| $350,000–1 million | 18 DEGREES, INC | PITTSFIELD, MA | Greylock FCU |
| $150,000–350,000 | ADELSON & COMPANY PC | PITTSFIELD, MA | Berkshire Bank |
| $150,000–350,000 | ADVANCED BERKSHIRE MEDICAL IMAGING, PC | PITTSFIELD, MA | Greylock FCU |
| $2–5 million | ADVANCED IMPACT TECHNOLOGIES GROUP INC | PITTSFIELD, MA | Truist Bank d/b/a Branch Banking & Trust Co |
| $150,000–350,000 | AER INC | PITTSFIELD, MA | Berkshire Bank |
| $150,000–350,000 | ANTERIS SOLUTIONS, INC. | PITTSFIELD, MA | Lee Bank |
| $150,000–350,000 | B&G RESTAURANT SUPPLY, INC. | PITTSFIELD, MA | Citizens Bank, National Association |
| $150,000–350,000 | BARRINGTON STAGE COMPANY, INC | PITTSFIELD, MA | Berkshire Bank |
| $150,000–350,000 | BERKSHIRE HOSPITALITY GROUP | PITTSFIELD, MA | TD Bank, National Association |
| $150,000–350,000 | BERKSHIRE ALLERGY CARE PC | PITTSFIELD, MA | St. Mary's CU |
| $150,000–350,000 | BERKSHIRE AUTO GROUP | PITTSFIELD, MA | Greylock FCU |
| $150,000–350,000 | BERKSHIRE COMMUNICATORS, INC. | PITTSFIELD, MA | Lee Bank |
| $150,000–350,000 | BERKSHIRE COMMUNITY ACTION COUNCIL, INC. | PITTSFIELD, MA | Kabbage, Inc. |
| $5–10 million | BERKSHIRE COUNTY ARC INC | PITTSFIELD, MA | Berkshire Bank |
| $350,000–1 million | BERKSHIRE COUNTY HEAD START CHILD DEVELOPMENT PROGRAM, INC. | PITTSFIELD, MA | Windsor Federal Savings & Loan Association |
| $150,000–350,000 | BERKSHIRE CUSTOM COATING, INC. | PITTSFIELD, MA | MountainOne Bank |
| $150,000–350,000 | BERKSHIRE EAR, NOSE, THROAT AND AUDIOLOGICAL ASSOCIATES PC | PITTSFIELD, MA | Berkshire Bank |
| $150,000–350,000 | BERKSHIRE ENVIRONMENTAL CONSULTANTS INC | PITTSFIELD, MA | Greylock FCU |
| $350,000–1 million | BERKSHIRE EYE CENTER | PITTSFIELD, MA | Berkshire Bank |
| $350,000–1 million | BERKSHIRE HOUSING SERVICES, INC. | PITTSFIELD, MA | The Pittsfield Co-Operative Bank |
| $150,000–350,000 | BERKSHIRE HUMANE SOCIETY, INC. | PITTSFIELD, MA | The Pittsfield Co-Operative Bank |
| $150,000–350,000 | BERKSHIRE PLASTIC SURGEONS, LLC | PITTSFIELD, MA | TD Bank, National Association |
| $350,000–1 million | BERKSHIRE PRECISION TOOL, LLC | PITTSFIELD, MA | Berkshire Bank |
| $150,000–350,000 | BERKSHIRE RENTALS, INC. | PITTSFIELD, MA | Lee Bank |
| $350,000–1 million | BERKSHIRE RETIREMENT HOME, INC. | PITTSFIELD, MA | Adams Community Bank |
| $150,000–350,000 | BERKSHIRE THEATRE GROUP INC | PITTSFIELD, MA | Lee Bank |
| $150,000–350,000 | BERKSHIRE TRAINING AND EMPLOYMENT, INC. | PITTSFIELD, MA | Adams Community Bank |
| $350,000–1 million | BERKSHIRE WIRELESS CORP. | PITTSFIELD, MA | Greylock FCU |
| $350,000–1 million | BERKSHIRE YOUNG MEN'S CHRISTIAN ASSOCIATION | PITTSFIELD, MA | MountainOne Bank |
| $350,000–1 million | BLUE Q CORPORATION | PITTSFIELD, MA | Greylock FCU |
| $150,000–350,000 | BOYS & GIRLS CLUB OF THE BERKSHIRES INC | PITTSFIELD, MA | TD Bank, National Association |
| $150,000–350,000 | BRAZEE & HUBAN CPAS | PITTSFIELD, MA | Adams Community Bank |
| $350,000–1 million | BRILLIANT GRAPHICS GROUP LLC | PITTSFIELD, MA | Bank of America, National Association |
| $150,000–350,000 | BUILDING BLOCKS EARLY EDUCATION CENTER, | PITTSFIELD, MA | Greylock FCU |
| $150,000–350,000 | C T MANAGEMENT GROUP, LLC | PITTSFIELD, MA | Berkshire Bank |
| $150,000–350,000 | CAIN, HIBBARD & MYERS, PC | PITTSFIELD, MA | Berkshire Bank |
| $150,000–350,000 | CAMPOLI MONTELEONE & MOZIAN PC | PITTSFIELD, MA | TD Bank, National Association |
| $150,000–350,000 | CANTARELLA & SON, INC. | PITTSFIELD, MA | The Pittsfield Co-Operative Bank |
| $350,000–1 million | CARR HARDWARE & SUPPLY CO INC | PITTSFIELD, MA | Berkshire Bank |
| $1–2 million | CAVALLERO PLASTICS, INC. | PITTSFIELD, MA | TD Bank, National Association |
| $350,000–1 million | CENTER FOR ECOTECHNOLOGY, INC. | PITTSFIELD, MA | Westfield Bank |
| $150,000–350,000 | CHAMPLAIN MASONRY, INC. | PITTSFIELD, MA | Berkshire Bank |
| $350,000–1 million | CLIMATE HEATING AND COOLING, INC. | PITTSFIELD, MA | Berkshire Bank |
| $350,000–1 million | COHEN, KINNE, VALICENTI AND COOK LLP | PITTSFIELD, MA | Greylock FCU |
| $1–2 million | COLLEGE INTERNSHIP PROGRAM, INC. | PITTSFIELD, MA | NBT Bank, National Association |
| $150,000–350,000 | COMALLI GROUP INC | PITTSFIELD, MA | Berkshire Bank |
| $1–2 million | COMMUNITY ECO POWER, LLC | PITTSFIELD, MA | Berkshire Bank |
| $350,000–1 million | COMPUWORKS LTD. | PITTSFIELD, MA | The Pittsfield Co-Operative Bank |
| $350,000–1 million | COUNTY AMBULANCE INC | PITTSFIELD, MA | Greylock FCU |
| $150,000–350,000 | COUNTY RAINBOW TAXI, INC | PITTSFIELD, MA | The Pittsfield Co-Operative Bank |
| $150,000–350,000 | COURTNEY, LEE & HAMEL, PC | PITTSFIELD, MA | The Pittsfield Co-Operative Bank |
| $150,000–350,000 | CRESCENT CREAMERY INC | PITTSFIELD, MA | Berkshire Bank |
| $350,000–1 million | DANIEL BURKE ELECTRICAL CONSULTING & INSTALLATIONS, INC. | PITTSFIELD, MA | The Pittsfield Co-Operative Bank |
| $350,000–1 million | DAVID J TIERNEY JR INC | PITTSFIELD, MA | Berkshire Bank |
| $150,000–350,000 | DBM RANCH,INC | PITTSFIELD, MA | MountainOne Bank |
| $150,000–350,000 | DETTINGER LUMBER COMPANY INC | PITTSFIELD, MA | Lee Bank |
| $350,000–1 million | DNS ENTERPRISES, LTD | PITTSFIELD, MA | Greylock FCU |
| $150,000–350,000 | DOWNTOWN NORTH INC | PITTSFIELD, MA | Greylock FCU |
| $150,000–350,000 | EAST ELM PEDIATRICS, LLC | PITTSFIELD, MA | The Pittsfield Co-Operative Bank |
| $150,000–350,000 | EAT DRINK, INC. | PITTSFIELD, MA | MountainOne Bank |
| $350,000–1 million | EDM SERVICES, INC. | PITTSFIELD, MA | Berkshire Bank |
| $150,000–350,000 | FORESIGHT LAND SERVICES, INC. | PITTSFIELD, MA | Berkshire Bank |
| $1–2 million | FRESH AMERICAN LLC | PITTSFIELD, MA | Rockland Trust Company |
| $350,000–1 million | GABLE ELECTRIC INC | PITTSFIELD, MA | Greylock FCU |
| $1–2 million | GAHCR II PITTSFIELD MA SNF TRS LLC | PITTSFIELD, MA | Manufacturers and Traders Trust Company |
| $150,000–350,000 | GAN SYSTEMS CORP. | PITTSFIELD, MA | City National Bank |
| $2–5 million | GEMI MANAGEMENT COMPANY INC | PITTSFIELD, MA | Greylock FCU |
| $150,000–350,000 | GIGLIOTTI ELECTRIC | PITTSFIELD, MA | MountainOne Bank |
| $150,000–350,000 | GLADYS ALLEN BRIGHAM COMMUNITY CENTER, INC. | PITTSFIELD, MA | The Pittsfield Co-Operative Bank |
| $350,000–1 million | GOODWILL OF THE BERKSHIRES AND SOUTHERN VERMONT, INC | PITTSFIELD, MA | MountainOne Bank |
| $150,000–350,000 | GRAPHIC IMPACT SIGNS INC. | PITTSFIELD, MA | Trustco Bank |
| $1–2 million | GUIDO'S FRESH MARKETPLACE | PITTSFIELD, MA | Greylock FCU |
| $350,000–1 million | GYMFEST OF THE BERKSHIRES, INC. | PITTSFIELD, MA | MountainOne Bank |
| $150,000–350,000 | HANCOCK SHAKER VILLAGE INC | PITTSFIELD, MA | Berkshire Bank |
| $150,000–350,000 | HGC INC. | PITTSFIELD, MA | Berkshire Bank |
| $1–2 million | HI-TECH MOLD & TOOL, INC. | PITTSFIELD, MA | TD Bank, National Association |
| $150,000–350,000 | HILLCREST DENTAL CARE INC | PITTSFIELD, MA | Greylock FCU |
| $150,000–350,000 | HOTEL ON NORTH, LLC | PITTSFIELD, MA | MountainOne Bank |
| $2–5 million | J.H. MAXYMILLIAN, INC. | PITTSFIELD, MA | Berkshire Bank |
| $150,000–350,000 | JOHN MAKUC DVM LLC DBA BERKSHIRE VETERINARY HOSPITAL | PITTSFIELD, MA | Berkshire Bank |
| $150,000–350,000 | KIDZONE CHILD CARE EDUCATIONAL CENTERS INC | PITTSFIELD, MA | MountainOne Bank |
| $350,000–1 million | LAURIN PUBLISHING CO., INC. | PITTSFIELD, MA | The Pittsfield Co-Operative Bank |
| $350,000–1 million | LIPTON INC | PITTSFIELD, MA | Berkshire Bank |
| $150,000–350,000 | LOMBARDI, CLAIRMONT & KEEGAN, CPA'S | PITTSFIELD, MA | Greylock FCU |
| $1–2 million | LYON AVIATION | PITTSFIELD, MA | Berkshire Bank |
| $150,000–350,000 | M & W HEATING, INC. | PITTSFIELD, MA | MountainOne Bank |
| $150,000–350,000 | MACFARLANE OFFICE PRODUCTS, INC | PITTSFIELD, MA | Berkshire Bank |
| $150,000–350,000 | MARTN & OLIVERIA, LLP | PITTSFIELD, MA | Lee Bank |
| $150,000–350,000 | MAZZEO'S OF GREAT BARRINGTON | PITTSFIELD, MA | Berkshire Bank |
| $150,000–350,000 | MICHAEL A. BIANCO LANDSCAPING, INC | PITTSFIELD, MA | Greylock FCU |
| $150,000–350,000 | MICHAEL RENZI PAINTING CO., LLC | PITTSFIELD, MA | Berkshire Bank |
| $1–2 million | MISS HALL'S SCHOOL, INC. | PITTSFIELD, MA | NBT Bank, National Association |
| $350,000–1 million | MODERN MOLD AND TOOL INC | PITTSFIELD, MA | TD Bank, National Association |
| $350,000–1 million | MOLARI INC | PITTSFIELD, MA | TD Bank, National Association |
| $350,000–1 million | MOUNTAIN VIEW HOME CARE. INC. | PITTSFIELD, MA | The Pittsfield Co-Operative Bank |
| $150,000–350,000 | MRM HOSPITALITY LLC | PITTSFIELD, MA | Lee Bank |
| $150,000–350,000 | MTM DINING, INC. | PITTSFIELD, MA | Greylock FCU |
| $350,000–1 million | MULLEN BROS INC OF NO ADAMS | PITTSFIELD, MA | TD Bank, National Association |
| $150,000–350,000 | NATALYA YANTOVSKY DMD PC | PITTSFIELD, MA | Berkshire Bank |
| $1–2 million | NEW ENGLAND NEWSPAPERS, INC. | PITTSFIELD, MA | MountainOne Bank |