1108134--3/16/2009--BERKSHIRE_HILLS_BANCORP

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Continued and Prolonged Deterioration in the Housing Sector and Related Markets and the Economy May Adversely Affect Our Business and Financial Results. Our Emphasis on Commercial Lending May Expose Us to Increased Lending Risks, Which Could Hurt Our Profits. Our Allowance for Loan Losses May Prove to be Insufficient to Absorb Losses in Our Loan Portfolio. A Continuing Downturn in the Local Economy or Local Real Estate Values Could Hurt Our Profits. Our Geographic Expansion and Growth, If Not Successful, Could Negatively Impact Earnings. Competition From Financial Institutions and Other Financial Service Providers May Adversely Affect Our Growth and Profitability. The Terms of Our Capital May Change and Our Access to Capital Markets and Financial Markets May Not Be Available When It Is Needed. We are Subject to Security and Operational Risks Relating to Our Use of Technology that Could Damage Our Reputation and Our Business. Conditions in Insurance Markets Could Adversely Affect Our Earnings. Our Wholesale Funding Sources May Prove Insufficient to Replace Deposits at Maturity and Support Our Operations and Future Growth. Lack of Consumer Confidence in Financial Institutions May Decrease Our Level of Deposits. Our Ability to Service Our Debt, Pay Dividends and Otherwise Pay Our Obligations as They Come Due Is Substantially Dependent on Capital Distributions from Berkshire Bank, and These Distributions Are Subject to Regulatory Limits and Other Restrictions. Economic Conditions May Adversely Affect Our Liquidity. Changes in Interest Rates Could Adversely Affect Our Results of Operations and Financial Condition. Continued or Further Declines in the Value of Certain Investment Securities Could Require Write-Downs, Which Would Reduce Our Earnings. If Dividends Paid On Our Investment in the Federal Home Loan Bank of Boston Continue to be Suspended, or If Our Investment is Classified as Other-Than-Temporarily Impaired or as Permanently Impaired, Our Earnings and/or Stockholders Equity Could Decrease. Recent Legislative and Regulatory Initiatives May Not Stabilize the Banking System. Future Legislative or Regulatory Actions Responding to Perceived Financial and Market Problems Could Impair Our Rights Against Borrowers. Our Expenses Will Increase As A Result Of Increases in FDIC Insurance Premiums. Changes In Federal Statutes May Adversely Affect the Terms of our Capital Purchase Program Letter Agreement with the U.S. Treasury. Provisions of our certificate of incorporation, bylaws and Delaware law, as well as state and federal banking regulations, could delay or prevent a takeover of us by a third party. Our Acquisitions Have Resulted in Significant Goodwill, Which if it Becomes Impaired Would be Required to be Written Down, Which Would Negatively Impact Earnings. The Trading History of Our Common stock is Characterized by Low Trading Volume. The Value of Your Investment May be Subject to Sudden Decreases Due to the Volatility of the Price of our Common Stock.

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1108134--3/16/2009--BERKSHIRE_HILLS_BANCORP_INC