| Michael Crawford | Wholesale Trade | $6,310 | $6,380 | 1 | <$5M |  AI Deep Dive |
| The Gamers Grotto LLC | Retail Trade | $6,300 | $6,344 | 3 | <$5M | AI Deep Dive |
| Lisa J. Carton, Licsw | Other Services (except Public Administration) | $6,250 | $6,286 | 1 | <$5M | AI Deep Dive |
| Institute of Medical Humanism, Inc. the | Educational Services | $6,250 | $6,319 | 2 | N/A | AI Deep Dive |
| Jennifer Rose | Health Care and Social Assistance | $6,250 | $6,284 | 1 | <$5M | AI Deep Dive |
| Handsome Hound, Inc. the | Other Services (except Public Administration) | $6,212 | $6,288 | 2 | <$5M | AI Deep Dive |
| Katherine Whitehall | Professional, Scientific, and Technical Services | $6,100 | $6,119 | 1 | <$5M | AI Deep Dive |
| Peter Radocchia | Unknown | $6,022 | $6,095 | 1 | N/A | AI Deep Dive |
| Papa Petes Restaurant of Bennington Vt-Sba Small 7a Term | Accommodation and Food Services | $5,990 | $3,637 | 4 | <$5M | AI Deep Dive |
| Green Mountain Landscape & Snow Removal INC | Administrative and Support and Waste Management | $5,900 | $5,929 | 2 | <$5M | AI Deep Dive |
| Rj Vosburgh | Other Services (except Public Administration) | $5,729 | $5,748 | 1 | <$5M | AI Deep Dive |
| Casandra P Guetti | Health Care and Social Assistance | $5,722 | $5,741 | 1 | <$5M | AI Deep Dive |
| Jaybern INC | Other Services (except Public Administration) | $5,700 | $5,725 | 1 | <$5M | AI Deep Dive |
| Nancy Hurley | Professional, Scientific, and Technical Services | $5,518 | $5,553 | 1 | <$5M | AI Deep Dive |
| Hobson Appliance LLC | Other Services (except Public Administration) | $5,300 | $5,370 | 1 | <$5M | AI Deep Dive |
| The American Legion Bennington Post #13 | Other Services (except Public Administration) | $5,213 | $5,269 | 5 | N/A | AI Deep Dive |
| Hairscapes INC | Other Services (except Public Administration) | $5,200 | $5,232 | 1 | <$5M | AI Deep Dive |
| Green Mountain Landscape & Snow Removal INC | Administrative and Support and Waste Management | $5,200 | $5,240 | 3 | <$5M | AI Deep Dive |
| Patel Investments INC | Accommodation and Food Services | $5,200 | $5,234 | 1 | <$5M | AI Deep Dive |
| Jay Z. Inc. | Retail Trade | $5,175 | $5,243 | 1 | <$5M | AI Deep Dive |
| Jay Z. Inc. | Retail Trade | $5,175 | $5,243 | 1 | <$5M | AI Deep Dive |
| Mattison Accounting LLC | Other Services (except Public Administration) | $5,022 | $5,077 | 1 | <$5M | AI Deep Dive |
| Lisa Carton | Health Care and Social Assistance | $5,000 | $5,019 | 1 | <$5M | AI Deep Dive |
| Frozen Solutions USA LLC Leapn Cow Cafe | Manufacturing | $4,495 | $4,516 | 3 | <$5M | AI Deep Dive |
| Massage Therapist | Health Care and Social Assistance | $4,460 | $4,490 | 1 | <$5M | AI Deep Dive |