| First Congregational Church of Bennington | Other Services (except Public Administration) | $23,600 | $23,749 | 5 | N/A |  AI Deep Dive |
| Forester Extraordinaire LLC | Agriculture, Forestry, Fishing and Hunting | $23,370 | $23,568 | 1 | <$5M | AI Deep Dive |
| Simmons Financial Partners LLC | Finance and Insurance | $22,900 | $23,035 | 3 | <$5M | AI Deep Dive |
| Bennington County Post #1332 Veterans of Foreign Wars of US | Other Services (except Public Administration) | $22,800 | $23,044 | 12 | N/A | AI Deep Dive |
| Cutler Electric LLC | Construction | $22,785 | $22,894 | 3 | <$5M | AI Deep Dive |
| Bennington Lodge No. 567 Benevolent and Protective Order of | Other Services (except Public Administration) | $22,769 | $22,940 | 25 | <$5M | AI Deep Dive |
| Bennington Tennis Center LLC | Arts, Entertainment, and Recreation | $22,747 | $22,966 | 2 | <$5M | AI Deep Dive |
| Oldcastle Productions INC | Arts, Entertainment, and Recreation | $22,188 | $22,261 | 6 | N/A | AI Deep Dive |
| All American Waste LLC | Administrative and Support and Waste Management | $21,837 | $21,958 | 2 | <$5M | AI Deep Dive |
| Growing Up Right at the C.d.c., Inc. | Health Care and Social Assistance | $21,600 | $21,790 | 4 | <$5M | AI Deep Dive |
| Bennington Tennis Center LLC | Arts, Entertainment, and Recreation | $21,250 | $21,562 | 2 | <$5M | AI Deep Dive |
| Tac LLC | Retail Trade | $20,900 | $21,027 | 5 | <$5M | AI Deep Dive |
| Bennington County Post #1332 Veterans of Foreign Wars of US | Other Services (except Public Administration) | $20,856 | $20,983 | 12 | N/A | AI Deep Dive |
| Babsons Contracting N Tree Care LLC | Construction | $20,833 | $20,947 | 1 | <$5M | AI Deep Dive |
| Joyce Gardner | Construction | $20,833 | $0 | 1 | <$5M | AI Deep Dive |
| Little Blue Deer | Professional, Scientific, and Technical Services | $20,833 | $20,916 | 1 | <$5M | AI Deep Dive |
| Michelle Pekrol | Retail Trade | $20,833 | $20,925 | 1 | <$5M | AI Deep Dive |
| Red Oak Ventures LLC | Retail Trade | $20,833 | $21,042 | 1 | <$5M | AI Deep Dive |
| Kirit G Patel | Accommodation and Food Services | $20,833 | $20,992 | 1 | <$5M | AI Deep Dive |
| Gerald Wall | Retail Trade | $20,800 | $21,082 | 1 | <$5M | AI Deep Dive |
| D. E. Greenawalt, CPA | Professional, Scientific, and Technical Services | $20,800 | $20,965 | 1 | <$5M | AI Deep Dive |
| Breezy Hill Farm Feed and Supply LLC | Retail Trade | $20,778 | $21,005 | 2 | <$5M | AI Deep Dive |
| The Village Chocolate Shoppe INC | Retail Trade | $20,760 | $20,908 | 3 | <$5M | AI Deep Dive |
| The Village Chocolate Shoppe INC | Manufacturing | $20,760 | $20,928 | 3 | <$5M | AI Deep Dive |
| Bennington Lanes, Inc. | Arts, Entertainment, and Recreation | $20,700 | $20,988 | 1 | <$5M | AI Deep Dive |