, but are not limited to, “Questions And Answers About the Merger and the Special Meeting,” “ Summary,” “Risk Factors,” “Description of the Merger — Background of the Merger,” “Description of the Merger — Legacy’s 2011 Management Financial Projections,” and “Description of the Merger — Recommendation of the Legacy Board of Directors; Legacy’s Reasons for the Merger.” You can identify these statements from the use of the words “may,” “will,” “should,” “could,” “would,” “plan,” “potential,” “estimate,” “project,” “believe,” “intend,” “anticipate,” “expect,” “target” and similar expressions.

These forward-looking statements are subject to significant risks, assumptions and uncertainties, including among other things, changes in general economic and business conditions and the risks and other factors set forth in the “Risk Factors” section beginning on page 7.

Additional factors that could cause the results of Berkshire Hills or Legacy to differ materially from those described in the forward-looking statements can be found in the filings made by Berkshire Hills and Legacy with the Securities and Exchange Commission, including the Berkshire Hills Annual Report on Form 10-K for the fiscal year ended December 31, 2010 and the Legacy Annual Report on Form 10-K for the fiscal year ended December 31, 2010.

Because of these and other uncertainties, Berkshire Hills’ actual results, performance or achievements, or industry results, may be materially different from the results indicated by these forward-looking statements. In addition, Berkshire Hills’ and Legacy’s past results of operations do not necessarily indicate Berkshire Hills’ and Legacy’s combined future results. You should not place undue reliance on any of the forward-looking statements, which speak only as of the dates on which they were made. Neither Berkshire Hills nor Legacy is undertaking an obligation to update these forward-looking statements, even though its situation may change in the future, except as required under federal securities law. Each of Berkshire Hills and Legacy qualifies all of its forward-looking statements by these cautionary statements.

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SELECTED HISTORICAL FINANCIAL INFORMATION

The following tables show summarized historical financial data for Berkshire Hills and Legacy. You should read this summary financial information in connection with Berkshire Hills’ historical financial information, which is incorporated by reference into this document, and in connection with Legacy’s historical financial information, which is incorporated by reference into this document.

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SELECTED HISTORICAL FINANCIAL AND OTHER DATA OF
BERKSHIRE HILLS BANCORP, INC.

		At December 31,
(In thousands, except per share data)		2010				2009				2008				2007				2006
Selected Financial Data:
Total assets		$	2,880,716			$	2,700,424			$	2,666,729			$	2,513,432			$	2,149,642
Loans(1)			2,142,162				1,961,658				2,007,152				1,944,016				1,698,987
Allowance for loan losses			(31,898	)			(31,816	)			(22,908	)			(22,116	)			(19,370	)
Securities			405,953				420,966				341,516				258,497				234,174
Goodwill and other intangible assets			173,079				176,100				178,830				182,452				121,341
Total deposits			2,204,441				1,986,762				1,829,580				1,822,563				1,521,938
Borrowings and subordinated debentures			260,301				306,668				374,621				349,938				360,469
Total stockholders’ equity			387,960				384,581				408,425				326,837				258,161
Non-performing loans			13,712				38,700				12,171				10,508				7,592

		For the Years Ended December 31,
		2010				2009				2008				2007				2006
Selected Operating Data:
Total interest and dividend income		$	112,277			$	115,476			$	133,211			$	131,944			$	118,051
Total interest expense			35,330				45,880				57,471				68,019				57,811
Net interest income			76,947				69,596				75,740				63,925				60,240
Service charges and fee income			29,859				28,181				30,334				26,654				13,539
All other non-interest income (loss)			1,300				808				1,261				(2,011	)			(1,491	)
Total non-interest income			31,159				28,989				31,595				24,643				12,048
Total net revenue			108,106				98,585				107,335				88,568				72,288
Provision for loan losses			8,526				47,730				4,580				4,300				7,860
Total non-interest expense			81,729				78,571				71,699				65,494				48,868
Income tax expense (benefit) – continuing operations			4,113				(11,649	)			8,812				5,239				4,668
Net income from discontinued operations			—				—				—				—				371
Net income (loss)			13,738				(16,067	)			22,244				13,535				11,263
Less: Cumulative preferred stock dividends and accretion			—				1,030				—				—				—
Less: Deemed dividend from preferred stock repayment			—				2,954				—				—				—
Net income (loss) available to common stockholders		$	13,738			$	(20,051	)		$	22,244			$	13,535			$	11,263

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		At or For the Years Ended December 31,
		2010				2009				2008				2007				2006
Selected Operating Ratios and Other Data:
Performance Ratios:
Return (loss) on average assets(2)			0.50	%			(0.60	)%			0.87	%			0.60	%			0.53	%
Return (loss) on average equity(3)			3.54				(3.90	)			6.47				4.69				4.40
Net interest rate spread (tax equivalent)(4)			3.00				2.61				3.06				2.79				2.81
Net interest margin (tax equivalent)(5)			3.27				3.00				3.44				3.26				3.24
Non-interest income/total net revenue			28.82				29.41				29.44				27.82				16.67
Non-interest expense/average assets			2.97				2.93				2.81				2.90				2.31
Efficiency ratio(6)			70.59				73.39				64.40				62.94				58.46
Capital Ratios:
Average equity/average assets			14.11				15.36				13.49				12.73				12.08
Equity/total assets			13.47				14.24				15.32				13.00				12.01
Tier 1 capital to average assets – Berkshire Bank			8.02				7.86				9.34				7.97				7.69
Total capital to risk-weighted assets – Berkshire Bank			10.58				10.71				12.28				10.40				10.27
Asset Quality Ratios:
Nonperforming assets/total assets			0.59				1.43				0.48				0.45				0.35
Nonperforming loans/total loans			0.64				1.97				0.61				0.54				0.45
Net loans charged-off/average total loans			0.42				1.96				0.19				0.34				0.07
Allowance for loan losses/nonperforming loans			233				82				188				210				255
Allowance for loan losses as a percent of loans			1.49				1.62				1.14				1.14				1.14
Share Data:
Basic earnings per common share		$	0.99			$	(1.52	)		$	2.08			$	1.47			$	1.32
Diluted earnings per common share			0.99				(1.52	)			2.06				1.44				1.29
Dividends per common share			0.64				0.64				0.63				0.58				0.56
Book value per share			27.56				27.64				30.33				31.15				29.63
Market price at year end			22.11				20.68				30.86				26.00				33.46
Weighted average common shares outstanding – basic (thousands)			13,862				13,189				10,700				9,223				8,538
Weighted average common shares outstanding – diluted (thousands)			13,896				13,189				10,791				9,370				8,730

Note: All performance ratios are based on average balance sheet amounts where applicable.

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SELECTED HISTORICAL FINANCIAL AND OTHER DATA OF LEGACY BANCORP, INC.

		At or For the Years Ended December 31,
(In thousands, except per share data)		2010				2009				2008				2007				2006
Selected Financial Data:
Total assets		$	916,877			$	946,265			$	944,657			$	924,541			$	808,318
Loans, net(1)			610,941				653,334				695,264				654,024				578,802
Securities and other investments:			202,331				184,716				152,639				152,054				176,132
Deposits			685,245				651,378				608,088				610,447				518,248
Federal Home Loan Bank advances			105,388				160,352				197,898				167,382				127,438
Repurchase agreements			5,329				6,386				5,238				4,055				5,575
Total stockholders' equity			111,559				121,367				124,142				133,092				149,997
Nonperforming loans			12,744				19,578				7,549				1,532				879
Selected Operating Data:
Total interest and dividend income		$	40,964			$	45,818			$	50,327			$	49,357			$	43,915
Total interest expense			14,558				18,348				22,465				25,511				20,339
Net interest income			26,406				27,470				27,862				23,846				23,576
Provision for loan losses			10,468				4,883				1,465				1,051				233
Net interest income after provision for loan losses			15,938				22,587				26,397				22,795				23,343
Non-interest income:
Service charges and fees			5,108				4,006				4,541				4,496				4,044
Gain (loss) on sales or impairment of securities, net			(1,846	)			(10,267	)			(3,194	)			510				(1,736	)
Gain on sale of loans			607				860				255				270				210
FHLB prepayment restructuring charge			(1,481	)			—				—				—				—
Gain on curtailment and termination of defined benefit plan			—				—				—				—				605
Other			805				788				805				610				329
Total non-interest income (loss)			3,193				(4,613	)			2,407				5,886				3,452
Total non-interest expense			31,043				28,832				26,584				27,187				21,336
Income (loss) before income taxes			(11,912	)			(10,858	)			2,220				1,494				5,459
Provision (benefit) for income taxes		$	(4,016	)		$	(3,060	)		$	776			$	249			$	2,653
Net income (loss)			(7,896	)			(7,798	)			1,444				1,245				2,806

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		At or For the Years Ended December 31,
		2010				2009				2008				2007				2006
Selected Operating Ratios and Other Data:
Performance Ratios:
Return (loss) on average assets(2)			(0.84	)%			(0.82	)%			0.16	%			0.15	%			0.36	%
Return (loss) on average equity(3)			(6.48	)			(6.20	)			1.11				0.88				1.92
Net interest rate spread(4)			2.79				2.78				2.80				2.26				2.39
Net interest margin(5)			3.05				3.13				3.27				3.01				3.15
Efficiency ratio(6)			96.10				84.90				77.50				93.00				74.2
Non-interest expense to average assets			3.29				3.04				2.89				3.23				2.70
Dividend payout ratio			n/a				n/a				111.61				113.82				40.88
Capital Ratios:
Equity to total assets(7)			12.2	%			12.8	%			13.1	%			14.4	%			18.6	%
Average equity to average assets(7)			12.9				13.3				14.1				16.9				18.5
Total capital to risk-weighted assets – Bank			12.0				12.3				13.0				13.9				18.9
Asset Quality Ratios:
Nonperforming assets/total assets			1.63	%			2.20	%			0.80	%			0.17	%			0.11	%
Nonperforming loans/total loans			2.07				2.96				1.08				0.23				0.15
Allowance for loan losses/nonperforming loans			70.70				56.64				87.99				363.45				532.08
Allowance for loan losses/total loans			1.47				1.67				0.95				0.85				0.80
Share Data:
Earnings (loss per share)		$	(0.99	)		$	(0.98	)		$	0.18			$	0.14			$	0.29
Dividends per share		$	0.20			$	0.20			$	0.20			$	0.16			$	0.12
Book value per share – end of year		$	12.92			$	13.89			$	14.14			$	14.40			$	14.55
Market price at year end			13.14				9.86				10.68				13.26				15.85

n/a = Not Applicable

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UNAUDITED PRO FORMA COMBINED CONDENSED CONSOLIDATED FINANCIAL
INFORMATION RELATING TO THE ROME AND LEGACY MERGERS

The unaudited pro forma combined condensed consolidated financial information has been prepared using the acquisition method of accounting, giving effect to the merger of Berkshire Hills with Rome and the proposed merger with Legacy. The unaudited pro forma combined condensed consolidated statement of financial condition combines the historical financial information of Berkshire Hills, Rome, and Legacy as of December 31, 2010 and assumes that the mergers were completed on that date. The unaudited pro forma combined condensed consolidated statements of operations combine the historical financial information of Berkshire Hills, Rome, and Legacy and give effect to the mergers as if they had been completed as of January 1, 2010. The unaudited pro forma combined condensed consolidated financial information is presented for illustrative purposes only and is not necessarily indicative of the results of operations or financial condition had the mergers been completed on the dates described above, nor is it necessarily indicative of the results of operations in future periods or the future financial position of the combined entities. The financial information should be read in conjunction with the accompanying Notes to the Unaudited Pro Forma Combined Condensed Consolidated Financial Information. Certain reclassifications have been made to Rome's and Legacy’s historical financial information in order to conform to Berkshire Hills' presentation of financial information.

The actual value of Berkshire Hills common stock to be recorded as consideration in these mergers will be based on the closing price of Berkshire Hills common stock at the time of the merger completion dates. The merger with Rome was completed prior to the start of business on April 1, 2011; the closing price of Berkshire Hills’ stock on March 31, 2011 was $20.83, and that price was used to value Berkshire Hills’ stock. The proposed merger with Legacy is targeted for completion in the third quarter of 2011. There can be no assurance that the Legacy merger will be completed as anticipated. For purposes of the pro forma financial information, the fair value of Berkshire Hills common stock to be issued in connection with the Legacy merger was based on the $20.75 average closing price of the stock for the ten day period ending December 15, 2010, which was shortly prior to the date of the execution of the Agreement and Plan of Merger on December 21, 2010.

The pro forma financial information includes estimated adjustments, including adjustments to record assets and liabilities of Rome and Legacy at their respective fair values and represents the pro forma estimates by Berkshire Hills based on available fair value information as of the dates of the respective Agreements and Plans of Merger. In some cases, where noted, more recent information has been used to support estimated adjustments in the pro forma financial information.

The pro forma adjustments included herein are subject to change depending on changes in interest rates and the components of assets and liabilities and as additional information becomes available and additional analyses are performed. The final allocation of the purchase price for each merger will be determined after each merger is completed and after completion of thorough analyses to determine the fair value of Rome’s and Legacy’s tangible and identifiable intangible assets and liabilities as of the dates the mergers are completed. Increases or decreases in the estimated fair values of the net assets as compared with the information shown in the unaudited pro forma combined condensed consolidated financial information may change the amount of the purchase price allocated to goodwill and other assets and liabilities and may impact Berkshire Hills’ statement of operations due to adjustments in yield and/or amortization of the adjusted assets or liabilities. Any changes to Rome’s or Legacy’s stockholders’ equity, including results of operations from December 31, 2010 through the dates the mergers are completed, will also change the purchase price allocation, which may include the recording of a lower or higher amount of goodwill. The final adjustments may be materially different from the unaudited pro forma adjustments presented herein.

Berkshire Hills anticipates that the mergers with Rome and Legacy will provide the combined company with financial benefits that include reduced operating expenses. Berkshire Hills expects to realize cost savings approximating 35% of the anticipated non-interest expense of Rome and approximating 42% of the anticipated non-interest expense of Legacy These cost savings are not included in these pro forma statements and there can be no assurance that expected cost savings will be realized. The pro forma information, while helpful in illustrating the financial characteristics of the combined company under one set of assumptions, does not reflect the benefits of expected cost savings or opportunities to earn additional revenue and, accordingly, does

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not attempt to predict or suggest future results. It also does not necessarily reflect what the historical results of the combined company would have been had our companies been combined during these periods.

The unaudited pro forma combined condensed consolidated financial information has been derived from and should be read in conjunction with the historical consolidated financial statements and the related notes of Berkshire Hills, Rome, and Legacy, which are incorporated in this joint proxy statement/prospectus by reference. See “Where You Can Find More Information” on page 96.

The unaudited pro forma stockholders’ equity and net income are qualified by the statements set forth under this caption and should not be considered indicative of the market value of Berkshire Hills common stock or the actual or future results of operations of Berkshire Hills for any period. Actual results may be materially different than the pro forma information presented.

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Unaudited Pro Forma Combined Condensed Consolidated Statement of Financial Condition
As of December 31, 2010

						Rome Merger												Legacy Merger												Legacy Deposit				Pro Forma Combined Berkshire/ Rome/Legacy w/Divest
(In thousands)		Berkshire				Rome				Pro Forma Merger Adjustments				Berkshire/ Rome Pro Forma				Legacy				Pro Forma Merger Adjustments				Berkshire/ Rome/ Legacy Pro Forma				Divestiture Pro Forma Amount Divested(16)
Assets
Cash and cash equivalents		$	44,140			$	18,805			$	(6,986	)(1)		$	55,959			$	27,092			$	(9,253	)(1)		$	73,798			$	3,300			$	77,098
Securities			405,953				17,871				(22,077	)(2)			401,747				202,331				(21,950	)(2)			582,128				(40,000	)			542,128
Total loans			2,142,162				269,347				(5,239	)(3)			2,406,270				616,112				(22,300	)(3)			3,000,082				(120,000	)			2,880,082
Less: Allowance for loan losses			(31,898	)			(2,490	)			2,595	(3)			(31,793	)			(9,010	)			9,375	(3)			(31,428	)			—				(31,428	)
Net loans			2,110,264				266,857				(2,644	)			2,374,477				607,102				(12,925	)			2,968,654				(120,000	)			2,848,654
Goodwill			161,725				—				14,364	(4)			176,089				11,558				10,808	(4)			198,455				—				198,455
Other identifiable intangible assets			11,354				—				5,208	(5)			16,562				3,625				14,923	(5)			35,110				(3,600	)			31,510
Total intangible assets			173,079				—				19,572				192,651				15,183				25,731				233,565				(3,600	)			229,965
Other assets			147,280				23,678				1,771	(6)			172,729				65,169				10,046	(6)			247,944				(500	)			247,444
Total assets		$	2,880,716			$	327,211			$	(10,364	)		$	3,197,563			$	916,877			$	(8,351	)		$	4,106,089			$	(160,800	)		$	3,945,289
Liabilities
Total deposits		$	2,204,441			$	225,325			$	528	(7)		$	2,430,294			$	685,245			$	5,207	(7)		$	3,120,746				(162,000	)			2,958,746
Total borrowings			260,301				35,661				1,397	(8)			297,359				110,717				11,442	(8)			419,518				—				419,518
Other liabilities			28,014				5,570				—				33,584				9,356				—				42,940				—				42,940
Total liabilities			2,492,756				266,556				1,925				2,761,237				805,318				16,649				3,583,204				(162,000	)			3,421,204
Total stockholders' equity			387,960				60,655				(12,289	)(9)			436,326				111,559				(25,000	)(9)			522,885				1,200				524,085
Total liabilities and stockholders' equity		$	2,880,716			$	327,211			$	(10,364	)		$	3,197,563			$	916,877			$	(8,351	)		$	4,106,089			$	(160,800	)		$	3,945,289

 
 
The accompanying notes are an integral part of these consolidated financial statements.

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Unaudited Pro Forma Combined Condensed Consolidated Statement of Operations
For the Fiscal Year Ended December 31, 2010

						Rome Merger												Legacy Merger								Pro forma Combined Berkshire/ Rome/Legacy				Legacy Deposit				Pro Forma Combined Berkshire/ Rome/Legacy w/Divest
(In thousands, except per share data)		Berkshire Historical				Rome Historical				Pro forma Merger Adjustments				Pro forma Combined Berkshire/ Rome				Legacy Historical				Pro forma Merger Adjustments								Divestiture Pro forma Amount Divested(16)
Interest and dividend income
Loans		$	98,359			$	15,968			$	612	(10)		$	114,939			$	36,014			$	2,128	(10)		$	153,081			$	(7,200	)		$	145,881
Securities and other			13,918				719				(194	)(10)			14,443				4,950				—	(10)			19,393				(1,200	)			18,193
Total interest and dividend income			112,277				16,687				418				129,382				40,964				2,128				172,474				(8,400	)			164,074
Interest expense
Deposits			26,316				1,826				(352	)(10)			27,790				8,928				(4,166	)(10)			32,552				(1,782	)			30,770
Borrowings			9,014				1,191				(698	)(10)			9,507				5,630				(4,577	)(10)			10,560				—				10,560
Total interest expense			35,330				3,017				(1,050	)			37,297				14,558				(8,743	)			43,112				(1,782	)			41,330
Net interest income			76,947				13,670				1,468				92,085				26,406				10,871				129,362				(6,618	)			122,744
Total non-interest income			31,159				3,350				—	(11)			34,509				3,193				—	(11)			37,702				(324	)			37,378
Total net revenue			108,106				17,020				1,468				126,594				29,599				10,871				167,064				(6,942	)			160,122
Provision for loan losses			8,526				1,796				—	(12)			10,322				10,468				—	(12)			20,790				—				20,790
Total non-interest expense			81,729				11,861				1,490	(13)			95,080				31,043				3,355	(13)			129,478				(1,782	)			127,696
Income (loss) before income taxes			17,851				3,363				(22	)			21,192				(11,912	)			7,516				16,796				(5,160	)			11,636
Income tax expense (benefit)			4,113				1,102				(9	)(14)			5,206				(4,016	)			3,119	(14)			4,309				(2,141	)			2,168
Net income (loss)		$	13,738			$	2,261			$	(13	)		$	15,986			$	(7,896	)		$	4,397			$	12,487			$	(3,019	)		$	9,468
Earnings (loss) per common share:
Basic		$	0.99			$	0.35							$	0.97			$	(0.99	)						$	0.60							$	0.45
Diluted		$	0.99			$	0.35							$	0.97			$	(0.99	)						$	0.60							$	0.45
Weighted average common shares outstanding:
Basic			13,862				6,523				(3,926	)(15)			16,459				7,990				(3,639	)(15)			20,810				—				20,810
Diluted			13,896				6,523				(3,926	)(15)			16,493				7,990				(3,639	)(15)			20,844				—				20,844

 
 
The accompanying notes are an integral part of these consolidated financial statements.

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NOTES TO THE UNAUDITED PRO FORMA COMBINED CONDENSED CONSOLIDATED
FINANCIAL INFORMATION

Note A — Basis of Presentation

The unaudited pro forma combined condensed consolidated financial information and explanatory notes show the impact on the historical financial condition and income of Berkshire Hills resulting from the Rome merger and the proposed Legacy merger under the acquisition method of accounting. Under the acquisition method of accounting, the assets and liabilities of Rome and Legacy are recorded by Berkshire Hills at their respective fair values as of the date each merger is completed. The unaudited pro forma combined condensed consolidated statement of financial condition combines the historical financial information of Berkshire Hills, Rome, and Legacy as of December 31, 2010, and assumes that the mergers were completed on that date. The unaudited pro forma combined condensed consolidated statement of operations gives effect to the Rome merger and the proposed Legacy merger as if both mergers had been completed on January 1, 2010.

As the mergers are recorded using the acquisition method of accounting, all loans are recorded at fair value, including adjustments for credit, and no allowance for loan losses is carried over to Berkshire Hills’ statement of financial condition. In addition, certain anticipated nonrecurring costs associated with the mergers such as severance, professional fees, legal fees, and conversion related expenditures are not reflected in the pro forma statements of operations.

While the recording of the acquired loans at their fair value will impact the prospective determination of the provision for loan losses and the allowance for loan losses, for purposes of the unaudited pro forma combined condensed consolidated statement of operations for the year ended December 31, 2010, we assumed no adjustments to the historical amount of Rome’s or Legacy’s provision for loan losses. If such adjustments were estimated, there could be a reduction, which could be significant, to the historical amounts of Rome’s or Legacy’s provision for loan losses presented.

Note B — Accounting Policies and Financial Statement Classifications

The accounting policies of Rome and Legacy are in the process of being reviewed in detail by Berkshire Hills. On completion of such review, conforming adjustments or financial statement reclassifications may be determined.

Note C — Merger and Acquisition Integration Costs

The plans to integrate the operations of Berkshire Hills with those of Rome and Legacy are still being developed. The specific details of these plans will continue to be refined over the next several months, and will include assessing personnel, benefit plans, premises, equipment, and service contracts to determine where there may be potential advantage in eliminating redundancies. Certain decisions arising from these assessments may involve involuntary termination of employees, vacating leased premises, changing information systems, canceling contracts with certain service providers and selling or otherwise disposing of certain premises, furniture and equipment. Berkshire Hills expects to incur merger related costs including professional fees, legal fees, system conversion costs, and costs related to communications with customers and others. To the extent there are costs associated with these actions, the costs will be recorded based on the nature of the cost and timing of these integration actions.

Note D — Estimated Annual Cost Savings

Berkshire Hills expects to realize annualized cost savings of approximately $3.8 million (35%) of Rome’s expected non-interest expense and $11.1 million (42%) of Legacy’s expected non-interest expenses following the mergers. Berkshire Hills expects to achieve approximately 75% of the anticipated annualized savings related to Rome in 2011 and 100% of the anticipated annualized savings thereafter. Berkshire Hills expects to achieve approximately 25% of the anticipated annualized savings related to Legacy in 2011 and 100% of the anticipated annualized savings thereafter. These cost savings are not reflected in the pro forma financial information and there can be no assurance they will be achieved in the amount or manner currently contemplated.

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NOTES TO THE UNAUDITED PRO FORMA COMBINED CONDENSED CONSOLIDATED
FINANCIAL INFORMATION

Note E — Divestiture of Deposits of Legacy

The merger with Legacy is expected to require a divestiture of deposits in order to satisfy federal regulations. The actual amount of the deposits to be divested (if any) will be determined by federal regulatory authorities during the merger approval process and may differ materially from the amount included herein. The pro forma statement of financial condition includes estimated adjustments to reflect the impact of the deposit divestiture. Berkshire Hills anticipates that $162 million in deposits will be divested through the sale of certain Legacy branches. Berkshire Hills also expects to sell $120 million in loans and $40 million in securities, along with $2 million in other assets. It is estimated that the deposits would be sold at a 3.5% premium and that the loans would be sold at par. Net of the writedown of the related core deposit intangible asset, it is estimated that a net after-tax gain of $1.2 million will be recorded as a result of the divestiture. This gain is recorded in the pro forma statement of financial condition as an adjustment to equity. The divestiture would reduce annualized interest income at an assumed amount equivalent to approximately 6.0% of the sold loans and 3.0% of the divested investment securities. Interest expense is assumed to be reduced by approximately 1.10% of the divested deposits. Non-interest income is assumed to decrease by approximately 0.2% of the divested deposits, and non-interest expense is assumed to decrease by approximately 1.1% of the divested deposits. The resulting annualized anticipated reduction in income would approximate $5.2 million on a pre-tax basis and $3.0 million after tax. These impacts on operating income have been separately included in the pro forma income statement. Actual divestiture amounts and related impacts may differ materially from those contemplated herein.

Note F — Pro Forma Adjustments

The following pro forma adjustments have been reflected in the unaudited pro forma combined condensed consolidated financial information. All adjustments are based on current assumptions and valuations, which are subject to change.

The actual one-time expenses charged against income will be charged in some cases against the income of the acquired banks and in some cases against Berkshire Hills’ income. The allocation of these amounts has not yet been fully determined. In these pro forma financial statements, it is assumed that all such expenses will be recorded against Berkshire Hills’ income, and they are represented as a pro forma charge against equity on the merger date. Those expenses which are actually charged against income of the acquired banks will result in a charge to goodwill, rather than to Berkshire Hills’ equity.

Most of the adjustments in these pro forma financial statements were based on due diligence analysis performed by Berkshire Hills on the financial condition of Rome and Legacy based on information in the third and fourth quarters of 2010. All three of the companies recorded certain charges in the fourth quarter of 2010 which included amounts which were contained in the assumptions supporting adjustments to the pro forma financial statements. In addition to one-time merger related expenses, these amounts included loan loss provisions, securities writedowns, and borrowings prepayment penalties. The total amount of these net charges was estimated at $6.0 million after-tax. In order to avoid double counting these amounts, a $6.0 million credit to equity and debit to cash is included among the pro forma adjustments in the pro forma statement of financial condition as of December 31, 2010.

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NOTES TO THE UNAUDITED PRO FORMA COMBINED CONDENSED CONSOLIDATED
FINANCIAL INFORMATION

Note F — Pro Forma Adjustments  – (continued)

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NOTES TO THE UNAUDITED PRO FORMA COMBINED CONDENSED CONSOLIDATED
FINANCIAL INFORMATION

Note F — Pro Forma Adjustments  – (continued)

Equity and Goodwill Adjustment Detail For Rome:
Equity adjustment
Fair value of Berkshire Hills common shares issued		$	54,099	(a)
Elimination of Rome stockholders’ equity			(60,655	)
After tax integration expenses charged against cash and equivalents			(5,733	)
Total stockholders’ equity adjustment		$	(12,289	)
Goodwill adjustment
Fair value of Berkshire Hills common shares issued for Rome common shares		$	54,099	(a)
Cash payments to Rome stockholders			22,132	(b)
Value of Rome options			354	(c)
Total consideration		$	76,585
Carrying value of Rome net assets at December 31, 2010		$	60,655
Fair value adjustments (debit/(credit))
Investment securities			583
Loans, net			(2,644	)
Other identifiable intangible assets – core deposit intangible			5,208
Certificates of deposit			(528	)
Borrowings			(1,396	)
Other assets			1,200
Net adjustments to deferred tax assets			(857	)
Total fair value adjustments			1,566
Fair value of net assets acquired at December 31, 2010			62,221
Excess of consideration paid over fair value of net assets acquired (goodwill)			14,364
Elimination of Rome goodwill			—
Net goodwill adjustment		$	14,364

Rome common shares outstanding as of April 1, 2011
Issued			9,896
Less treasury shares			(3,118	)
Less unallocated ESOP shares repurchased to treasury to repay ESOP loan			(161	)
Less Rome shares owned by Berkshire Hills cancelled per merger agreement			(59	)
Outstanding Rome shares exchanged for Berkshire Hills consideration			6,558
Stock portion of consideration			70	%
Outstanding Rome shares exchanged for Berkshire Hills stock consideration			4,590
Multiplied by exchange ratio			0.5658
Berkshire Hills common shares issued to Rome shareholders			2,597
Closing price per share of Berkshire Hills stock on March 31, 2011		$	20.83
Fair value of Berkshire Hills common shares issued for Rome common shares		$	54,099

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NOTES TO THE UNAUDITED PRO FORMA COMBINED CONDENSED CONSOLIDATED
FINANCIAL INFORMATION

Note F — Pro Forma Adjustments  – (continued)

Outstanding Rome shares exchanged for Berkshire Hills consideration			6,558
Cash portion of consideration			30	%
Outstanding Rome shares exchanged for Berkshire Hills cash consideration			1,967
Cash value per share exchanged		$	11.25
Total cash consideration for Rome common shares		$	22,132

Equity and Goodwill Adjustment Detail For Legacy:
Equity adjustment
Fair value of Berkshire Hills common shares to be issued		$	90,288	(a)
Fair value of Legacy stock options converted to Berkshire Hills options			1,070	(c)
Gain on Legacy stock owned by Berkshire Hills, recorded in income			1,451	(d)
Elimination of Legacy stockholders’ equity			(111,559	)
After tax integration expenses charged against cash and equivalents			(12,250	)
After tax adjustment for total pro forma charges recorded in the fourth quarter of 2010			6,000
Total stockholders’ equity adjustment		$	(25,000	)
Goodwill adjustment
Fair value of Berkshire Hills common shares to be issued		$	90,288	(a)
Cash payments to Legacy stockholders			10,032	(b)
Fair value of Legacy stock options converted to Berkshire Hills options			1,070	(c)
Cash payments for Legacy stock options being canceled			1,269	(c)
Cost of Legacy shares previously purchased by Berkshire Hills			3,640	(d)
Gain on Legacy stock owned by Berkshire Hills, recorded in income			1,451	(d)
Total consideration		$	107,750
Carrying value of Legacy net assets at December 31, 2010		$	111,559
Fair value adjustments (debit/(credit))
Write off of Legacy goodwill			(11,558	)
Write off of Legacy other identifiable intangibles			(3,625	)
Investment securities			(7,000	)
Loans, net			(12,925	)
Other identifiable intangible assets			18,548
Certificates of deposit			(5,207	)
Borrowings			(11,442	)
Other assets			7,000
Net adjustments to deferred tax assets			34
Total fair value adjustments			(26,175	)
Fair value of net assets acquired at December 31, 2010		$	85,384
Excess of consideration paid over fair value of net assets acquired (goodwill)		$	22,366
Elimination of Legacy goodwill			(11,558	)
Net goodwill adjustment		$	10,808

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NOTES TO THE UNAUDITED PRO FORMA COMBINED CONDENSED CONSOLIDATED
FINANCIAL INFORMATION

Note F — Pro Forma Adjustments  – (continued)

Legacy common shares outstanding as of December 31, 2010
Issued			10,309
Less treasury shares			(1,677	)
Less pro forma unallocated ESOP shares to be rescinded as a result of the merger			(523	)
Less Legacy shares owned by Berkshire Hills			(392	)
Pro forma outstanding Legacy shares to be exchanged for Berkshire Hills consideration			7,717
Multiplied by exchange ratio			0.56385
Berkshire Hills common shares to be issued			4,351
Average closing price per share of Berkshire Hills stock for ten days ended December 15, 2010		$	20.75
Fair value of Berkshire Hills common shares to be issued		$	90,288

Pro forma outstanding Legacy shares to be exchanged for Berkshire Hills consideration			7,717
Cash consideration per share of outstanding Legacy shares		$	1.30
Total cash consideration		$	10,032

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NOTES TO THE UNAUDITED PRO FORMA COMBINED CONDENSED CONSOLIDATED
FINANCIAL INFORMATION

Note F — Pro Forma Adjustments  – (continued)

Note G — Effect of Hypothetical Adjustments on Rome’s and Legacy’s Historical Financial Statements

The unaudited pro forma combined condensed consolidated statement of operations presents the pro forma results assuming both the Rome and Legacy mergers occurred on January 1, 2010. As required by Regulation S-X Article 11, the pro forma statement of operations does not reflect any adjustments to eliminate Rome’s or Legacy’s historical provision for credit losses.

Both Rome’s and Legacy’s provision for credit losses for the periods presented relate to loans that Berkshire Hills is required to initially record at fair value. Such fair value adjustments include a component related to the expected credit losses on those loan portfolios. Berkshire Hills believes that these provisions would not have been recorded in Berkshire Hills’ combined consolidated financial statements for the periods presented had the mergers been completed on January 1, 2010.

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COMPARATIVE PRO FORMA PER SHARE DATA

The following table summarizes selected share and per share information about Berkshire Hills, Rome, and Legacy giving effect to the mergers (which we refer to as “pro forma” information). The data in the table should be read together with the financial information and the financial statements of Berkshire Hills, Rome, and Legacy incorporated by reference or included in this proxy statement/prospectus. The pro forma information is presented as an illustration only. The data does not necessarily indicate the combined financial position per share or combined results of operations per share that would have been reported if the mergers had occurred when indicated, nor is the data a forecast of the combined financial position or combined results of operations for any future period.

The information about book value per share and shares outstanding assumes that the mergers took place as of December 31, 2010 and is based on the assumptions set forth in the preceding unaudited pro forma combined consolidated statements of financial condition. The information about dividends and earnings per share assumes that the mergers took place as of January 1, 2010 and is based on the assumptions set forth in the preceding unaudited pro forma combined consolidated statements of operations. No pro forma adjustments have been included in these statements of operations which reflect potential effects of the mergers related to integration expenses, cost savings or operational synergies which are expected to be obtained by combining the operations of Berkshire Hills, Rome, and Legacy, or the costs of combining the companies and their operations. It is further assumed that Berkshire Hills will pay a cash dividend after the completion of the merger at the annual rate of $0.64 per share. The actual payment of dividends is subject to numerous factors, and no assurance can be given that Berkshire Hills will pay dividends following the completion of the merger or that dividends will not be reduced in the future.

(Shares and Stockholders' Equity in thousands)		Berkshire				Rome				Berkshire/Rome Pro Forma Combined				Legacy				Berkshire/Rome/ Legacy w/divestiture Pro Forma Combined				Pro Forma Legacy Equivalent Shares
Book value per share:
December 31, 2010		$	27.56			$	8.95			$	26.17			$	12.92			$	24.93			$	14.06
Cash dividends paid per common share:
Year ended December 31, 2010		$	0.64			$	0.36			$	0.64			$	0.20			$	0.64			$	0.36
Basic earnings (loss) per share from continuing operations:
Year ended December 31, 2010		$	0.99			$	0.35			$	0.97			$	(0.99	)		$	0.45			$	0.25
Diluted earnings (loss) per share from continuing operations:
Year ended December 31, 2010		$	0.99			$	0.35			$	0.97			$	(0.99	)		$	0.45			$	0.25
Note:
Shares outstanding:
December 31, 2010			14,076				6,778				16,673				8,632				21,024
Stockholders' Equity
December 31, 2010		$	387,960			$	60,655			$	436,326			$	111,559			$	524,085

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MARKET PRICE AND DIVIDEND INFORMATION

Berkshire Hills common stock is listed on the NASDAQ Global Select Market under the symbol “BHLB.” Legacy common stock is quoted on the NASDAQ Global Market under the symbol “LEGC.” The following table lists the high and low prices per share for Berkshire Hills common stock and Legacy common stock and the cash dividends declared by each company for the periods indicated.

		Berkshire Hills Bancorp, Inc. Common Stock												Legacy Bancorp, Inc. Common Stock
		High				Low				Dividends				High				Low				Dividends
Quarter Ended
March 31, 2011		$	22.92			$	20.68			$	0.16			$	13.75			$	12.61			$	0.05
December 31, 2010		$	22.49			$	17.90			$	0.16			$	13.14			$	7.49			$	0.05
September 30, 2010		$	20.94			$	17.08			$	0.16			$	8.91			$	7.55			$	0.05
June 30, 2010		$	22.84			$	16.81			$	0.16			$	9.73			$	8.24			$	0.05
March 31, 2010		$	20.99			$	16.20			$	0.16			$	9.98			$	9.01			$	0.05
December 31, 2009		$	22.85			$	18.05			$	0.16			$	11.07			$	9.40			$	0.05
September 30, 2009		$	24.88			$	19.92			$	0.16			$	13.46			$	10.50			$	0.05
June 30, 2009		$	26.99			$	19.87			$	0.16			$	12.10			$	9.29			$	0.05
March 31, 2009		$	31.39			$	18.46			$	0.16			$	11.21			$	7.90			$	0.05

You should obtain current market quotations for Berkshire Hills and Legacy common stock, as the market price of Berkshire Hills common stock will fluctuate between the date of this document and the date on which the Merger is completed, and thereafter. You can get these quotations from a newspaper, on the Internet or by calling your broker.

As of May 2, 2011, there were approximately 2,691 holders of record of Berkshire Hills common stock. As of May 2, 2011, there were approximately 919 holders of record of Legacy common stock. These numbers do not reflect the number of persons or entities who may hold their stock in nominee or “street name” through brokerage firms.

Following the Merger, the declaration of dividends will be at the discretion of Berkshire Hills’ board of directors and will be determined after consideration of various factors, including earnings, cash requirements, the financial condition of Berkshire Hills, applicable state law and government regulations and other factors deemed relevant by Berkshire Hills’ board of directors.

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SPECIAL MEETING OF LEGACY BANCORP, INC. STOCKHOLDERS

Date, Place, Time and Purpose

Legacy’s board of directors is sending you this document to request that you allow your shares of Legacy to be represented at the special meeting by the persons named in the enclosed proxy card. At the special meeting, the Legacy board of directors will ask you to vote on a proposal to approve the Merger Agreement. You may also be asked to vote to adjourn the special meeting if necessary to permit further solicitation of proxies if there are not sufficient votes at the time of the meeting to approve the Merger Agreement. The special meeting will be held at The Crowne Plaza Hotel, One West Street, Pittsfield, Massachusetts at 9:30 a.m., local time, on June 20, 2011.

Who Can Vote at the Meeting

You are entitled to vote if the records of Legacy showed that you held shares of Legacy common stock as of the close of business on May 2, 2011. As of the close of business on that date, a total of 8,631,732 shares of Legacy common stock were outstanding. Each share of common stock has one vote. If you are a beneficial owner of shares of Legacy common stock held by a broker, bank or other nominee (i.e., in “street name”) and you want to vote your shares in person at the meeting, you will have to get a written proxy in your name from the broker, bank or other nominee who holds your shares.

Quorum; Vote Required

The special meeting will conduct business only if a majority of the outstanding shares of Legacy common stock entitled to vote is represented in person or by proxy at the meeting. If you return valid proxy instructions or attend the meeting in person, your shares will be counted for purposes of determining whether there is a quorum, even if you abstain from voting. Broker non-votes also will be counted for purposes of determining the existence of a quorum. A broker non-vote occurs when a broker, bank or other nominee holding shares of Legacy common stock for a beneficial owner does not vote on a particular proposal because the nominee does not have discretionary voting power with respect to that item and has not received voting instructions from the beneficial owner.

Proposal 1: Approval of the Merger Agreement.  Approval of the Merger Agreement will require the affirmative vote of a majority of the outstanding shares of Legacy common stock entitled to vote at the meeting. Failure to return a properly executed proxy card or to vote in person will have the same effect as a vote against the Merger Agreement. Broker non-votes and abstentions from voting will have the same effect as voting against the Merger Agreement.

Proposal 2: Adjourn the meeting if necessary or appropriate, including an adjournment to permit further solicitation of proxies in favor of the Merger.  The affirmative vote of the majority of votes cast is required to approve the proposal to adjourn the meeting if necessary to permit further solicitation of proxies on the proposal to approve the Merger Agreement.

Shares Held by Legacy Officers and Directors and by Berkshire Hills

As of May 2, 2011, directors and executive officers of Legacy beneficially owned 360,386 shares of Legacy common stock, not including shares that may be acquired upon the exercise of stock options. This equals 4.2% of the outstanding shares of Legacy common stock. The directors and executive officers of Legacy have agreed to vote their shares in favor of the Merger at the special meeting. As of the same date, Berkshire Hills and its subsidiaries and its directors and executive officers owned approximately 392,600 shares of Legacy common stock. This equals 4.5% of the total outstanding shares of Legacy common stock.

Voting and Revocability of Proxies

You may vote in person at the special meeting or by proxy. To ensure your representation at the special meeting, Legacy recommends that you vote by proxy even if you plan to attend the special meeting. You can always change your vote at the special meeting.

Legacy stockholders whose shares are held in “street name” by their broker, bank or other nominee must follow the instructions provided by their broker, bank or other nominee to vote their shares. Your broker or bank may allow you to deliver your voting instructions via the telephone or the Internet.

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Voting instructions are included on your proxy form. If you properly complete and timely submit your proxy, your shares will be voted as you have directed. You may vote for, against, or abstain with respect to the approval of the Merger Agreement and the proposal to adjourn the meeting. If you are the record holder of your shares of Legacy common stock and submit your proxy without specifying a voting instruction, your shares of Legacy common stock will be voted “FOR” the proposal to adopt the Merger Agreement, “FOR” the proposal to approve the Parachute Arrangements and “FOR” the proposal to adjourn the meeting if necessary to permit further solicitation of proxies on the proposal to approve the Merger Agreement. Legacy’s board of directors recommends a vote “FOR” approval of the Merger Agreement and “FOR” approval of the proposal to adjourn the meeting if necessary to permit further solicitation of proxies on the proposal to approve the Merger Agreement.

You may revoke your proxy before it is voted by:

Attendance at the special meeting will not, in and of itself, constitute a revocation of a proxy. All written notices of revocation and other communication with respect to the revocation of proxies should be addressed to:

Legacy Bancorp, Inc.
Kimberly A. Mathews, Corporate Secretary and General Counsel
99 North Street
Pittsfield, Massachusetts 01201

If any matters not described in this document are properly presented at the special meeting, the persons named in the proxy card will use their own judgment to determine how to vote your shares. Legacy does not know of any other matters to be presented at the meeting.

Solicitation of Proxies

Legacy will pay for this proxy solicitation. In addition to soliciting proxies by mail, Phoenix Advisory Partners, LLC, a proxy solicitation firm, will assist Legacy in soliciting proxies for the special meeting. Legacy will pay $5,500, plus expenses, for these services. Legacy will, upon request, reimburse brokers, banks and other nominees for their expenses in sending proxy materials to their customers who are beneficial owners and obtaining their voting instructions. Additionally, directors, officers and employees of Legacy may solicit proxies personally and by telephone. None of these persons will receive additional or special compensation for soliciting proxies.

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SPECIAL MEETING OF BERKSHIRE HILLS BANCORP, INC. STOCKHOLDERS

Date, Place, Time and Purpose

Berkshire Hills’s board of directors is sending you this document to request that you allow your shares of Berkshire Hills to be represented at the special meeting by the persons named in the enclosed proxy card. At the special meeting, the Berkshire Hills board of directors will ask you to vote on a proposal to approve the Merger Agreement. You may also be asked to vote to adjourn the special meeting if necessary to permit further solicitation of proxies if there are not sufficient votes at the time of the meeting to approve the Merger Agreement. The special meeting will be held at The Crowne Plaza Hotel, One West Street, Pittsfield, Massachusetts at 11:00 a.m., local time, on June 20, 2011.

Who Can Vote at the Meeting

You are entitled to vote if the records of Berkshire Hills showed that you held shares of Berkshire Hills common stock as of the close of business on May 2, 2011. As of the close of business on that date, a total of 16,779,110 shares of Berkshire Hills common stock were outstanding. Each share of common stock has one vote. If you are a beneficial owner of shares of Berkshire Hills common stock held by a broker, bank or other nominee (i.e., in “street name”) and you want to vote your shares in person at the meeting, you will have to get a written proxy in your name from the broker, bank or other nominee who holds your shares.

Quorum; Vote Required

The special meeting will conduct business only if a majority of the outstanding shares of Berkshire Hills common stock entitled to vote is represented in person or by proxy at the meeting. If you return valid proxy instructions or attend the meeting in person, your shares will be counted for purposes of determining whether there is a quorum, even if you abstain from voting. Broker non-votes also will be counted for purposes of determining the existence of a quorum. A broker non-vote occurs when a broker, bank or other nominee holding shares of Berkshire Hills common stock for a beneficial owner does not vote on a particular proposal because the nominee does not have discretionary voting power with respect to that item and has not received voting instructions from the beneficial owner.

Proposal 1: Approval of the Merger Agreement.  Approval of the Merger Agreement will require the affirmative vote of a majority of the outstanding shares of Berkshire Hills common stock entitled to vote at the meeting. Failure to return a properly executed proxy card or to vote in person will have the same effect as a vote against the Merger Agreement. Broker non-votes and abstentions from voting will have the same effect as voting against the Merger Agreement.

Proposal 2: Approval of the amendment to the Berkshire Hills Bancorp, Inc. Certificate of Incorporation.  Under the Berkshire Hills Certificate of Incorporation and Bylaws and Delaware law, the amendment of Berkshire Hills Certificate of Incorporation requires a vote “FOR” the amendment by a majority of the outstanding Common Stock entitled to vote thereof.

Proposal 3: Adjourn the meeting if necessary or appropriate, including an adjournment to permit further solicitation of proxies in favor of the Merger.  The affirmative vote of the majority of votes cast is required to approve the proposal to adjourn the meeting if necessary to permit further solicitation of proxies on the proposal to approve the Merger Agreement.

Shares Held by Berkshire Hills Officers and Directors and by Berkshire Hills

As of May 2, 2011, directors and executive officers of Berkshire Hills beneficially owned 521,087 shares of Berkshire Hills common stock, not including shares that may be acquired upon the exercise of stock options. This equals approximately 3.1% of the outstanding shares of Berkshire Hills common stock. The directors and executive officers of Berkshire Hills have agreed to vote their shares in favor of the Merger at the special meeting. As of the same date, Legacy and its subsidiaries and its directors and executive officers did not own any shares of Berkshire Hills common stock.

Voting and Revocability of Proxies

You may vote in person at the special meeting or by proxy. To ensure your representation at the special meeting, Berkshire Hills recommends that you vote by proxy even if you plan to attend the special meeting. You can always change your vote at the special meeting.

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Berkshire Hills stockholders whose shares are held in “street name” by their broker, bank or other nominee must follow the instructions provided by their broker, bank or other nominee to vote their shares. Your broker or bank may allow you to deliver your voting instructions via the telephone or the Internet.

Voting instructions are included on your proxy form. If you properly complete and timely submit your proxy, your shares will be voted as you have directed. You may vote for, against, or abstain with respect to the approval of the Merger Agreement and the proposal to adjourn the meeting. If you are the record holder of your shares of Berkshire Hills common stock and submit your proxy without specifying a voting instruction, your shares of Berkshire Hills common stock will be voted “FOR” the proposal to adopt the Merger Agreement, “FOR” the amendment of the Berkshire Hills Certificate of Incorporation, and “FOR” the proposal to adjourn the meeting if necessary to permit further solicitation of proxies on the proposal to approve the Merger Agreement. Berkshire Hills’s board of directors recommends a vote “FOR” approval of the Merger Agreement, “FOR” the amendment of the Berkshire Hills Certificate of Incorporation, and “FOR” approval of the proposal to adjourn the meeting if necessary to permit further solicitation of proxies on the proposal to approve the Merger Agreement.

You may revoke your proxy before it is voted by:

Attendance at the special meeting will not, in and of itself, constitute a revocation of a proxy. All written notices of revocation and other communication with respect to the revocation of proxies should be addressed to:

Berkshire Hills Bancorp, Inc.
Wm. Gordon Prescott, Corporate Secretary and General Counsel
24 North Street
Pittsfield, Massachusetts 01201

If any matters not described in this document are properly presented at the special meeting, the persons named in the proxy card will use their own judgment to determine how to vote your shares. Berkshire Hills does not know of any other matters to be presented at the meeting.

Solicitation of Proxies

Berkshire Hills will pay for this proxy solicitation. In addition to soliciting proxies by mail, Phoenix Advisory Partners, LLC, a proxy solicitation firm, will assist Berkshire Hills in soliciting proxies for the special meeting. Berkshire Hills will pay $6,500, plus expenses, for these services. Berkshire Hills will, upon request, reimburse brokers, banks and other nominees for their expenses in sending proxy materials to their customers who are beneficial owners and obtaining their voting instructions. Additionally, directors, officers and employees of Berkshire Hills may solicit proxies personally and by telephone. None of these persons will receive additional or special compensation for soliciting proxies.

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RIGHTS OF DISSENTING LEGACY BANCORP, INC. STOCKHOLDERS

Under Delaware law, holders of Legacy common stock that do not wish to accept the Merger consideration may elect to have the value of their shares of Legacy common stock judicially determined and paid in cash, together with a fair rate of interest, if any. The valuation, which could be higher or lower than, or the same as, the value of the Merger Consideration, will exclude any element of value arising from the accomplishment or expectation of the Merger. A stockholder may only exercise such appraisal rights by complying with the provisions of Section 262 of the Delaware General Corporation Law.

The following summary of the provisions of Section 262 of the Delaware General Corporation Law is not a complete statement of the law pertaining to appraisal rights under the Delaware General Corporation Law and is qualified in its entirety by reference to the full text of Section 262 of the Delaware General Corporation Law, a copy of which is attached to this document as Appendix D and incorporated into this summary by reference. If you wish to exercise appraisal rights or wish to preserve your right to do so, you should carefully review Section 262 and are urged to consult a legal advisor before electing or attempting to exercise these rights.

All references in Section 262 and in this summary to a “stockholder” are to the record holder of the shares of Legacy common stock as to which appraisal rights are asserted. A person having a beneficial interest in shares of Legacy common stock held of record in the name of another person, such as a bank, broker or other nominee, must act promptly to cause the record holder to follow properly the steps summarized below and in a timely manner to perfect appraisal rights.

Under Section 262, where a proposed merger is to be submitted for approval at a meeting of stockholders, as in the case of Legacy’s special meeting, which is scheduled for June 20, 2011, the corporation, not less than 20 days prior to the meeting, must notify each of its stockholders entitled to appraisal rights that these appraisal rights are available and include in the notice a copy of Section 262. This document constitutes notice to the Legacy stockholders of the availability of appraisal rights, and the applicable statutory provisions of the Delaware General Corporation Law are attached to this document as Appendix D.

Any Legacy stockholder wishing to exercise the right to demand appraisal under Section 262 of the Delaware General Corporation Law must satisfy each of the following conditions:

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Only a stockholder of record of shares of Legacy common stock is entitled to assert appraisal rights for those shares registered in that holder’s name. A demand for appraisal should:

If the shares are owned of record by a person in a fiduciary capacity, such as a trustee, guardian or custodian, the demand should be executed in that capacity. If the shares are owned of record by more than one person as in a joint tenancy or tenancy in common, the demand should be executed by or on behalf of all owners. An authorized agent, including an agent for two or more joint owners, may execute a demand for appraisal on behalf of a stockholder; however, the agent must identify the record owner or owners and expressly disclose the fact that, in executing the demand, the agent is acting as agent for such owner or owners. A record holder such as a bank or broker who holds shares as nominee for several beneficial owners may exercise appraisal rights with respect to the shares held for one or more beneficial owners while not exercising these rights with respect to the shares held for one or more other beneficial owners. In this case, the written demand should set forth the number of shares as to which appraisal is sought, and where no number of shares is expressly mentioned the demand will be presumed to cover all shares held in the name of the record owner.

Stockholders who hold their shares in brokerage accounts or other nominee forms and who wish to exercise appraisal rights are urged to consult with their nominees to determine appropriate procedures for the making of a demand for appraisal by such nominee.

A stockholder who elects to exercise appraisal rights pursuant to Section 262 should mail or deliver a written demand to:

Legacy Bancorp, Inc.
99 North Street
P.O. Box 1148
Pittsfield, Massachusetts 01202
Attention: Kimberly A. Mathews, Corporate Secretary
and General Counsel

Within ten days after the completion of the Merger, Berkshire must send a notice as to the completion of the Merger to each of Legacy’s former stockholders who has made a written demand for appraisal in accordance with Section 262 and who has not voted in favor of or consented to adoption of the Merger Agreement. Within 120 days after the completion of the Merger, but not after that date, either Berkshire or any stockholder who has complied with the requirements of Section 262 may file a petition in the Delaware Court of Chancery demanding a determination of the value of the shares of common stock held by all stockholders demanding appraisal of their shares. Berkshire is under no obligation to, and has no present intent to file a petition for appraisal, and stockholders seeking to exercise appraisal rights should not assume that Berkshire Hills will file a petition or that it will initiate any negotiations with respect to the fair value of the shares. Accordingly, stockholders who desire to have their shares appraised should initiate any petitions necessary for the perfection of their appraisal rights within the time periods and in the manner prescribed in Section 262. Since Berkshire Hills has no obligation to file a petition, the failure of affected stockholders to do so within the period specified could nullify any previous written demand for appraisal. Under the Merger Agreement, Legacy has agreed to give Berkshire Hills prompt notice of any demands for appraisal it receives. Berkshire Hills has the right to participate in all negotiations and proceedings with respect to demands for appraisal. Legacy will not, except with the prior written consent of Berkshire Hills, make any payment with respect to any demands for appraisal, offer to settle, or settle, any demands.

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Within 120 days after the completion of the Merger, any stockholder that complies with the provisions of Section 262 to that point in time will be entitled to receive from Berkshire Hills, upon written request, a statement setting forth the aggregate number of shares not voted in favor of the Merger Agreement and with respect to which Legacy received demands for appraisal and the aggregate number of holders of those shares. Berkshire Hills must mail this statement to the stockholder by the later of ten days after receipt of the request or ten days after expiration of the period for delivery of demands for appraisals under Section 262.

A stockholder who timely files a petition for appraisal with the Delaware Court of Chancery must serve a copy upon Berkshire Hills. Berkshire Hills must, within 20 days of receipt of the petition, file with the Delaware Register in Chancery a duly verified list containing the names and addresses of all stockholders who have demanded appraisal of their shares and who have not reached agreements with it as to the value of their shares. After notice to stockholders as may be ordered by the Delaware Court of Chancery, the Delaware Court of Chancery is empowered to conduct a hearing on the petition to determine which stockholders are entitled to appraisal rights. The Delaware Court of Chancery may require stockholders who have demanded an appraisal for their shares and who hold stock represented by certificates to submit their certificates to the Register in Chancery for notation on the certificates of the pendency of the appraisal proceedings, and if any stockholder fails to comply with the requirement, the Delaware Court of Chancery may dismiss the proceedings as to that stockholder. After determining what stockholders are entitled to an appraisal, the Delaware Court of Chancery will appraise the “fair value” of their shares. This value will exclude any element of value arising from the accomplishment or expectation of the Merger, but will include a fair rate of interest, if any, to be paid upon the amount determined to be the fair value. The costs of the action may be determined by the Delaware Court of Chancery and taxed upon the parties as the Delaware Court of Chancery deems equitable. Upon application of a stockholder, the Delaware Court of Chancery may also order that all or a portion of the expenses incurred by any stockholder in connection with the appraisal proceeding be charged pro rata against the value of all of the shares entitled to appraisal. These expenses may include, without limitation, reasonable attorneys’ fees and the fees and expenses of experts. Stockholders considering seeking appraisal should be aware that the fair value of their shares as determined under Section 262 could be more than, the same as, or less than the Merger consideration they would be entitled to receive pursuant to the Merger Agreement if they did not seek appraisal of their shares. Stockholders should also be aware that investment banking opinions as to fairness from a financial point of view are not necessarily opinions as to fair value under Section 262.

In determining fair value and, if applicable, a fair rate of interest, the Delaware Court of Chancery is to take into account all relevant factors. In Weinberger v. UOP, Inc., the Delaware Supreme Court discussed the factors that could be considered in determining fair value in an appraisal proceeding, stating that “proof of value by any techniques or methods which are generally considered acceptable in the financial community and otherwise admissible in court” should be considered, and that “fair price obviously requires consideration of all relevant factors involving the value of a company.”

Section 262 provides that fair value is to be “exclusive of any element of value arising from the accomplishment or expectation of the Merger.” In Cede & Co. v. Technicolor, Inc., the Delaware Supreme Court stated that such exclusion is a “narrow exclusion [that] does not encompass known elements of value,” but which rather applies only to the speculative elements of value arising from such accomplishment or expectation. In Weinberger, the Delaware Supreme Court construed Section 262 to mean that “elements of future value, including the nature of the enterprise, which are known or susceptible of proof as of the date of the Merger and not the product of speculation, may be considered.” Any stockholder who has duly demanded an appraisal in compliance with Section 262 will not, after the completion of the Merger, be entitled to vote the shares subject to that demand for any purpose or be entitled to the payment of dividends or other distributions on those shares. However, stockholders will be entitled to dividends or other distributions payable to holders of record of shares as of a record date prior to the completion of the Merger.

Any stockholder may withdraw its demand for appraisal and accept the Merger consideration by delivering to Berkshire Hills, within 60 days of the effective date of the Merger, a written withdrawal of the stockholder’s demands for appraisal. Any attempt to withdraw made more than 60 days after the effective date of the Merger will require written approval of Berkshire Hills. Moreover, no appraisal proceeding before the Delaware Court of Chancery as to any stockholder shall be dismissed without the approval of the Delaware

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Court of Chancery, and such approval may be conditioned upon any terms the Delaware Court of Chancery deems just. If Berkshire Hills does not approve a stockholder’s request to withdraw a demand for appraisal when the approval is required or if the Delaware Court of Chancery does not approve the dismissal of an appraisal proceeding, the stockholder would be entitled to receive only the appraised value determined in any such appraisal proceeding. This value could be higher or lower than, or the same as, the value of the Merger consideration.

Failure to follow the steps required by Section 262 of the Delaware General Corporation Law for perfecting appraisal rights may result in the loss of appraisal rights, in which event you will be entitled to receive the consideration with respect to your dissenting shares in accordance with the Merger Agreement. In view of the complexity of the provisions of Section 262 of the Delaware General Corporation Law, if you are a Legacy stockholder and are considering exercising your appraisal rights under the Delaware General Corporation Law, you should consult your own legal advisor.

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DESCRIPTION OF THE MERGER

The following summary of the Merger Agreement is qualified by reference to the complete text of the Merger Agreement. A copy of the Merger Agreement is attached as Appendix A to this Joint Proxy Statement/Prospectus and is incorporated by reference into this Joint Proxy Statement/Prospectus. You should read the Merger Agreement completely and carefully as it, rather than this description, is the legal document that governs the Merger.

General

The Merger Agreement provides for the merger of Legacy with and into Berkshire Hills, with Berkshire Hills as the surviving entity. Following the merger of Legacy with and into Berkshire Hills, Berkshire Hills intends to merge Legacy Banks with and into Berkshire Bank, but retains the right to hold Legacy Banks as a separate subsidiary. In connection with a merger of Legacy Banks with and into Berkshire Bank, Berkshire Hills may, subject to regulatory approval, include the “Legacy” name in the name of Berkshire Bank’s branch offices in Berkshire County, Massachusetts and may continue to do so for up to two years from the completion of the Merger or until such time as Berkshire Bank rebrands its banking offices in Berkshire County, Massachusetts. Berkshire Hills will designate the headquarters of Berkshire Hills and Berkshire Bank as 99 North Street, Pittsfield, Massachusetts.

Background of the Merger