SEC FORM 4

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

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Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

1. Name and Address of Reporting Person^*

DALY MICHAEL P

(Last)

(First)

(Middle)

24 NORTH ST

(Street)

PITTSFIELD

01201

(City)

(State)

(Zip)

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

3. Date of Earliest Transaction (Month/Day/Year)
12/12/2008

4. If Amendment, Date of 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

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)
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	Amount	(A) or (D)	Price		6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
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⁾

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 Securities Underlying Derivative Security (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: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
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)	Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares	8. Price of Derivative Security (Instr. 5)		10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
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

Explanation of Responses:

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.

	/s/ Michael P. Daly	12/16/2008
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* 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).
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