Ownership Submission
FORM 4
Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).
UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP OF SECURITIES

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934, Section 17(a) of the Public Utility Holding Company Act of 1935 or Section 30(h) of the Investment Company Act of 1940
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(Print or Type Responses)
1. Name and Address of Reporting Person *
DALY MICHAEL P
  2. Issuer Name and Ticker or Trading Symbol
BERKSHIRE HILLS BANCORP INC [BHLB]
5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)
__X__ Director _____ 10% Owner
__X__ Officer (give title below) _____ Other (specify below)
President and CEO
(Last)
(First)
(Middle)
24 NORTH ST
3. Date of Earliest Transaction (Month/Day/Year)
12/12/2008
(Street)

PITTSFIELD, MA 01201
4. If Amendment, Date Original Filed(Month/Day/Year)
6. Individual or Joint/Group Filing(Check Applicable Line)
_X_ Form filed by One Reporting Person
___ Form filed by More than One Reporting Person
(City)
(State)
(Zip)
Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1.Title of Security
(Instr. 3)
2. Transaction Date (Month/Day/Year) 2A. Deemed Execution Date, if any (Month/Day/Year) 3. Transaction Code
(Instr. 8)
4. Securities Acquired (A) or Disposed of (D)
(Instr. 3, 4 and 5)
5. Amount of Securities Beneficially Owned Following Reported Transaction(s)
(Instr. 3 and 4)
6. Ownership Form: Direct (D) or Indirect (I)
(Instr. 4)
7. Nature of Indirect Beneficial Ownership
(Instr. 4)
Code V Amount (A) or (D) Price
Common Stock 12/12/2008   P   7,241 (6) (7) A $ 27.2512 15,756 (1) I By 401(k)
Common Stock 12/12/2008   P   6,100 (6) (7) A $ 26.3665 71,946 D  
Common Stock 12/12/2008   S   638 (6) (7) D $ 26.25 71,308 D  
Common Stock 12/12/2008   S   5,462 (6) (7) D $ 26.4 65,846 D  
Common Stock 12/12/2008   S   979 (6) (7) D $ 27.08 64,867 D  
Common Stock 12/12/2008   S   400 (6) (7) D $ 27.09 64,467 D  
Common Stock 12/12/2008   S   200 (6) (7) D $ 27.12 64,267 D  
Common Stock 12/12/2008   S   1,400 (6) (7) D $ 27.15 62,867 D  
Common Stock 12/12/2008   S   200 (6) (7) D $ 27.17 62,667 D  
Common Stock 12/12/2008   S   200 (6) (7) D $ 27.21 62,467 D  
Common Stock 12/12/2008   S   100 (6) (7) D $ 27.24 62,367 D  
Common Stock 12/12/2008   S   3,221 (6) (7) D $ 27.25 59,146 D  
Common Stock 12/12/2008   S   100 (6) (7) D $ 27.3 59,046 D  
Common Stock 12/12/2008   S   100 (6) (7) D $ 27.32 58,946 D  
Common Stock 12/12/2008   S   200 (6) (7) D $ 27.33 58,746 D  
Common Stock 12/12/2008   S   200 (6) (7) D $ 27.4 58,546 D  
Common Stock               1,666 I By Stock Award V (2)
Common Stock               6,054 I By Stock Award VI (3)
Common Stock               5,608 I By Stock Award VII (4)

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Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned
(e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security
(Instr. 3)
2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (Month/Day/Year) 3A. Deemed Execution Date, if any (Month/Day/Year) 4. Transaction Code
(Instr. 8)
5. Number of Derivative Securities Acquired (A) or Disposed of (D)
(Instr. 3, 4, and 5)
6. Date Exercisable and Expiration Date
(Month/Day/Year)
7. Title and Amount of Underlying Securities
(Instr. 3 and 4)
8. Price of Derivative Security
(Instr. 5)
9. Number of Derivative Securities Beneficially Owned Following Reported Transaction(s)
(Instr. 4)
10. Ownership Form of Derivative Security: Direct (D) or Indirect (I)
(Instr. 4)
11. Nature of Indirect Beneficial Ownership
(Instr. 4)
Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares
Stock Option (right-to-buy) $ 16.75             01/30/2002(5) 01/30/2011 Common Stock 8,519   8,519 D  
Stock Option (right-to-buy) $ 22.3             01/30/2004(5) 01/30/2013 Common Stock 41,481   41,481 D  
Stock Option (right-to-buy) $ 37.8             01/30/2006(5) 01/30/2014 Common Stock 6,000   6,000 D  

Reporting Owners

Reporting Owner Name / Address Relationships
 Director  10% Owner  Officer  Other
DALY MICHAEL P
24 NORTH ST
PITTSFIELD, MA 01201
  X     President and CEO  

Signatures

 /s/ Michael P. Daly   12/16/2008
**Signature of Reporting Person Date

Explanation of Responses:

* If the form is filed by more than one reporting person, see Instruction 4(b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations. See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
(1) This form reflects increases in beneficial ownership resulting from exempt acquisitions pursuant to Rule 16b-3(c).
(2) Stock Awards granted pursuant to the Berkshire Hills Bancorp, Inc. 2003 Equity Compensation Plan vest in three equal annual installments commencing on January 30, 2007.
(3) Stock Awards granted pursuant to the Berkshire Hills Bancorp, Inc. 2003 Equity Compensation Plan vest in four equal annual installments beginning on January 30, 2008.
(4) Stock Awards granted pursuant to the Berkshire Hills Bancorp, Inc. 2003 Equity Compensation Plan vest in three equal annual installments commencing on January 30, 2009.
(5) Stock Options are fully vested and exercisable.
(6) The reporting person's sale was matchable under Section 16(b) of the Securities Exchange Act of 1934, as amended, to the extent of 1,000 and 6,100 shares, respectively, with the reporting person's purchase of 1,000 shares of Berkshire Hills Bancorp, Inc. common stock at a price of $23.9304 per share on October 28, 2008 and 6,100 shares at a various prices between 27.08 and 27.25 on December 12, 2008. The reporting person has agreed to pay Berkshire Hills Bancorp, Inc. $8,379.52, representing the full amount of profit realized in connection with the short-swing transaction.
(7) The transactions covered by this Form 4 did not result in a material change in the total number of securities beneficially owned by Mr. Daly. These transactions were conducted for estate planning purposes; the transactions effectively transferred stock from after-tax accounts to tax-qualified accounts.

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