| Taft Farms INC | Agriculture, Forestry, Fishing and Hunting | $103,700 | $105,132 | 34 | <$5M |  AI Deep Dive |
| Mahaiwe Tent INC | Other Services (except Public Administration) | $102,478 | $103,101 | 12 | <$5M | AI Deep Dive |
| I.e. Inc. | Accommodation and Food Services | $102,110 | $102,479 | 33 | $6.2M | AI Deep Dive |
| Tp Saddleblanket and Trading INC | Wholesale Trade | $101,175 | $102,320 | 11 | <$5M | AI Deep Dive |
| Hevreh of Southern Berkshire, Inc. | Other Services (except Public Administration) | $100,600 | $78,909 | 6 | N/A | AI Deep Dive |
| Public House INC | Accommodation and Food Services | $100,187 | $100,697 | 17 | <$5M | AI Deep Dive |
| Railroad Street Youth Project INC | Other Services (except Public Administration) | $99,577 | $100,033 | 15 | N/A | AI Deep Dive |
| Well-Kamp Enterprises, Inc. | Construction | $99,555 | $100,283 | 11 | <$5M | AI Deep Dive |
| Volunteers in Medicine Berkshires, Inc. | Health Care and Social Assistance | $98,000 | $89,946 | 16 | $5.0M | AI Deep Dive |
| Clark & Green, Inc. | Professional, Scientific, and Technical Services | $97,250 | $97,865 | 7 | <$5M | AI Deep Dive |
| Railroad Street Youth Project INC | Other Services (except Public Administration) | $95,600 | $96,216 | 16 | N/A | AI Deep Dive |
| Kwik Print, Inc. | Information | $95,200 | $70,791 | 6 | <$5M | AI Deep Dive |
| Carjac INC | Retail Trade | $94,787 | $95,240 | 18 | <$5M | AI Deep Dive |
| Berkshire Hills K&b LLC | Construction | $93,365 | $94,253 | 8 | <$5M | AI Deep Dive |
| The Orion Society, Inc. | Professional, Scientific, and Technical Services | $90,606 | $91,075 | 8 | N/A | AI Deep Dive |
| Micheles Salon and Day Spa INC | Other Services (except Public Administration) | $89,000 | $89,546 | 19 | <$5M | AI Deep Dive |
| Berkshire Hills K and B LLC | Retail Trade | $88,355 | $89,081 | 9 | <$5M | AI Deep Dive |
| Berkshire Aviation Enterprises, LLC | Transportation and Warehousing | $87,307 | $87,924 | 11 | <$5M | AI Deep Dive |
| Berkshire Aviation Enterprises LLC | Transportation and Warehousing | $87,307 | $87,907 | 11 | <$5M | AI Deep Dive |
| Construct, Inc. | Health Care and Social Assistance | $85,865 | $86,388 | 12 | <$5M | AI Deep Dive |
| Jonathan J Nacht PC | Health Care and Social Assistance | $85,000 | $85,543 | 8 | <$5M | AI Deep Dive |
| Fiddleheads Grille Inc. | Accommodation and Food Services | $84,522 | $85,559 | 7 | <$5M | AI Deep Dive |
| Xicohtencatl Mexican Restaurant, Inc. | Accommodation and Food Services | $84,000 | $84,651 | 32 | $5.7M | AI Deep Dive |
| Briggs Capital Management LLC | Other Services (except Public Administration) | $83,909 | $84,490 | 4 | <$5M | AI Deep Dive |
| Micheles Salon and Day Spa INC | Other Services (except Public Administration) | $83,902 | $0 | 15 | <$5M | AI Deep Dive |