| Peter K. Weik Custom Carpentry, LLC | Construction | $7,400 | $7,528 | 1 | <$5M |  AI Deep Dive |
| Outside Perspectives Inc. | Health Care and Social Assistance | $7,339 | $7,429 | 2 | N/A | AI Deep Dive |
| Morgan Weir Post #27 American Legion Memorial Home Inc. | Other Services (except Public Administration) | $6,900 | $6,934 | 4 | <$5M | AI Deep Dive |
| Rachel's Quality Consignment | Retail Trade | $6,875 | $6,905 | 1 | <$5M | AI Deep Dive |
| Jrl Associates LLC | Administrative and Support and Waste Management | $6,667 | $6,754 | 1 | <$5M | AI Deep Dive |
| Outside Perspectives, Inc. | Health Care and Social Assistance | $6,500 | $6,534 | 2 | N/A | AI Deep Dive |
| Scott Bennett | Construction | $6,243 | $6,324 | 1 | <$5M | AI Deep Dive |
| Milton Congregational Church | Other Services (except Public Administration) | $6,000 | $6,029 | 3 | N/A | AI Deep Dive |
| Drl Trading | Wholesale Trade | $5,657 | $5,716 | 1 | <$5M | AI Deep Dive |
| Drl Trading LLC | Wholesale Trade | $5,657 | $5,735 | 1 | <$5M | AI Deep Dive |
| David Vincenzi | Manufacturing | $5,459 | $5,491 | 1 | <$5M | AI Deep Dive |
| John K Bowling Jr | Accommodation and Food Services | $5,300 | $5,389 | 1 | <$5M | AI Deep Dive |
| Litchfield Tailor Shop LLC | Retail Trade | $5,236 | $10,822 | 1 | <$5M | AI Deep Dive |
| Fabric Studio LLC | Retail Trade | $5,100 | $5,152 | 1 | <$5M | AI Deep Dive |
| Bird Mentor | Agriculture, Forestry, Fishing and Hunting | $5,098 | $5,135 | 1 | <$5M | AI Deep Dive |
| Lily Deering | Retail Trade | $5,095 | $5,114 | 1 | <$5M | AI Deep Dive |
| PC Home Improvement LLC | Construction | $5,048 | $5,090 | 1 | <$5M | AI Deep Dive |
| Anne Marie Walsh and Papineau Studio | Professional, Scientific, and Technical Services | $4,900 | $4,942 | 1 | <$5M | AI Deep Dive |
| Methodist Church of Litchfield | Other Services (except Public Administration) | $4,800 | $4,846 | 1 | <$5M | AI Deep Dive |
| Lindsay Baker | Other Services (except Public Administration) | $4,567 | $0 | 1 | <$5M | AI Deep Dive |
| Happy Mama Happy Baby | Health Care and Social Assistance | $4,375 | $4,414 | 1 | <$5M | AI Deep Dive |
| Kawasaki Restaurant Corp | Accommodation and Food Services | $3,911 | $3,961 | 5 | <$5M | AI Deep Dive |
| Big Johnsons Guitars | Arts, Entertainment, and Recreation | $3,750 | $3,766 | 1 | <$5M | AI Deep Dive |
| Christine Decarolis | Health Care and Social Assistance | $3,640 | $3,668 | 1 | <$5M | AI Deep Dive |
| Papermoon Performing Arts, LLC | Educational Services | $3,475 | $3,519 | 1 | <$5M | AI Deep Dive |