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Berkshire Bank - America's Most Exciting Bank(SM) - Presented at Sandler O'Neill 2007 East Coast Financial Services Conference

Berkshire Hills Bancorp (BHLB) made a presentation about the Company and its subsidiary, Berkshire Bank - AMERICA'S MOST EXCITING BANKSM - on November 13, 2007 at the 2007 East Coast Financial Services Conference hosted by Sandler ONeill + Partners.

President and Chief Executive Officer, Michael P. Daly, reported on the gains in core earnings per share for the first nine months of the year, and he discussed the expected benefit to future earnings from the positive operating leverage generated in the most recent quarter. He reviewed the major steps in Berkshires growth, including the recently completed acquisition of Factory Point Bancorp in Southern Vermont. Berkshire has grown from 11 to 48 stores - operating as a multi-state regional financial institution providing banking, insurance, and wealth management services. Mr. Daly pointed out the Company's history of conservative asset quality management, and he noted that the Company has no sub-prime lending programs. He reiterated Berkshires long term goal of double-digit growth in core earnings per share. Mr. Daly concluded by noting that at current pricing levels, Berkshires stock is a very attractive investment for the Company and he reported that the Company is moving forward with stock repurchases under its approved program.

A video webcast of the presentation may be viewed by visiting the Investor Relations tab at Berkshires web site, www.berkshirebank.com, and a copy of the presentation slides is also available at this site.

BACKGROUND

Berkshire Hills Bancorp is the holding company for Berkshire Bank - AMERICA'S MOST EXCITING BANKSM. Established in 1846, Berkshire Bank is one of Massachusetts' oldest and largest independent banks and the largest banking institution based in Western Massachusetts. The Bank is headquartered in Pittsfield, Massachusetts with branches serving communities throughout Western Massachusetts, Northeastern New York and Southern Vermont. The Bank is transitioning into a regional bank, delivering exceptional customer service and a broad array of competitively priced deposit, loan, insurance, wealth management and trust services and investment products. For more information on Berkshire Hills Bancorp or Berkshire Bank, visit www.berkshirebank.com or call 800-773-5601.

FORWARD-LOOKING STATEMENTS

Statements made in the presentation may have contained forward-looking statements within the meaning of the Private Securities Litigation Reform Act of 1995. Forward-looking statements can be identified by the fact that they do not relate strictly to historical or current facts. They often include words like believe,guidance, expect,anticipate, estimate, and intend or future or conditional verbs such as will,would, should,could or may. These statements are based on the beliefs and expectations of management. Since these statements reflect the views of management concerning future events, these statements involve risks, uncertainties, and assumptions. These risks and uncertainties include among others: changes in market interest rates and general and regional economic conditions; changes in government regulations; changes in accounting principles; the quality or composition of the loan and investment portfolios; and the achievement of anticipated future earnings benefits from recent acquisitions. In addition, the following factors, among others, could cause actual results to differ materially from the anticipated results or other expectations expressed in the forward-looking statements: adverse governmental or regulatory policies may be enacted; the risks associated with continued diversification of assets and adverse changes to credit quality; and difficulties associated with achieving expected future financial results. Additionally, other risks and uncertainties may be described in the Companys quarterly reports on Form 10-Q for the quarters ended March 31, June 30, and September 30 and in its annual report on Form 10-K, each filed with the Securities and Exchange Commission, which are available at the Securities and Exchange Commissions internet website (www.sec.gov) and to which reference is hereby made. Therefore, actual future results may differ significantly from results discussed in these forward-looking statements and undue reliance should not be placed on such statements. The Company assumes no obligation to update any forward-looking statements.

Statements made in the presentation may also have contained certain forward-looking statements about the merger of Berkshire Hills Bancorp and Factory Point Bancorp. These statements include anticipated future operating results. Certain factors that could cause actual results to differ materially from expected results include delays, difficulties in achieving cost savings from the merger or in achieving such cost savings within the expected time frame, difficulties in integrating Berkshire Hills Bancorp and Factory Point, increased competitive pressures, changes in the interest rate environment, changes in general economic conditions, legislative and regulatory changes that adversely affect the business in which Berkshire Hills Bancorp is engaged, changes in the securities markets and other risks and uncertainties disclosed from time to time in documents that Berkshire Hills Bancorp files with the Securities and Exchange Commission.

NON-GAAP FINANCIAL MEASURES

The presentation contained statements about certain non-GAAP financial measures in addition to results presented in accordance with Generally Accepted Accounting Principles (GAAP). The Companys management uses certain non-GAAP measures for operational and investment decisions and believes that these measures are among several useful measures for understanding its operating results, performance trends, and financial condition. These measures should not be construed as a substitute for GAAP measures; they should be read and used in conjunction with the Companys GAAP financial information. A reconciliation of non-GAAP financial measures to GAAP measures is included in the Companys most recent quarterly earnings release. In all cases, it should be understood that non-GAAP per share measures do not depict amounts that accrue directly to the benefit of shareholders. The Company utilizes the non-GAAP measure of core earnings in evaluating operating trends during the current fiscal period, and compared to the prior fiscal period. The core earnings measure is not intended to substitute for GAAP net income, but is an additional measure that the Company uses and believes is useful for understanding its operating results. During the third quarter of 2006, the Company identified charges related to the balance sheet repositioning and to the loan loss allowance adjustment as non-core in the computation of core earnings. The Company views these charges as infrequent and not specifically related to the Companys operating activities during the year. During the third quarter of 2007, the Company identified charges in conjunction with the acquisition of Factory Point Bancorp as non-core in the computation of core earnings. These charges included indirect merger costs and balance sheet deleveraging costs. Additionally, expense restructuring costs were deemed as non-core.

Contacts:

Berkshire Hills Bancorp
David H. Gonci, 413-281-1973
Corporate Finance Officer

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