| $350,000–1 million | BEAR MOUNTAIN 320 OPERATING, LLC | GREAT BARRINGTON, MA | CIBC Bank USA |
| $150,000–350,000 | BERKSHIRE BIKE, LLC | GREAT BARRINGTON, MA | Lee Bank |
| $350,000–1 million | BERKSHIRE COOPERATIVE ASSOCIATION, INC. | GREAT BARRINGTON, MA | The Pittsfield Co-Operative Bank |
| $1–2 million | BERKSHIRE CORPORATION | GREAT BARRINGTON, MA | NBT Bank, National Association |
| $150,000–350,000 | BERKSHIRE HOLDING CORPORATION | GREAT BARRINGTON, MA | NBT Bank, National Association |
| $150,000–350,000 | BERKSHIRE MOUNTAIN BREWERS INC | GREAT BARRINGTON, MA | Berkshire Bank |
| $150,000–350,000 | BERKSHIRE PROPERTY AGENTS | GREAT BARRINGTON, MA | Berkshire Bank |
| $150,000–350,000 | BERKSHIRE SOUTH REGIONAL COMMUNITY CENTER | GREAT BARRINGTON, MA | Berkshire Bank |
| $150,000–350,000 | BERKSHIRE WALDORF SCHOOL,INC | GREAT BARRINGTON, MA | NBT Bank, National Association |
| $150,000–350,000 | BUTTERNUT BASIN INC | GREAT BARRINGTON, MA | Lee Bank |
| $350,000–1 million | CATAMOUNT SKI RESORT LLC | GREAT BARRINGTON, MA | Salisbury Bank & Trust Company |
| $150,000–350,000 | COMMUNITY ACCESS TO THE ARTS, INC. | GREAT BARRINGTON, MA | Lee Bank |
| $2–5 million | COMMUNITY HEALTH PROGRAMS, INCORPORATED | GREAT BARRINGTON, MA | Salisbury Bank & Trust Company |
| $150,000–350,000 | E CALIGARI AND SON | GREAT BARRINGTON, MA | TD Bank, National Association |
| $150,000–350,000 | G A BLANCO & SONS, INC | GREAT BARRINGTON, MA | TD Bank, National Association |
| $150,000–350,000 | GENNARI PLUMBING & HEATING, INC | GREAT BARRINGTON, MA | Greylock FCU |
| $150,000–350,000 | J.P.C. POPS, INC. | GREAT BARRINGTON, MA | The Pittsfield Co-Operative Bank |
| $150,000–350,000 | JOHN B HULL INC | GREAT BARRINGTON, MA | Lee Bank |
| $350,000–1 million | LIFE NEEDS COOP INC. | GREAT BARRINGTON, MA | The Bank of Greene County |
| $150,000–350,000 | MAHAIWE PERFORMING ARTS CENTER, INC. | GREAT BARRINGTON, MA | Berkshire Bank |
| $150,000–350,000 | MONGIARDO STUDIO INC. | GREAT BARRINGTON, MA | Lee Bank |
| $150,000–350,000 | OLD INN ON THE GREEN, LLC | GREAT BARRINGTON, MA | Lee Bank |
| $150,000–350,000 | PETER FASANO,LTD LLC | GREAT BARRINGTON, MA | Lee Bank |
| $150,000–350,000 | S & A SUPPLY, INC. | GREAT BARRINGTON, MA | KeyBank National Association |
| $150,000–350,000 | SOUTHERN BERKSHIRE VOLUNTEER AMBULANCE SQUAD, INC | GREAT BARRINGTON, MA | Greylock FCU |
| $150,000–350,000 | THE CHAMBERLAIN GROUP, LLC | GREAT BARRINGTON, MA | Lee Bank |
| $150,000–350,000 | THE JOHN DEWEY ACADEMY INC | GREAT BARRINGTON, MA | TD Bank, National Association |
| $150,000–350,000 | WARD'S NURSERY | GREAT BARRINGTON, MA | Lee Bank |
| $350,000–1 million | WHEELER AND TAYLOR, INC. | GREAT BARRINGTON, MA | Salisbury Bank & Trust Company |
| $150,000–350,000 | WINDY HILL FARM INC. | GREAT BARRINGTON, MA | Berkshire Bank |
| $150,000–350,000 | WOOD ANCHOR RESTAURANT | GREAT BARRINGTON, MA | Salisbury Bank & Trust Company |