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Filed Pursuant to Rule 424(b)(3)

Registration No. 333-182517

MERGER PROPOSED — YOUR VOTE IS VERY IMPORTANT

The boards of directors of Berkshire Hills Bancorp, Inc. (“BHLB”) and Beacon Federal Bancorp, Inc. (“Beacon”) have agreed to a merger of our companies.  If the merger is completed, each share of Beacon common stock, par value $0.01 per share, will be converted into the right to receive either 0.92 of a share of BHLB common stock, par value $0.01 per share, or $20.50 in cash, or a combination of BHLB common stock and cash, subject to 50% of Beacon’s common stock being exchanged for BHLB’s common stock and 50% of Beacon’s common stock being exchanged for cash.  BHLB’s shareholders will continue to own their existing shares.  After completion of the merger, we expect that current BHLB shareholders will own approximately 89% of the combined company and Beacon shareholders will own approximately 11% of the combined company based on the shares outstanding as of May 31, 2012.  BHLB common stock is listed on the NASDAQ Global Select Market under the symbol “BHLB.”  Beacon common stock is listed on the NASDAQ Global Market under the symbol “BFED.” On August 6, 2012, the closing price of BHLB common stock was $22.51 and the closing price of Beacon common stock was $20.25.  BHLB is offering approximately 2,852,000 shares of its common stock to Beacon shareholders.

We expect the merger to generally be tax-free for federal income tax purposes to holders of Beacon common stock to the extent they receive BHLB common stock.  Any cash consideration received will be taxable to Beacon shareholders.

We cannot complete the merger unless we obtain the necessary regulatory approvals and unless the shareholders of Beacon approve the merger agreement.  Beacon is asking its shareholders to consider and vote on this merger proposal at its special meeting of shareholders in addition to considering and voting on a proposal to approve, by a non-binding, advisory vote, certain compensation arrangements for Beacon’s named executive officers in connection with the merger and a proposal to adjourn the special meeting, if necessary, in order to solicit additional proxies to vote in favor of the merger agreement. Whether or not you plan to attend the Beacon shareholder’s meeting, please take the time to vote by completing and mailing the enclosed proxy card in accordance with the instructions.  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” the merger and the transactions contemplated by the merger agreement, the proposal regarding certain merger-related executive compensation arrangements and an adjournment of the special meeting, if necessary.  If you do not return your proxy card, or if you do not instruct your broker how to vote any shares held for you in “street name,” the effect will be a vote against the merger agreement.  Beacon shareholders do not have dissenters’ rights under its articles of incorporation.

Beacon’s board of directors has unanimously determined that the merger is advisable, fair to, and in the best interests of Beacon and its shareholders and recommends that you vote “FOR” the approval of the merger agreement, the proposal regarding certain merger-related executive compensation arrangements and the adjournment of the special meeting, if necessary, in order to solicit additional proxies to vote in favor of the merger agreement.

The place, date and time of the Beacon shareholders’ meeting is as follows:

Beacon Federal Bancorp, Inc.

6611 Manlius Center Road

East Syracuse, New York 13057

September 20, 2012, 10:30 a.m.

This document contains a more complete description of the Beacon shareholders’ meeting and the terms of the merger.  We urge you to review this entire document carefully, including the “Risk Factors” beginning on page 11 for a discussion of the risks related to the proposed merger.  You may also obtain information about BHLB and Beacon from documents both companies have filed with the Securities and Exchange Commission.

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Neither the Securities and Exchange Commission nor any state securities commission has approved or disapproved of the merger or the securities to be issued under this proxy statement/prospectus or determined if this proxy statement/prospectus is accurate or adequate.  Any representation to the contrary is a criminal offense.

The securities we are offering through this document are not savings or deposit accounts or other obligations of any bank or non-bank subsidiary of either of our companies, and they are not insured by the Federal Deposit Insurance Corporation or any other governmental agency.

Proxy Statement/Prospectus dated August 6, 2012

and first mailed to shareholders on or about August 16, 2012

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This document incorporates important business and financial information about BHLB and Beacon from documents filed with the Securities and Exchange Commission that have not been included in or delivered with this document. You may read and copy these documents at the Securities and Exchange Commission’s public reference facilities. Please call the SEC at 1-800-SEC-0330 for information about these facilities. This information is also available at the Internet site the SEC maintains at http://www.sec.gov.  See “Where You Can Find More Information” on page 77.

You also may request copies of these documents from BHLB and Beacon.  BHLB and Beacon will provide you with copies of these documents, without charge, upon written or oral request to:

Berkshire Hills Bancorp, Inc.

24 North Street

Pittsfield, Massachusetts 01201

Attention: Investor Relations Department

Telephone: (413) 236-3239

Beacon Federal Bancorp, Inc.

6611 Manlius Center Road

East Syracuse, New York 13057

Attn:  Darren T. Crossett

Telephone:  (315) 433-0111

If you are a Beacon shareholder and would like to request documents from BHLB or Beacon, please do so by September 13, 2012 to receive them before the Beacon shareholders’ meeting.

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BEACON FEDERAL BANCORP, INC.
6611 Manlius Center Road
East Syracuse, New York 13057

Notice of Special Meeting of Shareholders
to be held September 20, 2012

A special meeting of shareholders of Beacon Federal Bancorp, Inc. will be held at 10:30 a.m., local time, on September 20, 2012 at 6611 Manlius Center Road, East Syracuse, New York 13057.  Any adjournments or postponements of the special meeting will be held at the same location.

At the special meeting, you will be asked to:

1.                                    Consider and vote upon a proposal to approve the Agreement and Plan of Merger, dated as of May 31, 2012, by and between Berkshire Hills Bancorp, Inc. and Beacon Federal Bancorp, Inc.  A copy of the merger agreement is included as Annex A to the accompanying proxy statement/prospectus;

2.                                    Consider and vote upon a proposal to approve, by non-binding, advisory vote, certain compensation arrangements for Beacon Federal Bancorp, Inc.’s named executive officers in connection with the merger;

3.                                    Consider and vote upon a 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; and

4.                                    Transact such other business as may be properly presented at the special meeting and any adjournments or postponements of the special meeting.

The enclosed proxy statement/prospectus describes the merger agreement and the proposed merger in detail.  We urge you to read these materials carefully.  The enclosed proxy statement/prospectus forms a part of this notice.

The board of directors of Beacon Federal Bancorp, Inc. unanimously recommends that Beacon Federal Bancorp, Inc. shareholders vote “FOR” the proposal to approve the merger agreement, “FOR” the proposal to approve, by non-binding advisory vote, certain compensation arrangements for Beacon Federal Bancorp, Inc.’s named executive officers in connection with the merger and “FOR” the proposal to adjourn the special meeting, if necessary, to solicit additional proxies to vote in favor of the merger agreement.

The board of directors of Beacon Federal Bancorp, Inc. has fixed the close of business on August 3, 2012 as the record date for determining the shareholders entitled to notice of, and to vote at, the special meeting and any adjournments or postponements of the special meeting.

Your vote is very important.  Your proxy is being solicited by Beacon Federal Bancorp, Inc. board of directors. The proposal to approve the merger agreement must be approved by the affirmative vote of holders of at least a majority of the outstanding shares of Beacon Federal Bancorp, Inc. common stock entitled to vote in order for the proposed merger to be consummated. Whether or not you plan to attend the special meeting in person, we urge you to complete and mail the enclosed proxy card, in the accompanying envelope, which requires no postage if mailed in the United States. You may revoke your proxy at any time before the special meeting. If you attend the special meeting and vote in person, your proxy vote will not be used.

Beacon Federal Bancorp, Inc. shareholders do not have dissenters’ rights under Beacon’s articles of incorporation.  See “Questions and Answers About the Merger and the Special Meeting” on page 1 and “No Dissenters’ Rights” on page 36.

East Syracuse, New York

August 16, 2012

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QUESTIONS AND ANSWERS ABOUT THE MERGER AND THE SPECIAL MEETING

Q:               What am I being asked to vote on? What is the proposed transaction?

A:               You are being asked to vote on the approval of a merger agreement that provides for the acquisition of Beacon Federal Bancorp, Inc. (“Beacon”) by Berkshire Hills Bancorp, Inc. (“BHLB”) and the merger of Beacon’s banking subsidiary Beacon Federal into BHLB’s banking subsidiary, Berkshire Bank.  A copy of the merger agreement is provided as Annex A to this document.  The Beacon board of directors has determined that the proposed merger is advisable and in the best interests of its shareholders, has unanimously approved the merger agreement and recommends that its shareholders vote “FOR” the approval of the merger agreement.

Q:               What will Beacon shareholders be entitled to receive in the merger?

A:               Under the merger agreement, at the election of each Beacon shareholder, each share of Beacon common stock will be exchanged for either 0.92 of a share of BHLB common stock (the “Exchange Ratio”) or $20.50 in cash.  Each Beacon shareholder may elect either of these options or each Beacon shareholder may elect to exchange some of his or her Beacon shares for cash and some of his or her Beacon shares for BHLB shares.

Elections will be limited by, among other things, a requirement that 50% of the total number of outstanding shares of Beacon common stock be exchanged for BHLB common stock.  Therefore, the form of consideration received will depend in part on the elections of other Beacon shareholders.

BHLB will not issue fractional shares in the merger.  Instead, each Beacon shareholder will receive a cash payment, without interest, for the value of any fraction of a share of BHLB common stock that such shareholder would otherwise be entitled to receive.  See “Description of the Merger—Consideration to be Received in the Merger” on page 47 and “Description of Berkshire Hills Bancorp, Inc. Capital Stock” on page 64.

Q:               What dividends will be paid after the merger?

A:               BHLB currently pays a quarterly dividend of $0.17 per share.  Although BHLB has paid quarterly dividends on its common stock without interruption since November 2000, there is no guarantee that BHLB will continue to pay dividends on its common stock.  All dividends on BHLB common stock are declared at the discretion of the BHLB board of directors.

Q:               How does a Beacon shareholder elect to receive cash, stock or a combination of both for his or her Beacon stock?

A:               For each registered Beacon shareholder, a form for making an election will be provided under separate cover.  For the election to be effective, the properly completed election form, along with the Beacon stock certificates or an appropriate guarantee of delivery, must be sent to and received by Registrar and Transfer Company, the exchange agent, on or before 5:00 p.m., Eastern time, on the date specified on the election form.  The election form should not be sent together with your proxy card.  Instead, use the separate envelope specifically provided for the election form and your stock certificates.  If a timely and properly completed election is not made, you will be allocated BHLB common stock and/or cash depending on your election and the elections made by other shareholders.

If the shares you own are held in “street name” by a bank or brokerage firm, your bank or brokerage firm, as the record holder of your shares, is required to provide you with an election form.  In order to make an election for your shares held in “street name,” you will need to follow the instructions your bank or brokerage firm provides to you.

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Q:               How does a Beacon shareholder exchange his or her stock certificates?

A:               If an election is made, the Beacon stock certificates or an appropriate guarantee of delivery must be returned with the election form.  Shortly after the merger, the exchange agent will allocate cash and BHLB common stock among Beacon shareholders, consistent with their elections and the allocation and proration procedures in the merger agreement.  If a Beacon shareholder does not submit an election form, BHLB’s exchange agent will send instructions on how and where to surrender the Beacon stock certificates after the merger is completed.  Please do not send Beacon stock certificates with the proxy card.

Q:               What are the tax consequences of the merger to Beacon shareholders?

A:               The tax consequence of the merger to Beacon shareholders will depend on whether only cash, only BHLB common stock, or a combination of cash and BHLB common stock is received in exchange for shares of Beacon common stock.  If shares are exchanged solely for BHLB common stock, no gain or loss should be recognized except with respect to the cash received instead of any fractional share of BHLB common stock.  If shares are exchanged solely for cash, a gain or loss should be recognized on the exchange.  If shares were exchanged for a combination of BHLB common stock and cash, a gain should be recognized equal to the lesser of the cash received or the gain realized in the merger (that is, the fair market value of the BHLB common stock received, plus the cash received, and minus the Beacon shareholder’s basis in the shareholder’s Beacon common stock).  No loss should be recognized.  See “Description of the Merger—Material Tax Consequences of the Merger” on page 50.

Because the allocations of cash and BHLB common stock received will depend on the elections of other Beacon shareholders, the actual tax consequences of the merger will not be known until the allocations are completed.

Q:               Are Beacon shareholders entitled to dissenters’ rights?

A:               No.  As permitted by Maryland law, the Beacon articles of incorporation provide that the holders of Beacon common stock are not entitled to exercise the rights of an objecting shareholder.

Q:               Why do Beacon and BHLB want to merge?

A:               Beacon believes that the proposed merger will provide Beacon shareholders with substantial benefits, and BHLB believes that the merger will further its strategic growth plans.  As a larger company, BHLB can provide the capital and resources that Beacon needs to compete more effectively and to offer a broader array of products and services to better serve its banking customers. To review the reasons for the merger in more detail, see “Description of the Merger—Beacon’s Reasons for the Merger” on page 36.

Q:               What vote is required to approve the merger agreement?

A:               Holders of at least a majority of the outstanding shares of Beacon common stock entitled to vote must vote in favor of the proposal to approve the merger agreement.

Q:                Why are Beacon shareholders being asked to approve, on a non-binding advisory basis, certain merger-related executive compensation arrangements?

A:                 The SEC has recently adopted new rules that require Beacon to seek a non-binding advisory vote with respect to certain payments that may be made to Beacon’s named executive officers in connection with the merger.

Q:                What will happen if Beacon shareholders do not approve certain merger-related executive compensation arrangements at the special meeting?

A:                 Approval of merger-related executive compensation arrangements, payable under existing agreements, that certain Beacon named executive officers may receive in connection with the merger is not a condition to completion of the merger. The vote with respect to the merger-related executive compensation arrangements is

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an advisory vote and will not be binding on Beacon. Therefore, if the merger agreement is approved by Beacon’s shareholders the merger-related executive compensation arrangements may still be paid to the Beacon named executive officers if and to the extent required or allowed under applicable law.

Q:               When and where is the Beacon special meeting?

A:               The special meeting of Beacon shareholders is scheduled to take place at 6611 Manlius Center Road, East Syracuse, New York 13057 at 10:30 a.m., local time, on September 20, 2012.

Q:                Who is entitled to vote at the Beacon special meeting?

A:                Holders of shares of Beacon common stock at the close of business on August 3, 2012, which is the record date, are entitled to vote on the proposal to adopt the merger agreement and the other proposals in this proxy statement/prospectus. As of the record date, 6,203,900 shares of Beacon common stock were outstanding and entitled to vote.

Q:               If I plan to attend the Beacon special meeting in person, should I still return my proxy?

A:               Yes. Whether or not you plan to attend the Beacon special meeting, you should complete and return the enclosed proxy card.  The failure of a Beacon shareholder to vote in person or by proxy will have the same effect as a vote “AGAINST” the merger agreement.

Q:               What do I need to do now to vote my shares of Beacon common stock?

A:               After you have carefully read and considered the information contained in this proxy statement/prospectus, please complete, sign, date and mail your proxy card in the enclosed return envelope as soon as possible. This will enable your shares to be represented at the special meeting. You may also vote in person at the special meeting.  If you do not return a properly executed proxy card and do not vote at the special meeting, this will have the same effect as a vote against the merger agreement. If you sign, date and send in your proxy card, but you do not indicate how you want to vote, your proxy will be voted in favor of adoption of the merger agreement, the proposal regarding certain merger-related executive compensation arrangements and an adjournment of the special meeting, if necessary. You may change your vote or revoke your proxy before the special meeting by filing with the Corporate Secretary of Beacon a duly executed revocation of proxy, submitting a new proxy card with a later date, or voting in person at the special meeting.

Q:               If my shares are held in “street name” by my broker, will my broker automatically vote my shares for me?

A:               No.  Your broker will not be able to vote your shares of Beacon common stock on the proposal to adopt the merger agreement unless you provide instructions on how to vote.  Please instruct your broker how to vote your shares, following the directions that your broker provides.  If you do not provide instructions to your broker on the proposal to approve the merger agreement, the proposal regarding certain merger-related executive compensation arrangements or the proposal regarding adjournment, your shares will not be voted, and this will have the effect of voting against the merger agreement, the proposal regarding certain merger-related executive compensation arrangements and the proposal regarding adjournment.  Please check the voting form used by your broker to see if it offers telephone or Internet voting.

Q:           When is the merger expected to be completed?

A:               We will try to complete the merger as soon as possible.  Before that happens, the merger agreement must be approved by Beacon shareholders and we must obtain the necessary regulatory approvals. Assuming holders of at least a majority of the outstanding shares of Beacon common stock vote in favor of the merger agreement and we obtain the other necessary approvals, we expect to complete the merger in the fourth calendar quarter of 2012.

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Q:               Is completion of the merger subject to any conditions besides shareholder approval?

A:               Yes. The transaction must receive the required regulatory approvals, and there are other customary closing conditions that must be satisfied.  To review the conditions of the merger in more detail, see “Description of the Merger—Conditions to Completing the Merger” on page 57.

Q:               Who can answer my other questions?

A:               If you have more questions about the merger, or how to submit your proxy or if you need additional copies of this proxy statement/prospectus or the enclosed proxy form, Beacon shareholders should contact its proxy solicitor:

Phoenix Advisory Partners, LLC

110 Wall Street, 27th Floor

New York, New York 10005

(877) 478-5038

Banks and brokers should call:

(212) 493-3910

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SUMMARY

This summary highlights selected information in this 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 proxy statement/prospectus.

The Companies

Berkshire Hills Bancorp, Inc.
24 North Street

Pittsfield, Massachusetts 01201

(413) 443-5601

Berkshire Hills Bancorp, Inc., a Delaware corporation, is a savings and loan holding company headquartered in Pittsfield, Massachusetts that was incorporated and commenced operations in 2000.  BHLB’s common stock is listed on The NASDAQ Global Select Market under the symbol “BHLB.”  BHLB conducts its operations primarily through Berkshire Bank, a Massachusetts chartered savings bank with 68 full service branch offices in Massachusetts, Connecticut, New York and Vermont.  Berkshire Bank, America’s Most Exciting Bank(SM) is one of Massachusetts’ oldest and largest independent banks and is the largest banking institution based in Western Massachusetts.  Berkshire Bank provides personal and business banking, insurance, and wealth management services.  Berkshire Bank provides 100% deposit insurance protection for all deposit accounts, regardless of amount, based on a combination of FDIC insurance and the Depositors Insurance Fund (“DIF”).  BHLB is also the holding company for Berkshire Insurance Group, an insurance agency in Western Massachusetts.  At March 31, 2012, BHLB had total assets of $4.0 billion, total deposits of $3.2 billion and total shareholders’ equity of $556.8 million.  On April 20, 2012, BHLB completed its acquisition of The Connecticut Bank and Trust Company, a $280.0 million bank with eight banking offices in the greater Hartford, Connecticut area.

Beacon Federal Bancorp, Inc.

6611 Manlius Center Road

East Syracuse, New York 13057

(315) 336-7300

Beacon Federal Bancorp, Inc., a Maryland corporation, is the holding company for Beacon Federal, a federally chartered savings association that converted to a stock savings association in connection with its initial public offering of common stock in October 2007.  Beacon Federal offers banking and related financial services to both individual and commercial customers.  Beacon Federal is headquartered in East Syracuse, New York and operates from six other full-service offices in East Syracuse, Marcy and Rome, New York, Smartt and Smyrna, Tennessee, and Chelmsford, Massachusetts.

At March 31, 2012, Beacon had total assets of $1.0 billion, total deposits of $677.3 million and total shareholders’ equity at $113.9 million.

Beacon’s executive offices are located at 6611 Manlius Center Road, East Syracuse, New York 13057.  Its telephone number at this address is (315) 433-0111.

Special Meeting of Beacon Shareholders; Required Vote (page 34)

A special meeting of Beacon shareholders is scheduled to be held at 6611 Manlius Center Road, East Syracuse, New York 13057 at 10:30 a.m., local time, on September 20, 2012.  At the special meeting, you will be asked to vote on a proposal to approve the merger agreement between Beacon and BHLB and a proposal regarding certain merger-related executive compensation arrangements.  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.

Only Beacon shareholders of record as of the close of business on August 3, 2012 are entitled to notice of, and to vote at, the Beacon special meeting and any adjournments or postponements of the meeting.

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Approval of the merger agreement requires the affirmative vote of holders of at least a majority of the outstanding shares of Beacon common stock entitled to vote.  Approval of the non-binding proposal regarding certain merger-related executive compensation arrangements requires the affirmative vote of a majority of the votes cast on the matter.  As of the record date, there were 6,203,900 shares of Beacon common stock outstanding.  The directors and executive officers of Beacon, as a group, beneficially owned 440,512 shares of Beacon common stock (not including shares that may be acquired upon the exercise of stock options), representing 7.1% of the outstanding shares of Beacon common stock as of the record date and have agreed to vote their shares in favor of the merger at the special meeting.

The Merger and the Merger Agreement (page 36)

BHLB’s acquisition of Beacon is governed by a merger agreement.  The merger agreement provides that, if all of the conditions are satisfied or waived, Beacon will be merged with and into BHLB, with BHLB as the surviving entity.  Additionally, Beacon Federal will be merged with and into Berkshire Bank, with Berkshire Bank as the surviving entity.  We encourage you to read the merger agreement, which is included as Annex A to this proxy statement/prospectus.

What Beacon Shareholders Will Receive in the Consideration to be Received in the Merger (page 47)

Under the merger agreement, at your election, each share of Beacon common stock you own will be exchanged for either 0.92 of a share of BHLB common stock, $20.50 in cash, or a combination of cash and BHLB common stock, subject to 50% of the aggregate merger consideration being exchanged for BHLB common stock.

Comparative Market Prices (page 33)

The following table shows the closing price per share of BHLB common stock and the equivalent price per share of Beacon common stock, giving effect to the merger, on May 30, 2012, which is the last day on which shares of BHLB common stock traded preceding the public announcement of the proposed merger, and on August 6, 2012, the most recent practicable date prior to the mailing of this proxy statement/prospectus.  The equivalent price per share of Beacon common stock was computed by multiplying the price of a share of BHLB common stock by the 0.92 exchange ratio and does not include the value of any cash received by a Beacon shareholder.  Shareholders who elect to receive cash consideration in the merger will receive $20.50 for each share of Beacon common stock that they hold, subject to the allocation and proration provisions of the merger agreement.  See “Description of the Merger—Consideration to be Received in the Merger” on page 47.

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Recommendation of Beacon’s Board of Directors (page 36)

The Beacon board of directors has unanimously approved the merger agreement and the proposed merger. The Beacon board believes that the merger agreement, including the merger contemplated by the merger agreement, is fair to, and in the best interests of, Beacon and its shareholders, and therefore unanimously recommends that Beacon shareholders vote “FOR” the proposal to approve the merger agreement.  In reaching this decision, Beacon’s board of directors considered a variety of factors, which are described in the section captioned “Description of the Merger—Beacon’s Reasons for the Merger” beginning on page 39.

The Beacon board of directors unanimously recommends that Beacon shareholders vote “FOR” approval of the non-binding proposal regarding certain merger-related executive compensation arrangements and “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 Beacon’s Financial Advisor (page 40)

In deciding to approve the merger, one of the factors considered by Beacon’s board of directors was the opinion of Keefe, Bruyette & Woods, Inc., (“KBW”) which served as financial advisor to Beacon’s board of directors.  KBW delivered its written opinion on May 31, 2012, that the merger consideration is fair to the holders of Beacon common stock from a financial point of view.  The full text of this opinion is included as Annex B to the 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.  Beacon has agreed to pay KBW a fee equal to $200,000 plus 1.00% of the aggregate consideration offered in exchange for the outstanding shares of common stock or assets of Beacon in the merger.  KBW has received a fee of $200,000 for the rendering of its fairness opinion, which fee shall be credited against the fee referenced above if the merger is completed.

Regulatory Matters Relating to the Merger (page 53)

Under the terms of the merger agreement, the merger cannot be completed unless it is first approved by the Massachusetts Division of Banks, the Massachusetts Board of Bank Incorporation and the Federal Deposit Insurance Corporation.  BHLB filed the required applications in July, 2012.  As of the date of this document, BHLB has not received any approvals from those regulators.  While BHLB does not know of any reason why it would not be able to obtain approval in a timely manner, BHLB cannot be certain when or if it will receive regulatory approval.

Conditions to Completing the Merger (page 57)

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

·                  approval of the merger agreement at the special meeting by at least a majority of the outstanding shares of Beacon common stock entitled to vote;

·                  approval of the transaction by the appropriate regulatory authorities;

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·                  receipt by each party of opinions from their respective legal counsel to the effect that the merger will be treated for federal income tax purposes as a reorganization within the meaning of Section 368(a) of the Internal Revenue Code;

·                  the accuracy of representations and warranties made on the date of the merger agreement;

·                  no material adverse effect on either party has occurred; and

·                  such other conditions customary to merger transactions.

Terminating the Merger Agreement (page 63)

The merger agreement may be terminated by mutual consent of BHLB and Beacon at any time prior to the completion of the merger.  Additionally, subject to conditions and circumstances described in the merger agreement, either BHLB or Beacon may terminate the merger agreement if, among other things, any of the following occur:

·                  the merger has not been consummated by May 31, 2013;

·                  Beacon shareholders do not approve the merger agreement at the Beacon special meeting;

·                  a required regulatory approval is denied or a governmental authority enjoins or prohibits the merger; or

·                  there is a breach by the other party of any representation, warranty, covenant or agreement contained in the merger agreement, which cannot be cured, or has not been cured within 30 days after the giving of written notice to such party of such breach.

BHLB may also terminate the merger agreement if Beacon has received a Superior Proposal and Beacon has entered into an acquisition agreement with respect to such Superior Proposal or if the board of directors of Beacon does not recommend approval of the merger in the proxy statement/prospectus or withdraws or revises its recommendation in a manner adverse to BHLB.

Additionally, Beacon may terminate the merger agreement if, at any time during the five-day period commencing on the first date on which all bank regulatory approvals (and waivers, if applicable) necessary for consummation of the merger have been received (disregarding any waiting period) (the “Determination Date”), such termination to be effective if both of the following conditions are satisfied:

·                  the average of the daily closing price of BHLB common stock for the twenty consecutive trading days preceding the Determination Date (“BHLB Market Value”) is less than $17.82; and

·                  the number obtained by dividing the BHLB Market Value by $22.28 on the Determination Date is less than the number obtained by dividing (i) the weighted average of the daily closing prices for the ten consecutive trading days immediately preceding the Determination Date of the bank index included in the merger agreement (the “Final Index Price”) by (ii) the weighted average closing price of the bank index included in the merger agreement on the last trading date immediately preceding the public announcement of the entry into the merger agreement (the “Initial Index Price”), minus 0.20.

If Beacon elects to terminate the merger agreement under this provision, BHLB may elect to adjust the exchange ratio to an amount that would not make termination under this event possible, in which case no termination would occur.

Termination Fee (page 64)

Under certain circumstances described in the merger agreement, BHLB may demand from Beacon a $5.28 million termination fee in connection with the termination of the merger agreement.  See “Description of the Merger—Termination Fee” on page 64 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 54)

In considering the recommendation of the board of directors of Beacon to adopt the merger agreement, you should be aware that officers and directors of Beacon have employment and other compensation agreements or economic interests that give them interests in the merger that are somewhat different from, or in addition to, their

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interests as Beacon shareholders. These interests and agreements provide for cash severance payments in the aggregate amount of up to approximately $3.3 million.  Some of the interests of the officers and directors include:

·             Employment agreements for Ross J. Prossner, President and Chief Executive Officer of Beacon, Darren T. Crossett, Senior Vice President of Beacon, J. David Hammond, Senior Vice President and Chief Lending Officer of Beacon, and one other officer that provide for cash severance payments upon the occurrence of a change in control;

·             Change in control agreements with six officers of Beacon that provide for cash severance payments and continued health insurance in connection with a termination of employment without cause or for good reason following a change in control;

·             Supplemental Executive Retirement Plan for Ross J. Prossner that provides for a fully vested benefit in connection with a termination of employment without cause or for good reason.  The plan provides for the same benefit absent a change in control;

·             Interests under an Excess Benefit Plan for Messrs. Prossner, Crossett and Hammond, which will be terminated in connection with a change in control, with the benefits paid to the participants in a lump sum;

·             Beacon has made awards of stock options and/or restricted stock to certain officers under its equity incentive plan.  As a result of the merger, each stock option will be assumed by BHLB and each share of such restricted stock will be exchanged for shares of BHLB common stock subject to the same restrictions, unless the Beacon equity incentive plan provides for acceleration of vesting or lapse of restrictions as a result of the merger.  The number of stock options, restricted stock awards and the exercise price of the stock options will be adjusted for the Exchange Ratio.

·             One person who is a director of Beacon, as determined by BHLB and Berkshire Bank, shall be appointed and elected to the BHLB and Berkshire Bank boards of directors;

·             The board members of Beacon who do not join the boards of BHLB or Berkshire Bank shall be appointed to a currently existing advisory board of Berkshire Bank.  Each member of the advisory board shall receive compensation as set by the board of directors of Berkshire Bank from time to time.  Berkshire Bank shall consider the composition, compensation and need for the advisory board after the completion of a one-year term by the joining Beacon directors; and

·             Rights of Beacon officers and directors to continued indemnification coverage and continued coverage under directors’ and officers’ liability insurance policies.

Approval of the Non-Binding Proposal Regarding Certain Merger-Related Executive Compensation Arrangements Requires the Affirmative Vote of the Holders of a Majority of the Outstanding Shares of Beacon Common Stock Cast (Page 75)

Approval of the non-binding proposal regarding certain merger-related executive compensation arrangements requires the affirmative vote of a majority of the votes cast on the matter. Shareholders should note that the non-binding proposal regarding certain merger-related executive compensation arrangements is merely an advisory vote which will not be binding on Beacon, Beacon’s Board of Directors, or BHLB.  Further, the underlying plans and arrangements are contractual in nature and not, by their terms, subject to shareholder approval.  Accordingly, regardless of the outcome of the non-binding, advisory vote, if the merger is consummated, Beacon’s named executive officers will be eligible to receive the various payments and benefits in accordance with the terms and conditions applicable to those arrangements.

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Accounting Treatment of the Merger (page 49)

The merger will be accounted for in accordance with accounting standards for business combinations in accordance with U.S. generally accepted accounting principles.

Comparison of Rights of Shareholders (page 67)

When the merger is completed, Beacon shareholders who are to receive shares of BHLB will become BHLB shareholders and their rights will be governed by Delaware law and by BHLB’s certificate of incorporation and bylaws. See “Comparison of Rights of Shareholders” beginning on page 67 for a summary of the material differences between the respective rights of Beacon and BHLB shareholders.

No Dissenters’ Rights (page 36)

Beacon shareholders do not have dissenters’ rights under Maryland law since the Beacon articles of incorporation provide that the holders of Beacon common stock are not entitled to exercise the rights of an objecting stockholder.  See “No Dissenters’ Rights” on page 36.

Material Tax Consequences of the Merger (page 50)

The federal tax consequences of the merger to shareholders of Beacon will depend primarily on whether they exchange their Beacon common stock solely for BHLB common stock, solely for cash or for a combination of BHLB common stock and cash.  Beacon shareholders who exchange their shares solely for BHLB common stock should not recognize a gain or loss except with respect to the cash they receive instead of a fractional share BHLB common stock.  Beacon shareholders who exchange their shares solely for cash should recognize a gain or loss on the exchange.  Beacon shareholders who exchange their shares for a combination of BHLB common stock and cash should recognize a gain, but not any loss, on the exchange.  The actual federal income tax consequences to Beacon shareholders of electing to receive cash, BHLB common stock or a combination of cash and stock will not be ascertainable at the time Beacon shareholders make their election because it will not be known at that time how, or to what extent, the allocation and proration procedures will apply.

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

To review the tax consequences of the merger to Beacon shareholders in greater detail, please see the section “Description of the Merger—Material Tax Consequences of the Merger” beginning on page 50.

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RISK FACTORS

In addition to the other information contained in or incorporated by reference into this 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 proxy statement/prospectus titled “Caution About Forward-Looking Statements” beginning on page 14.

Beacon shareholders may receive a form of consideration different from what they elect.

The consideration to be received by Beacon shareholders in the merger is subject to the requirement that 50% of the shares of Beacon common stock be exchanged for BHLB common stock and the remaining 50% be exchanged for cash.  The merger agreement contains proration and allocation methods to achieve this desired result.  If you elect all cash and the available cash is oversubscribed, then you will receive a portion of the merger consideration in BHLB common stock.  If you elect all stock and the available stock is oversubscribed, then you will receive a portion of the merger consideration in cash.

The price of BHLB common stock might decrease after the merger.

Following the merger, many holders of Beacon common stock will become shareholders of BHLB.  BHLB common stock could decline in value after the merger. For example, during the twelve-month period ending on August 6, 2012 (the most recent practicable date before the printing of this proxy statement/prospectus), the price of BHLB common stock varied from a low of $17.11 to a high of $24.49 and ended that period at $22.51.  The market value of BHLB common stock fluctuates based upon general market economic conditions, BHLB’s business and prospects and other factors.

BHLB may be unable to successfully integrate Beacon’s operations and retain Beacon’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:

·                  integrating personnel with diverse business backgrounds;

·                  combining different corporate cultures; and

·                  retaining key employees.

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 Beacon who are expected to be retained by BHLB.  BHLB may not be successful in retaining these employees for the time period necessary to successfully integrate Beacon’s operations with those of BHLB.  The diversion of management’s attention and any delays or difficulties 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 BHLB following the merger.

The termination fee and the restrictions on solicitation contained in the merger agreement may discourage other companies from trying to acquire Beacon.

Until the completion of the merger, with some exceptions, Beacon is prohibited from soliciting, initiating, encouraging or participating in any discussion of or otherwise considering any inquiries or proposals that may lead to an acquisition proposal, such as a merger or other business combination transaction, with any person other than BHLB.  In addition, Beacon has agreed to pay a termination fee to BHLB in specified circumstances. These provisions could discourage other companies from trying to acquire Beacon even though those other companies might be willing to offer greater value to Beacon’s shareholders than BHLB has offered in the merger. The payment of the termination fee could also have a material adverse effect on Beacon’s financial condition.

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

You should be aware that the directors and officers of Beacon have interests in the merger that are different from, or in addition to, the interests of Beacon shareholders generally.  These include: severance payments that certain officers may receive under existing employment agreements; possible accelerated vesting of stock options; provisions in the merger agreement relating to indemnification of directors and officers and insurance for directors and officers of Beacon for events occurring before the merger; the appointment of one Beacon board member to the boards of BHLB and Berkshire Bank; and the appointment of Beacon board members to the BHLB advisory board of directors.  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 54.

If you are a Beacon shareholder and you make a valid cash or stock election, you will not be able to sell your shares during certain times.

If you are a Beacon shareholder of record as of the record date for the special meeting, hold your shares in certificated form and want to make a valid cash or stock election, you will have to deliver a properly completed and signed form of election and your stock certificates to the exchange agent. For further details on the determination of the election deadline, see “Description of the Merger—Election Procedures; Surrender of Stock Certificates” on page 48. The election deadline will be the later of the day of the Beacon special meeting and the date the parties believe to be as near as practicable to five business days before the completion of the merger. You will not be able to sell any certificated shares of Beacon common stock that you have delivered as part of your election unless you revoke your election before the deadline by providing written notice to the exchange agent. If you do not revoke your election before the election deadline, you will not be able to liquidate your investment in Beacon common stock for any reason until you receive cash and/or BHLB common stock following completion of the merger. Similarly, holders of book-entry shares of Beacon common stock who have made a valid election and have not revoked their election prior to the election deadline will not be able to sell any shares for which they have made a valid election after the election deadline. In the time between the election deadline and the completion of the merger, the trading price of Beacon or BHLB common stock may decrease, and you might otherwise want to sell your shares of Beacon common stock to gain access to cash, make other investments, or reduce the potential for a decrease in the value of your investment. The date that you will receive your merger consideration depends on the completion date of the merger, which is uncertain. The completion date of the merger might be later than expected due to unforeseen events, such as delays in obtaining regulatory approvals.

Failure to complete the merger could negatively impact the stock prices and future businesses and financial results of BHLB and Beacon.

If the merger is not completed, the ongoing businesses of BHLB and Beacon may be adversely affected and BHLB and Beacon will be subject to several risks, including the following:

·                  BHLB and Beacon will be required to pay certain costs relating to the merger, whether or not the merger is completed, such as legal, accounting, financial advisor and printing fees;

·                  under the merger agreement, Beacon is subject to certain restrictions on the conduct of its business prior to completing the merger, which may adversely affect its ability to execute certain of its business strategies; and

·                  matters relating to the merger may require substantial commitments of time and resources by BHLB and Beacon management, which could otherwise have been devoted to other opportunities that may have been beneficial to BHLB and Beacon as independent companies, as the case may be.

In addition, if the merger is not completed, BHLB and/or Beacon may experience negative reactions from the financial markets and from their respective customers and employees. BHLB and/or Beacon also could be subject to litigation related to any failure to complete the merger or to enforcement proceedings commenced against BHLB or Beacon to perform their respective obligations under the merger agreement. If the merger is not completed, BHLB and Beacon cannot assure their shareholders that the risks described above will not materialize and will not materially affect the business, financial results and stock prices of BHLB and/or Beacon.

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The shares of BHLB common stock to be received by Beacon shareholders receiving the stock consideration as a result of the merger will have different rights from shares of Beacon common stock.

Following completion of the merger, Beacon shareholders who receive the stock consideration will no longer be shareholders of Beacon, a Maryland corporation, but will instead be shareholders of BHLB, a Delaware corporation. There will be important differences between your current rights as a Beacon shareholder and the rights to which you will be entitled as a BHLB shareholder. See “Comparison of Rights of Shareholders” beginning on page 67 for a discussion of the different rights associated with BHLB common stock and Beacon common stock.

The fairness opinion obtained by Beacon from its financial advisor will not reflect changes in circumstances subsequent to the date of the fairness opinion.

KBW, Beacon’s financial advisor in connection with the merger, has delivered to the board of directors of Beacon its opinion dated as of May 31, 2012. 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 Beacon 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 BHLB or Beacon, 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 BHLB and Beacon.

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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,” and “Description of the Merger—Beacon’s Reasons for the Merger and Recommendation of the Board of Directors.”  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 11.

Additional factors that could cause the results of BHLB or Beacon to differ materially from those described in the forward looking statements can be found in the filings made by BHLB and Beacon with the Securities and Exchange Commission, including the BHLB Annual Report on Form 10-K for the fiscal year ended December 31, 2011, the Beacon Annual Report on Form 10-K for the fiscal year ended December 31, 2011, the BHLB Quarterly Report on Form 10-Q for the quarter ended March 31, 2012 and the Beacon Quarterly Report on Form 10-Q for the quarter ended March 31, 2012.

Because of these and other uncertainties, actual results, performance or achievements, or industry results, may be materially different from the results indicated by these forward-looking statements. In addition, BHLB’s and Beacon’s past results of operations do not necessarily indicate BHLB’s and Beacon’s combined future results. You should not place undue reliance on any forward-looking statements, which speak only as of the dates on which they were made.  BHLB and Beacon are not 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. All forward-looking statements are qualified by these cautionary statements.

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SELECTED HISTORICAL FINANCIAL INFORMATION

The following tables show summarized historical financial data for BHLB and Beacon. You should read this summary financial information in conjunction with BHLB’s consolidated financial statements and the notes thereto in reports that BHLB has previously filed with the SEC.  Historical financial information for BHLB can be found in its Quarterly Report on Form 10-Q for the quarter ended March 31, 2012 and its Annual Report on Form 10-K for the year ended December 31, 2011, which are incorporated by reference into this document.

You should read this summary financial information in conjunction with Beacon’s consolidated financial statements and the notes thereto in reports that Beacon has previously filed with the SEC.  Historical financial information for Beacon can be found in its Quarterly Report on Form 10-Q for the quarter ended March 31, 2012 and its Annual Report on Form 10-K for the year ended December 31, 2011, which are incorporated by reference into this document.

Unaudited consolidated interim financial statements for BHLB and Beacon at or for the three months ended March 31, 2012 and 2011 include normal, recurring adjustments necessary to fairly present the data for those periods.  The unaudited data is not necessarily indicative of expected results of a full year’s operation.

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

Note:  BHLB acquired Rome Bancorp, Inc. on April 1, 2011 and Legacy Bancorp, Inc. on July 21, 2011.  Financial data includes acquired balances as of March 31, 2012, along with the impact of equity issued as merger consideration.  Operating data includes the operations of the acquired banks beginning as of the acquisition dates, as well as non-recurring income and expenses related to these merger events. BHLB acquired The Connecticut Bank and Trust Company (“CBT”) and certain assets, liabilities and operations of Greenpark Mortgage Corporation (“Greenpark”) in April 2012.  The financial data above does not include the effects of these transactions.

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Note: All performance ratios are based on average balance sheet amounts where applicable.  2011 data includes balances associated with discontinued operations.

All information for three month periods is annualized where applicable.

(1)              Loans do not include loans held for sale, which are not material.

(2)              Net income (loss) divided by average total assets.

(3)              Net income (loss) divided by average total equity.

(4)              Net interest rate spread represents the difference between the weighted average yield on interest-earning assets and the weighted average cost of interest-bearing liabilities.

(5)              Net interest margin represents net interest income as a percentage of average interest-earning assets for the period.

Note:  Generally accepted accounting principles require that acquired loans be recorded at fair value.  In 2011, BHLB acquired loans as a result of its acquisitions of Rome Bancorp and Legacy Bancorp.  The fair value of acquired loans includes expected loan losses, and there is no loan loss allowance recorded for acquired loans at the time of acquisition.  Accordingly, the ratio of the loan loss allowance to total loans is reduced as a result of the existence of acquired loans, and this measure is not directly comparable to prior periods.  Similarly, net loan charge-offs are normally reduced for acquired loans since these loans are recorded net of expected loan losses.  Therefore, the ratio of net loan charge-offs to average loans is reduced as a result of the existence of acquired loans, and this measure is not directly comparable to prior periods.  Other institutions may have acquired loans, and therefore there may be no direct comparability of these ratios between and among other institutions. BHLB acquired CBT and certain assets, liabilities and operations of Greenpark in April 2012.  The financial data above does not include the effects of these transactions.

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SELECTED HISTORICAL FINANCIAL AND OTHER DATA OF BEACON FEDERAL BANCORP, INC.

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