X0306 4 2020-01-31 0 0001108134 BERKSHIRE HILLS BANCORP INC BHLB 0001719481 Massad Pamela 24 NORTH STREET PITTSFIELD MA 01201 1 0 0 0 Common Stock 2020-01-31 5 W 0 1000000 0.00 D 3278744 I By Estate Common Stock 2020-01-31 5 W 0 1000000 0.00 A 1078369 D Common Stock 2020-02-10 5 W 0 2000000 0.00 D 1278744 I By Estate Common Stock 310 I By Stock Award I Common Stock 1075 I By Stock Award II Common Stock 1719 I By Stock Award III Series B Non-Voting Preferred Stock 260907 I By Estate Shares were distributed to the other beneficiaries of the Estate of David G. Massad, Sr. Stock Awards granted pursuant to the Berkshire Hills Bancorp, Inc. 2013 Equity Compensation Plan vest in three equal annual installments beginning on January 30, 2019. Stock Awards granted pursuant to the Berkshire Hills Bancorp, Inc. 2013 Equity Compensation Plan vest in three equal annual installments beginning on January 30, 2020. Stock Awards granted pursuant to the Berkshire Hills Bancorp, Inc. 2018 Equity Compensation Plan vest in three equal annual installments beginning on January 30, 2021. The Series B Non-Voting Preferred Stock may only be converted into Common Stock or disposed of by the Reporting Person under certain limited circumstances set forth in the Amended and Restated Shareholder Agreement attached to the Reporting Person's Schedule 13-D/A filed on January 22, 2020, and does not carry any voting rights. /s/ Marc Levy, pursuant to Power of Attorney 2020-02-12