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                 BERKSHIRE BANK NAMES VETERAN ALBANY AREA BANKER
                     TO LEAD NEW YORK REGION AND ESTABLISHES
                      DOWNTOWN ALBANY REGIONAL HEADQUARTERS

               THOMAS C. CROWLEY NAMED PRESIDENT - NEW YORK REGION

PITTSFIELD, MA - November 16, 2005 - Berkshire Hills Bancorp, Inc. (the
"Company") (NASDAQ: BHLB), the holding company for Berkshire Bank (the "Bank"),
today announced the hiring of veteran Albany area banker Thomas C. Crowley as
its President-New York Region and that it has made its New York operation a
separate business unit headquartered at 41 State Street in downtown Albany, with
local management and commercial lending decisions.

Crowley has over 25 years of banking experience, including 14 years with Fleet
Bank followed by five years with Evergreen Bank as its Executive Vice President
and Chief Credit Officer. A native New Yorker now living in Jackson, New York,
Crowley received his MBA in Finance and Marketing and his B.A. in Economics from
the University of Notre Dame.

Crowley's office is located at 41 State Street. He joins Bruce C. Peck, Vice
President and Commercial Loan Officer, who started the Bank's commercial lending
operations in New York in 2003 and has since then participated in the
origination of over $80 million in commercial loans, and Kenneth J. Cartledge,
Vice President and Commercial Loan Officer, who joined the Bank in September
2005.

Commenting on these moves, Michael P. Daly, President and Chief Executive
Officer of the Company and the Bank stated, "Tom Crowley brings immediate
legitimacy to Berkshire Bank in New York and the addition of a regional
president to our team is the natural progression in our growth and commitment as
a top-tier, financial services company with local decision-making. Tom is
developing a team of experienced, local commercial lenders that will provide the
best service possible to our customers. We are very optimistic about our
prospects in the Capital Region and are excited that Tom will lead our efforts
there. We are committed to growing our franchise in Albany and the surrounding
areas and look forward to establishing an advisory board of local business
leaders and residents in the near future."

Mr. Daly added, "Being a Massachusetts-chartered bank means we offer total
deposit insurance coverage. While we are of course a member of the Federal
Deposit Insurance Corporation (FDIC) we are also a member of the Massachusetts
Depositors Insurance Fund (DIF), which insures all deposits in excess of the
FDIC limits. To our knowledge, we are the only bank in New York offering DIF
coverage to depositors. Looking ahead, we remain focused on executing our
business strategies, including:

|X| Expanding our presence in the New York market;
|X| Hiring the best bankers in the New York market;

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|X| Delivering impeccable customer service that is second to none in the areas
    of commercial, consumer and municipal banking;
|X| Offering our Trusted Solutions SM array of sophisticated banking products
    and highly competitive rates with local decision-making;
|X| Continuing the Bank's philanthropic efforts and commitment to the
    communities we serve."

As a result of the actions announced today, the Bank expects to convert its
representative office at 54 State Street, Albany into its new regional
headquarters at 41 State Street prior to the end of next month. The Bank opened
its representative office in July 2004 as a precursor to establishing
full-services branches in New York.

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
branch offices serving communities throughout Western Massachusetts and
Northeastern New York and a representative office in New York. The Bank is
committed to operating as an independent super community bank, delivering
exceptional customer service, and offering a broad array of competitively priced
retail and commercial products to its customers.

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 that may be described in the Company's
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 Commission's internet website (WWW.SEC.GOV) and to which reference is
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hereby made. Therefore, actual future results may differ significantly from
results discussed in these forward-looking statements.

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