Exhibit 99.1

Berkshire Hills Reports 46 Cents Third Quarter Core EPS;

Dividend Declared

PITTSFIELD, MASS, October 27, 2014 — Berkshire Hills Bancorp, Inc. (NYSE: BHLB) reported a 5% increase in core earnings per share to $0.46 in the third quarter of 2014 from $0.44 in the prior quarter.  Third quarter core EPS advanced by 7% year-over-year.  Berkshire continues to generate higher revenue as it builds business volumes across its regional markets.  GAAP EPS was $0.48 in the third quarter of 2014 and $0.46 in the prior quarter, reflecting the $0.02 per share quarterly benefit of a lower GAAP tax rate that resulted from non-core branch acquisition related costs in the first quarter.

THIRD QUARTER FINANCIAL HIGHLIGHTS (comparisons are to prior quarter):

·              5% increase in core earnings per share

·              5% annualized increase in net revenue

·              9% annualized increase in total loans

·              8% annualized increase in deposits

·              6% increase in demand deposits

·              0.44% non-performing assets/assets

·              0.28% net loan charge-offs/average loans

CEO Michael Daly stated, “Core EPS has grown by $0.02 per share in each of the last three quarters and is now up 15% compared to the $0.40 result in the fourth quarter of 2013.  We continue to generate solid revenue growth from business expansion which is illustrated by balance sheet growth and year-over-year gains in all categories of fee income.”

Mr. Daly continued, “The Berkshire team was strengthened across our franchise in the third quarter.  A five person small business banking team joined us in Albany, following our first quarter branch purchase in New York.    We recruited a senior commercial real estate lender in Hartford and added wealth management professionals in several Massachusetts markets.  Our strong electronic banking solution was enhanced with the addition of a leading online fraud protection service, and we added to our solutions for mobile customers.  Our company’s initiatives were recognized with several marketing, communications and philanthropic awards, and our growing small business banking team was named the top SBA lender in Western Massachusetts.  In addition, we recently

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opened a new branch located within our Westborough office, which serves as the regional headquarters in our Central Massachusetts market.”

Mr. Daly concluded, “Our management disciplines are evidenced by improvement in our efficiency ratio and return on assets, together with further strengthening of our asset quality metrics.  I’m excited about our many opportunities to deliver on our brand promise to our markets and to further boost bottom line results for our investors.”

DIVIDEND DECLARED

The Board of Directors voted to declare a cash dividend of $0.18 per share to shareholders of record at the close of business on November 13, 2014, payable on November 26, 2014.  This dividend equates to a 3.0% annualized yield based on the $24.02 average closing price of Berkshire’s common stock during the third quarter.

FINANCIAL CONDITION

In the most recent quarter, Berkshire produced annualized growth of 9% for total loans and 8% for total deposits.  Measures of capital, asset quality, liquidity, and interest rate sensitivity remained solid.  Tangible book value per share increased during the quarter by 2% to $16.67 and total book value per share increased by 1% to $27.69.  Berkshire’s assets totaled $6.4 billion at quarter-end.

Berkshire recorded organic growth in all major loan categories in the most recent quarter.  Total commercial loans increased at a 4% annualized rate, bringing year-to-date annualized growth to 14%.  Both commercial real estate and commercial and industrial balances advanced for the quarter and year-to-date.  Commercial activity has been spread across the franchise, with the strongest third quarter production in Eastern Massachusetts and New York.  Residential mortgage balances advanced on higher originations volume.  Consumer loan balances benefited from ongoing indirect auto originations together with improved home equity outstandings.  Total consumer balances grew at an 18% annualized rate in the third quarter, bringing the year-to-date annualized growth rate to 17%.

Asset quality metrics remained favorable.  Annualized net loan charge-offs measured 0.28% of average loans for the quarter.   Quarter-end non-performing assets decreased to 0.44% of total assets and accruing delinquent loans decreased to 0.44% of total loans.  The loan loss allowance remained at 0.77% of total loans; approximately 18% of quarter-end loans were balances recorded at fair value in recent bank acquisitions.

Annualized deposit growth of 8% in the third quarter was driven primarily by demand deposits and time accounts.  Demand deposit balances increased at a strong 25% annualized rate, including growth in commercial balances following the significant increase in commercial lending balances over the year.   Berkshire promotes its non-interest bearing checking accounts as a focus for relationship acquisition and

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enhancement.  Time deposit growth was accompanied by a 7 basis point decrease in the cost of these deposits during the quarter.

Investment securities, cash balances, and borrowings were all reduced during the quarter.  At quarter-end, the ratio of loans/deposits stood at 100%.  The ratio of equity/assets increased to 11.0% and tangible equity/assets improved to 6.9%.

RESULTS OF OPERATIONS

Third quarter 2014 core earnings increased by 4% to $11.4 million, or $0.46 per share, from $10.9 million, or $0.44 per share, in the prior quarter.  Third quarter core earnings per share increased by 7% from $0.43 in 2013.  Non-core charges related to the bank’s recent charter change were offset by securities gains.  GAAP earnings in the most recent quarter totaled $12.0 million, or $0.48 per share.   GAAP EPS totaled $0.46 in the second quarter of 2014 and $0.33 in the third quarter of 2013.

The core return on tangible equity improved to 11.8% in the most recent quarter, representing the third consecutive quarterly increase in this metric.  The GAAP return on equity improved to 7.0% which was the highest result in the last five quarters.  The efficiency ratio improved to 62.89% from 62.96% in the prior quarter.

Third quarter net revenue increased by 1% compared to the prior quarter, including 1% increases in both net interest income and non-interest income.  Growth in net interest income was driven by the 2% increase in average earning assets resulting from loan growth.  The net interest margin decreased to 3.20% in the third quarter from 3.26% in the prior quarter.  This decrease was primarily due to lower interest rates on newly originated mortgages and consumer loans reflecting the ongoing impact of the interest rate environment.  Net interest income includes purchased loan accretion which is largely comprised of recoveries on the resolution of impaired loans purchased in previous bank acquisitions.  This accretion totaled $1.2 million in the most recent quarter, compared to $1.0 million in the prior quarter, and it contributed 0.08% and 0.07% to the margin in these respective quarters.

Third quarter fee income was unchanged from the prior quarter.  Mortgage banking revenue rose on higher business volume which benefited from an expanded originations team and product set.  This growth offset the decrease in commercial loan interest rate swap income related to the elevated second quarter commercial loan growth.  Total third quarter fee income increased by 27% year-over-year.  This included organic growth in all major categories along with the benefit of the New York branch acquisition in January 2014.

The loan loss provision totaled $3.7 million in the third quarter, decreasing from $4.0 million in the prior quarter due to higher second quarter loan growth.  Third quarter net loan charge-offs totaled $3.1 million, and the loan loss allowance increased by $0.6 million.

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Third quarter non-interest expense increased by 1% over the prior quarter primarily due to increased compensation expense related to business expansion.  The core tax rate was 30% in both periods and the GAAP tax rate was 26% due to the full year impact of the first quarter branch acquisition charges.

CONFERENCE CALL

Berkshire will conduct a conference call/webcast at 10:00 a.m. eastern time on Tuesday, October 28, 2014 to discuss the results for the quarter and provide guidance about expected future results. Participants should dial-in to the call 10-15 minutes before it begins. Information about the conference call follows:

Dial-in:  888-317-6003

Elite Entry Number:  4239712

Webcast:  berkshirebank.com (investor relations link)

A telephone replay of the call will be available through Wednesday, November 5, 2014 by calling 877-344-7529 and entering conference number: 10053457. The webcast will be available at Berkshire’s website above for an extended period of time.  A print-friendly version of this news release will be available at the web link shown above.

BACKGROUND

Berkshire Hills Bancorp is the parent of Berkshire Bank — America’s Most Exciting Bank®.  The Company has $6.4 billion in assets and 91 full-service branch offices in Massachusetts, New York, Connecticut, and Vermont providing personal and business banking, insurance, and wealth management services.

FORWARD LOOKING STATEMENTS

This document contains forward-looking statements as defined in the Private Securities Litigation Reform Act of 1995.  There are several factors that could cause actual results to differ significantly from expectations described in the forward-looking statements. For a discussion of such factors, please see Berkshire’s most recent reports on Forms 10-K and 10-Q filed with the Securities and Exchange Commission and available on the SEC’s website at www.sec.gov.  Berkshire does not undertake any obligation to update forward-looking statements.

NON-GAAP FINANCIAL MEASURES

This document contains certain non-GAAP financial measures in addition to results presented in accordance with Generally Accepted Accounting Principles (“GAAP”).  These non-GAAP measures provide supplemental perspectives on operating results, performance trends, and financial condition.  They are not a substitute for GAAP measures; they should be read and used in conjunction with the Company’s GAAP financial information.  A reconciliation of non-GAAP financial measures to GAAP

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measures is included in the accompanying financial tables.  In all cases, it should be understood that non-GAAP per share measures do not depict amounts that accrue directly to the benefit of shareholders.  The Company utilizes the non-GAAP measure of core earnings in evaluating operating trends, including components for core revenue and expense.  These measures exclude amounts which the Company views as unrelated to its normalized operations, including securities gains/losses, losses recorded for hedge terminations, merger costs, restructuring costs, systems conversion costs, and out-of-period adjustments.  Non-core adjustments are presented net of an adjustment for income tax expense.  This adjustment in 2013 was based on the marginal tax rate applied to the net non-core pre-tax adjustments.  In 2014, due to the comparative magnitude of the non-core items, this adjustment was determined as the difference between the GAAP tax rate and the effective tax rate applicable to core income.  Accordingly, GAAP net income exceeded core income in the two most recent quarters due to the higher effective full year tax rate on core income before the net non-core charges.  The efficiency ratio is adjusted for non-core revenue and expense items and for tax preference items.  The Company also calculates measures related to tangible equity, which adjust equity (and assets where applicable) to exclude intangible assets due to the importance of these measures to the investment community.  Charges related to merger and acquisition activity consist primarily of severance/benefit related expenses, contract termination costs, and professional fees.  Systems conversion costs relate primarily to the Company’s core systems conversion and related systems conversions costs.   Restructuring costs primarily consist of employee severance costs, as well as costs and losses associated with the disposition of assets which were undertaken as a project to right-size expenses following a decline in revenue in 2013.  Out-of-period accounting adjustments for interest income on acquired loans were recorded following systems conversions and merger related accounting activity and were deemed non-core.  Other non-core expenses include variable rate compensation related to non-core items as well as expenses related to the Bank’s charter change.

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CONTACTS

Investor Relations Contact

Allison O’Rourke, Vice President - Investor Relations; 413-236-3149

Media Contact

Ray Smith, Assistant Vice President - Marketing; 413-236-3756

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BERKSHIRE HILLS BANCORP, INC.

CONSOLIDATED BALANCE SHEETS - UNAUDITED - (F-1)

(1) The Company acquired 20 branches in Central New York on January 17, 2014, including $440 million in deposits and $4 million in loans.

F-1

BERKSHIRE HILLS BANCORP, INC.

CONSOLIDATED LOAN & DEPOSIT ANALYSIS - UNAUDITED - (F-2)

LOAN ANALYSIS

DEPOSIT ANALYSIS

(1) The Company acquired 20 branches in Central New York on January 17, 2014, including $440 million in deposits, as shown above, and $4 million in loans. Following the branch acquisition, year to date deposit growth is not annualized.

F-2

BERKSHIRE HILLS BANCORP, INC.

CONSOLIDATED STATEMENTS OF INCOME - UNAUDITED - (F-3)

(1) The Company acquired 20 branches in Central New York on January 17, 2014. The income statement for the three months ended March 31, 2014 includes operations of the branch acquisition beginning on that date.

(2) Merger, restructuring and conversion expenses include branch acquisition related expenses and bank charter change related expenses.

F-3

BERKSHIRE HILLS BANCORP, INC.

CONSOLIDATED STATEMENTS OF OPERATIONS - UNAUDITED - (F-4)

(1) See notes on Page F-3

F-4

BERKSHIRE HILLS BANCORP, INC.

ASSET QUALITY ANALYSIS - UNAUDITED - (F-5)