| Kathleen Portolano | Accommodation and Food Services | $20,506 | $20,728 | 4 | <$5M |  AI Deep Dive |
| Oldcastle Productions INC | Arts, Entertainment, and Recreation | $20,075 | $20,176 | 5 | N/A | AI Deep Dive |
| Take Two Inc. | Information | $20,000 | $20,198 | 5 | <$5M | AI Deep Dive |
| Steven Wohlleber | Wholesale Trade | $19,886 | $0 | 1 | <$5M | AI Deep Dive |
| Amidon & Associates, INC | Finance and Insurance | $19,700 | $19,815 | 2 | <$5M | AI Deep Dive |
| Autowerks Paint & Collision LLC | Other Services (except Public Administration) | $19,097 | $19,194 | 1 | <$5M | AI Deep Dive |
| Njtl of Bennington Vt INC | Health Care and Social Assistance | $19,048 | $19,230 | 2 | N/A | AI Deep Dive |
| The Tuscan Sunflower LLC | Retail Trade | $19,017 | $19,166 | 3 | <$5M | AI Deep Dive |
| Bringing You to Vermont LLC | Retail Trade | $19,000 | $19,258 | 10 | <$5M | AI Deep Dive |
| Njtl of Bennington Vt INC | Health Care and Social Assistance | $19,000 | $19,276 | 21 | N/A | AI Deep Dive |
| K and L Associates, INC | Unknown | $18,750 | $18,926 | 2 | N/A | AI Deep Dive |
| Amidon & Associates INC | Finance and Insurance | $18,615 | $18,686 | 1 | <$5M | AI Deep Dive |
| Tony Bolio | Construction | $18,165 | $18,240 | 1 | <$5M | AI Deep Dive |
| Joseph Solari | Construction | $18,100 | $18,211 | 1 | <$5M | AI Deep Dive |
| Joseph a Solari | Construction | $18,100 | $18,301 | 1 | <$5M | AI Deep Dive |
| Jeffrey Magnifico | Accommodation and Food Services | $18,081 | $18,184 | 9 | <$5M | AI Deep Dive |
| Green Mountan Ingenuity LLC | Real Estate and Rental and Leasing | $17,900 | $18,044 | 6 | <$5M | AI Deep Dive |
| Jessica Gulley-Ward | Professional, Scientific, and Technical Services | $17,843 | $17,887 | 1 | <$5M | AI Deep Dive |
| Jonathan M Cohen | Professional, Scientific, and Technical Services | $17,700 | $17,819 | 2 | <$5M | AI Deep Dive |
| Windy Britches LLC | Accommodation and Food Services | $17,600 | $17,738 | 3 | <$5M | AI Deep Dive |
| Green Mountan Ingenuity LLC | Real Estate and Rental and Leasing | $16,909 | $17,029 | 6 | <$5M | AI Deep Dive |
| S & L Enterprises LLC | Retail Trade | $16,700 | $16,909 | 4 | <$5M | AI Deep Dive |
| Aaron Gilbert Building & Renovations LLC | Construction | $16,600 | $16,803 | 2 | <$5M | AI Deep Dive |
| Bennington County Association Against Child Abuse | Health Care and Social Assistance | $16,393 | $16,548 | 2 | N/A | AI Deep Dive |
| Better Bennington Corporation | Other Services (except Public Administration) | $16,100 | $16,336 | 3 | N/A | AI Deep Dive |