Berkshire Hills Bancorp (BHLB)

Announces Common Stock Offering

Pittsfield, MA, October 6, 2008 – Berkshire Hills Bancorp, Inc. (NASDAQ: BHLB) announced today that it has commenced a public offering of approximately $30 million of its common stock. This is a drawdown under the $125 million SEC shelf registration that Berkshire filed in 2006 to facilitate stock issuances for growth opportunities.

Berkshire’s President and Chief Executive Officer Michael P. Daly stated, “This has been an exceptionally good year for Berkshire despite the changes in the financial and economic landscape. Therefore, it is timely and appropriate for us to bolster our balance sheet in anticipation of growth opportunities that we think may develop as a result of current events.”

The Company has also granted the underwriters of the offering a 30-day option to purchase up to an additional 15% of the shares sold to cover over-allotments, if any. The shares will be issued pursuant to a prospectus filed as part of the Company’s registration statement on Form S-3.

The net proceeds of the offering will be used to pursue growth opportunities and for general corporate purposes.

Sandler O’Neill + Partners, L.P. is acting as lead book-running manager and Keefe, Bruyette & Woods, Inc. is a co-manager for the offering.

The common stock offering may be made only by means of a prospectus and related prospectus supplement. Copies of the preliminary prospectus supplement and the prospectus relating to the offering may be obtained from Sandler O’Neill + Partners, L.P., 919 Third Avenue, 6th Floor, New York, NY 10022.