| $350,000–1 million | O'CONNELL OIL ASSOCIATES, INC. | PITTSFIELD, MA | Westfield Bank |
| $150,000–350,000 | OMAI, INC. | PITTSFIELD, MA | Adams Community Bank |
| $350,000–1 million | PEDIATRIC DEVELOPMENT CENTER INC | PITTSFIELD, MA | Greylock FCU |
| $150,000–350,000 | PEN-RO MOLD AND TOOL INC | PITTSFIELD, MA | Greylock FCU |
| $2–5 million | PETRICCA INDUSTRIES, INC. | PITTSFIELD, MA | TD Bank, National Association |
| $150,000–350,000 | PITTSFIELD LAWN & TRACTOR, INC. | PITTSFIELD, MA | MountainOne Bank |
| $350,000–1 million | PITTSFIELD MOTORS INC | PITTSFIELD, MA | Berkshire Bank |
| $150,000–350,000 | PITTSFIELD NEWS CO., INC. | PITTSFIELD, MA | Berkshire Bank |
| $350,000–1 million | PITTSFIELD PIPERS, INC | PITTSFIELD, MA | Customers Bank |
| $1–2 million | PITTSFIELD PLASTICS ENGR. LLC. | PITTSFIELD, MA | The Pittsfield Co-Operative Bank |
| $350,000–1 million | PITTSFIELD VETERINARY HOSPITAL | PITTSFIELD, MA | Berkshire Bank |
| $150,000–350,000 | RJM ANGELS LLC | PITTSFIELD, MA | Citizens Bank, National Association |
| $150,000–350,000 | ROBATEL INC | PITTSFIELD, MA | Berkshire Bank |
| $150,000–350,000 | RONNIE'S CYCLE SALES OF PITTSFIELD, INC. | PITTSFIELD, MA | Berkshire Bank |
| $150,000–350,000 | ROZ100 INC | PITTSFIELD, MA | TD Bank, National Association |
| $150,000–350,000 | RYAN ELECTRIC, INC. | PITTSFIELD, MA | The Pittsfield Co-Operative Bank |
| $150,000–350,000 | SALCO CONSTRUCTION COMPANY, INC. | PITTSFIELD, MA | The Pittsfield Co-Operative Bank |
| $350,000–1 million | SAMPCO INC. | PITTSFIELD, MA | Berkshire Bank |
| $150,000–350,000 | SK DESIGN GROUP INC | PITTSFIELD, MA | The Pittsfield Co-Operative Bank |
| $350,000–1 million | SMITH, WATSON & COMPANY, LLP | PITTSFIELD, MA | Greylock FCU |
| $1–2 million | SOLDIER ON INC | PITTSFIELD, MA | Berkshire Bank |
| $150,000–350,000 | SOLDIER ON OF DELAWARE INC. | PITTSFIELD, MA | Berkshire Bank |
| $150,000–350,000 | SOLEIL PERSONNEL INC | PITTSFIELD, MA | TD Bank, National Association |
| $350,000–1 million | STARBASE TECHNOLOGIES INC. | PITTSFIELD, MA | Berkshire Bank |
| $350,000–1 million | T & C FLYNNS PHARMACY INC | PITTSFIELD, MA | Berkshire Bank |
| $150,000–350,000 | TETON MANAGEMENT | PITTSFIELD, MA | Lee Bank |
| $2–5 million | THE BRIEN CENTER FOR MENTAL HEALTH AND SUBSTANCE ABUSE SERVICES, INC. | PITTSFIELD, MA | Berkshire Bank |
| $350,000–1 million | THE JOHNSON DEALERSHIPS, INC. | PITTSFIELD, MA | Greylock FCU |
| $350,000–1 million | TRANSPORTING THE PEOPLE, INC. | PITTSFIELD, MA | The Pittsfield Co-Operative Bank |
| $150,000–350,000 | TRUSTEES OF BERKSHIRE MUSEUM | PITTSFIELD, MA | Greylock FCU |
| $350,000–1 million | UCP OF WESTERN MASSACHUSETTS, INC | PITTSFIELD, MA | Greylock FCU |
| $150,000–350,000 | UNION LUNCH, INC. | PITTSFIELD, MA | Greylock FCU |
| $150,000–350,000 | WOHRLES FOODS INC | PITTSFIELD, MA | Greylock FCU |
| $150,000–350,000 | YARMOSKY PEDIATRIC DENTISTRY PC | PITTSFIELD, MA | Berkshire Bank |