| Pittsfield News Co., Inc. | Wholesale Trade | $305,700 | $309,360 | 45 | $11.6M |  AI Deep Dive |
| Trustees of Berkshire Museum | Arts, Entertainment, and Recreation | $305,500 | $307,851 | 28 | <$5M | AI Deep Dive |
| Boys and Girls Club of the Berkshires I | Health Care and Social Assistance | $295,360 | $296,968 | 37 | N/A | AI Deep Dive |
| Boys & Girls Club of the Berkshires INC | Other Services (except Public Administration) | $295,360 | $297,296 | 39 | N/A | AI Deep Dive |
| Mtm Dining, Inc. | Accommodation and Food Services | $292,100 | $295,978 | 40 | $7.1M | AI Deep Dive |
| Wohrles Foods INC | Wholesale Trade | $290,000 | $292,014 | 29 | $7.5M | AI Deep Dive |
| Berkshire Hospitality Group | Accommodation and Food Services | $289,020 | $292,785 | 25 | $7.8M | AI Deep Dive |
| Gigliotti Electric | Construction | $280,355 | $282,045 | 12 | <$5M | AI Deep Dive |
| M & W Heating, Inc. | Construction | $280,046 | $283,215 | 7 | $8.0M | AI Deep Dive |
| Eat Drink Inc. | Accommodation and Food Services | $278,124 | $280,890 | 18 | <$5M | AI Deep Dive |
| Yarmosky Pediatric Dentistry PC | Health Care and Social Assistance | $274,400 | $277,851 | 28 | $6.5M | AI Deep Dive |
| Berkshire Plastic Surgeons, LLC | Health Care and Social Assistance | $274,007 | $275,688 | 19 | $6.0M | AI Deep Dive |
| Advanced Berkshire Medical Imaging, PC | Health Care and Social Assistance | $272,700 | $275,836 | 12 | <$5M | AI Deep Dive |
| Barrington Stage Company, INC | Arts, Entertainment, and Recreation | $270,900 | $262,909 | 23 | N/A | AI Deep Dive |
| Yarmosky Pediatric Dentistry PC | Health Care and Social Assistance | $269,485 | $271,648 | 24 | $5.6M | AI Deep Dive |
| Gladys Allen Brigham Community Center, Inc. | Health Care and Social Assistance | $268,400 | $271,297 | 35 | N/A | AI Deep Dive |
| Omai, Inc. | Construction | $268,100 | $269,604 | 15 | <$5M | AI Deep Dive |
| Hotel On North, LLC | Accommodation and Food Services | $259,165 | $261,963 | 5 | <$5M | AI Deep Dive |
| Adelson & Company PC | Professional, Scientific, and Technical Services | $256,200 | $249,195 | 19 | $6.0M | AI Deep Dive |
| Berkshire Ear, Nose, Throat and Audiological Associates PC | Health Care and Social Assistance | $253,100 | $255,007 | 23 | $7.2M | AI Deep Dive |
| Crescent Creamery INC | Wholesale Trade | $253,000 | $255,176 | 22 | $5.7M | AI Deep Dive |
| Berkshire Community Action Council, Inc. | Health Care and Social Assistance | $248,110 | $251,957 | 28 | N/A | AI Deep Dive |
| Cantarella & Son, Inc. | Construction | $242,000 | $243,324 | 16 | <$5M | AI Deep Dive |
| M & W Heating Inc. | Construction | $240,635 | $241,973 | 9 | $10.3M | AI Deep Dive |
| Foresight Land Services, Inc. | Professional, Scientific, and Technical Services | $236,500 | $238,522 | 17 | <$5M | AI Deep Dive |