| Ghi Sign Service INC | Construction | $27,033 | $27,177 | 5 | <$5M |  AI Deep Dive |
| James Casey and Sons P&h Contractors | Construction | $26,338 | $26,508 | 3 | <$5M | AI Deep Dive |
| New Canaan Cares | Health Care and Social Assistance | $26,200 | $26,428 | 3 | N/A | AI Deep Dive |
| Berkshire Electric LLC | Construction | $25,129 | $25,402 | 2 | <$5M | AI Deep Dive |
| Mark Ustico Plumbing & Heating, LLC | Construction | $24,700 | $24,903 | 2 | <$5M | AI Deep Dive |
| Berkshire Hills Design, LLC | Professional, Scientific, and Technical Services | $24,644 | $24,918 | 3 | <$5M | AI Deep Dive |
| Railway Cafe LLC | Accommodation and Food Services | $23,999 | $24,321 | 14 | <$5M | AI Deep Dive |
| Jason Marshall Painting LLC | Construction | $23,758 | $24,000 | 2 | <$5M | AI Deep Dive |
| North Canaan Congregational Church | Other Services (except Public Administration) | $22,356 | $8,222 | 4 | N/A | AI Deep Dive |
| Haven House LLC | Health Care and Social Assistance | $22,323 | $22,522 | 2 | <$5M | AI Deep Dive |
| Dennis Kobylarz MD PC | Health Care and Social Assistance | $20,900 | $21,090 | 2 | <$5M | AI Deep Dive |
| Salvatore C Caruso | Finance and Insurance | $20,833 | $20,934 | 1 | <$5M | AI Deep Dive |
| Considine Construction LLC | Construction | $20,833 | $21,019 | 1 | <$5M | AI Deep Dive |
| Jason A. Lemon | Construction | $20,833 | $21,100 | 1 | <$5M | AI Deep Dive |
| Laurie Twing | Accommodation and Food Services | $20,833 | $0 | 1 | <$5M | AI Deep Dive |
| Salvatore C Caruso | Real Estate and Rental and Leasing | $20,833 | $21,017 | 1 | <$5M | AI Deep Dive |
| Considine Construction LLC | Construction | $20,832 | $21,054 | 1 | <$5M | AI Deep Dive |
| Roll-Flex, LLC | Manufacturing | $20,800 | $20,928 | 1 | <$5M | AI Deep Dive |
| Luke G Delabruere DBA Custom Design | Administrative and Support and Waste Management | $20,426 | $20,526 | 2 | <$5M | AI Deep Dive |
| Ghi Sign Service INC | Administrative and Support and Waste Management | $19,943 | $20,065 | 5 | <$5M | AI Deep Dive |
| Dylan Vadney DBA Vadneys Landscaping | Administrative and Support and Waste Management | $19,890 | $20,055 | 3 | <$5M | AI Deep Dive |
| Pop's Diner LLC Scott Simko | Accommodation and Food Services | $19,890 | $20,051 | 3 | <$5M | AI Deep Dive |
| Scott Andrews | Administrative and Support and Waste Management | $19,675 | $19,811 | 1 | <$5M | AI Deep Dive |
| R Foley Electric LLC | Construction | $18,162 | $18,286 | 1 | <$5M | AI Deep Dive |
| Thomas King | Manufacturing | $17,345 | $17,451 | 2 | <$5M | AI Deep Dive |