| Ann Marie Michaels Bookkeeping Services | Professional, Scientific, and Technical Services | $19,000 | $19,102 | 3 | <$5M | AI Deep Dive |
| Highbury House LLC | Professional, Scientific, and Technical Services | $18,750 | $18,849 | 1 | <$5M | AI Deep Dive |
| M & M Plus Enterprises | Accommodation and Food Services | $18,569 | $18,687 | 11 | <$5M | AI Deep Dive |
| Blair Benjamin | Unknown | $17,890 | $18,098 | 1 | N/A | AI Deep Dive |
| Paradise Farm Corporation | Agriculture, Forestry, Fishing and Hunting | $17,750 | $17,857 | 3 | <$5M | AI Deep Dive |
| Ann Marie Carlough | Professional, Scientific, and Technical Services | $17,629 | $17,750 | 2 | <$5M | AI Deep Dive |
| Room X Room LLC | Professional, Scientific, and Technical Services | $17,333 | $17,466 | 2 | <$5M | AI Deep Dive |
| Williamstown Hospitality LLC | Accommodation and Food Services | $17,300 | $17,475 | 5 | <$5M | AI Deep Dive |
| Greylock Gallery LLC | Unknown | $17,251 | $17,530 | 1 | N/A | AI Deep Dive |
| Steven Haskins | Construction | $17,095 | $17,286 | 2 | <$5M | AI Deep Dive |
| Steven Haskins DBA Haskins Construction | Construction | $17,094 | $17,243 | 4 | <$5M | AI Deep Dive |
| Alton & Westall Real Estate Agency, LLC | Real Estate and Rental and Leasing | $17,063 | $17,160 | 3 | <$5M | AI Deep Dive |
| James Turgeon | Construction | $16,763 | $16,826 | 1 | <$5M | AI Deep Dive |
| James E. Turgeon General Contractor | Construction | $16,762 | $16,825 | 1 | <$5M | AI Deep Dive |
| M. Ostrander LLC | Construction | $16,705 | $16,812 | 3 | <$5M | AI Deep Dive |
| M. Ostrander LLC | Professional, Scientific, and Technical Services | $16,072 | $16,264 | 2 | <$5M | AI Deep Dive |
| Room X Room, LLC | Professional, Scientific, and Technical Services | $16,000 | $16,086 | 2 | <$5M | AI Deep Dive |
| Laplante Appliance Service Center | Construction | $15,900 | $16,104 | 1 | <$5M | AI Deep Dive |
| George Stevens Construction INC | Construction | $15,720 | $15,863 | 2 | <$5M | AI Deep Dive |
| Berkshire Fitness Company of Williamstown, LLC | Arts, Entertainment, and Recreation | $15,700 | $15,823 | 1 | <$5M | AI Deep Dive |
| Livingstone Speed Academy LLC | Arts, Entertainment, and Recreation | $15,552 | $15,625 | 1 | <$5M | AI Deep Dive |
| Jeffrey Young | Agriculture, Forestry, Fishing and Hunting | $15,512 | $15,593 | 1 | <$5M | AI Deep Dive |
| Jeffrey Young | Agriculture, Forestry, Fishing and Hunting | $15,512 | $15,597 | 1 | <$5M | AI Deep Dive |
| The Cottage of Williamstown INC | Retail Trade | $15,319 | $15,482 | 2 | <$5M | AI Deep Dive |
| Thomas Derek Hargreaves | Administrative and Support and Waste Management | $15,000 | $15,069 | 1 | <$5M | AI Deep Dive |