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FOR IMMEDIATE RELEASE

                BERKSHIRE HILLS BANCORP COMPLETES ACQUISITION OF
                             FIVE INSURANCE AGENCIES


PITTSFIELD, MA (BUSINESS WIRE) - November 3, 2006 - Berkshire Hills Bancorp,
Inc. (the "Company") (NASDAQ: BHLB) the holding company for Berkshire Bank,
announced today that it completed its acquisition of five insurance agencies on
October 31, 2006. The agencies acquired by the Company's wholly-owned
subsidiary, Berkshire Insurance Group, Inc., are Reynolds, Barnes & Hebb and
McCormick, Smith & Curry of Pittsfield, Minkler Insurance of Stockbridge, and
H.S. Andrews of Great Barrington (all in Berkshire County) and MassOne of
Greenfield (located in adjoining Franklin County). Berkshire Insurance Group now
operates through ten offices throughout the Berkshires and the Pioneer Valley of
Western Massachusetts.

Michael P. Daly, President and Chief Executive Officer of the Company and
Berkshire Bank, stated "It is my pleasure to welcome customers and employees of
these five agencies to Berkshire Insurance Group. We are delighted that we were
able to close these deals so quickly after signing the definitive agreements.
That was brought about by energetic and cooperative groups of insurance and bank
employees who share the same values, culture and work ethic. All management and
other personnel of the five agencies are now part of our insurance team, headed
by insurance group President and Chief Executive Officer, Ross Gorman."

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Berkshire Hills Bancorp, Inc. is the holding company for Berkshire Bank.
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 and Northeastern
New York. The Bank is transitioning into a regional bank and is positioning
itself as the financial institution of choice in its retail and commercial
markets, 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, Inc. or Berkshire Bank, visit www.berkshirebank.com or call
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800-773-5601.

Statements contained in this news release contain forward-looking statements
within the meaning of the Private Securities Litigation Reform Act of 1995.
These statements are based on the beliefs and expectations of management, as
well as the assumptions made using information currently available to
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; and the quality or composition of
the loan and investment portfolios and other factors that may be described in
the Company's quarterly reports on Form 10-Q for the quarters ended March 31,
June 30, 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 Commission's Internet Web site (WWW.SEC.GOV) and to which reference
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is hereby made. Therefore, actual future results may differ significantly from
results discussed in these forward-looking statements.

CONTACT: Berkshire Hills Bancorp, Inc.
         Michael P. Daly, 413-236-3194
         President and Chief Executive Officer