| Toole Management Group, LLC | Professional, Scientific, and Technical Services | $35,540 | $35,807 | 3 | <$5M | AI Deep Dive |
| Toole Management Group LLC | Professional, Scientific, and Technical Services | $35,540 | $35,738 | 3 | <$5M | AI Deep Dive |
| The Frederick LLC | Accommodation and Food Services | $35,200 | $35,453 | 8 | <$5M | AI Deep Dive |
| Bagel & Brew LLC | Accommodation and Food Services | $34,500 | $34,799 | 5 | <$5M | AI Deep Dive |
| Shyamji.inc. | Accommodation and Food Services | $34,286 | $34,560 | 9 | <$5M | AI Deep Dive |
| Berkshire Psychodynamic Psychiatry, Inc. | Health Care and Social Assistance | $33,235 | $33,406 | 2 | <$5M | AI Deep Dive |
| Berkshire Institute for Christian Studies Inc. | Other Services (except Public Administration) | $32,911 | $33,036 | 7 | N/A | AI Deep Dive |
| Berkshire Institute for Christian Studies, Inc. | Educational Services | $32,900 | $33,043 | 7 | N/A | AI Deep Dive |
| Sam Kasten Handweaver LLC | Retail Trade | $32,400 | $32,741 | 4 | <$5M | AI Deep Dive |
| Lenox Cat Hospital, Inc. | Professional, Scientific, and Technical Services | $31,600 | $31,917 | 4 | <$5M | AI Deep Dive |
| Berkshire Lighting Outlet | Manufacturing | $31,100 | $31,539 | 3 | <$5M | AI Deep Dive |
| Purple Plume | Retail Trade | $30,500 | $30,762 | 5 | <$5M | AI Deep Dive |
| Stanley Rosen | Accommodation and Food Services | $30,345 | $30,516 | 2 | <$5M | AI Deep Dive |
| Karen Beckwith Art and Interiors | Professional, Scientific, and Technical Services | $29,900 | $30,165 | 2 | <$5M | AI Deep Dive |
| Twinkle Toes Inc. | Retail Trade | $29,874 | $30,002 | 4 | <$5M | AI Deep Dive |
| Greylock Design Associates Inc. | Professional, Scientific, and Technical Services | $29,750 | $30,188 | 3 | <$5M | AI Deep Dive |
| Twinkle Toes, INC | Retail Trade | $29,600 | $29,850 | 4 | <$5M | AI Deep Dive |
| Roman Catholic Bishop of Springfield a Corp Sole for St Ann | Other Services (except Public Administration) | $29,302 | $29,603 | 11 | N/A | AI Deep Dive |
| Roman Catholic Bishop of Springfield a Corp Sole for St Ann | Other Services (except Public Administration) | $29,300 | $29,534 | 5 | N/A | AI Deep Dive |
| Berkshire Coffee Roasting Co. of Lenox | Retail Trade | $29,200 | $29,488 | 7 | <$5M | AI Deep Dive |
| Lalji Inc. | Accommodation and Food Services | $28,857 | $29,084 | 7 | <$5M | AI Deep Dive |
| Cassandra Sohn Photography LLC | Retail Trade | $28,610 | $28,951 | 3 | <$5M | AI Deep Dive |
| Judith Culver | Retail Trade | $28,398 | $28,688 | 5 | <$5M | AI Deep Dive |
| Lee Goldstein | Retail Trade | $27,859 | $27,996 | 2 | <$5M | AI Deep Dive |
| Lee Goldstein | Retail Trade | $27,800 | $27,958 | 2 | <$5M | AI Deep Dive |