| Option Institute & Fellowship | Educational Services | $427,500 | $428,984 | 44 | $5.7M |  AI Deep Dive |
| The Option Institute & Fellowship | Other Services (except Public Administration) | $398,093 | $400,623 | 28 | $5.3M | AI Deep Dive |
| Berkshire Taconic Community Foundation, Inc. | Other Services (except Public Administration) | $378,900 | $381,879 | 19 | N/A | AI Deep Dive |
| The Great Barrington Marketplace INC | Accommodation and Food Services | $359,500 | $352,913 | 166 | $29.5M | AI Deep Dive |
| Sheffield Pottery, Inc. | Manufacturing | $343,200 | $346,735 | 27 | $26.8M | AI Deep Dive |
| Joe Wilkinson Excavating, Inc. | Construction | $246,138 | $247,547 | 26 | $9.7M | AI Deep Dive |
| Massini Bus Company INC | Transportation and Warehousing | $200,170 | $201,870 | 40 | $15.4M | AI Deep Dive |
| The Haupt Tree Company INC | Administrative and Support and Waste Management | $194,500 | $196,616 | 20 | <$5M | AI Deep Dive |
| Undermountain Hospitality LLC | Accommodation and Food Services | $174,891 | $177,555 | 20 | $6.3M | AI Deep Dive |
| Carlson Heating & Air Conditioning INC | Construction | $134,160 | $90,619 | 11 | <$5M | AI Deep Dive |
| Undermountain Hospitality LLC | Accommodation and Food Services | $132,540 | $134,116 | 25 | <$5M | AI Deep Dive |
| Aquatic Designs, Inc. | Construction | $125,261 | $126,390 | 14 | <$5M | AI Deep Dive |
| Gregg S Massini Bus Company INC | Transportation and Warehousing | $119,263 | $120,204 | 32 | $12.3M | AI Deep Dive |
| Webster-Ingersoll, Inc. | Professional, Scientific, and Technical Services | $118,874 | $119,965 | 6 | <$5M | AI Deep Dive |
| Nappi International USA INC | Health Care and Social Assistance | $110,000 | $111,043 | 8 | <$5M | AI Deep Dive |
| Pine Island Farm Partnership | Agriculture, Forestry, Fishing and Hunting | $109,493 | $110,789 | 13 | <$5M | AI Deep Dive |
| Rock Solid Marble & Granite LLC | Construction | $109,105 | $110,023 | 12 | <$5M | AI Deep Dive |
| Bachetti's Auto Sales, INC | Retail Trade | $99,400 | $100,248 | 9 | <$5M | AI Deep Dive |
| Rock Solid Marble and Granite LLC | Construction | $95,900 | $96,665 | 11 | <$5M | AI Deep Dive |
| Race Mountain Tree Services INC | Agriculture, Forestry, Fishing and Hunting | $92,896 | $93,336 | 8 | <$5M | AI Deep Dive |
| Race Mountain Tree Services INC | Agriculture, Forestry, Fishing and Hunting | $92,800 | $93,596 | 9 | <$5M | AI Deep Dive |
| Coalition for a Prosperous America Education Fund, Inc. | Educational Services | $88,345 | $88,839 | 4 | <$5M | AI Deep Dive |
| Coalition for a Prosperous America Education Fund Inc. | Other Services (except Public Administration) | $87,777 | $88,179 | 4 | <$5M | AI Deep Dive |
| Berkshire Gmc Inc. | Retail Trade | $86,500 | $87,378 | 8 | <$5M | AI Deep Dive |
| Wilkinson General Contracting INC | Construction | $82,000 | $82,577 | 8 | <$5M | AI Deep Dive |