| Chesapeake Bay Maritime Museum INC | Arts, Entertainment, and Recreation | $687,500 | $692,637 | 59 | N/A |  AI Deep Dive |
| The Crab Claw INC | Accommodation and Food Services | $391,142 | $394,464 | 30 | $5.3M | AI Deep Dive |
| Madison Enterprises LLC | Accommodation and Food Services | $308,686 | $311,393 | 98 | $17.4M | AI Deep Dive |
| Joe Trippi and Associates INC | Professional, Scientific, and Technical Services | $278,600 | $281,812 | 13 | <$5M | AI Deep Dive |
| Limoncello of St. Michaels LLC | Accommodation and Food Services | $198,379 | $202,857 | 20 | <$5M | AI Deep Dive |
| Carpenter Street INC | Accommodation and Food Services | $148,511 | $150,053 | 28 | <$5M | AI Deep Dive |
| Shaws Incorporated | Construction | $145,797 | $146,324 | 11 | <$5M | AI Deep Dive |
| Clark and Cummings LLC | Accommodation and Food Services | $145,698 | $146,412 | 15 | <$5M | AI Deep Dive |
| Limoncello of St. Michaels, LLC | Accommodation and Food Services | $142,032 | $144,052 | 21 | <$5M | AI Deep Dive |
| Kckr Holding Co INC | Other Services (except Public Administration) | $72,165 | $72,987 | 8 | <$5M | AI Deep Dive |
| Slept Here Ltd | Accommodation and Food Services | $70,399 | $70,735 | 7 | <$5M | AI Deep Dive |
| St. Michaels Fine Woodworking and Cabinetry, LLC | Construction | $62,900 | $18,333 | 6 | <$5M | AI Deep Dive |
| Destination Lodging LLC | Accommodation and Food Services | $56,941 | $57,287 | 5 | <$5M | AI Deep Dive |
| Ejd Inc. | Retail Trade | $50,335 | $50,568 | 7 | <$5M | AI Deep Dive |
| Gourmet by the Bay LLC | Retail Trade | $38,040 | $38,203 | 5 | <$5M | AI Deep Dive |
| Rise Up St. Michaels LLC | Accommodation and Food Services | $37,249 | $37,390 | 9 | <$5M | AI Deep Dive |
| Balanced Care Physical Therapy LLC | Health Care and Social Assistance | $34,712 | $34,886 | 3 | <$5M | AI Deep Dive |
| Pascale Bernasse & Co INC | Administrative and Support and Waste Management | $27,560 | $27,657 | 2 | <$5M | AI Deep Dive |
| Charisma Clothing Boutique LLC | Retail Trade | $23,163 | $23,267 | 8 | <$5M | AI Deep Dive |
| Chris Handy Real Estate LLC | Real Estate and Rental and Leasing | $20,833 | $20,965 | 1 | <$5M | AI Deep Dive |
| Ellis J. Juan Consulting Services LLC | Professional, Scientific, and Technical Services | $20,800 | $21,051 | 1 | <$5M | AI Deep Dive |
| Kimberley Fritts | Professional, Scientific, and Technical Services | $20,246 | $0 | 1 | <$5M | AI Deep Dive |
| Price's Yacht Canvas, Inc. | Manufacturing | $20,190 | $20,267 | 7 | <$5M | AI Deep Dive |
| The Galley Restaurant, LLC | Accommodation and Food Services | $19,900 | $16,516 | 12 | <$5M | AI Deep Dive |
| Parsonage Associates | Accommodation and Food Services | $16,019 | $16,102 | 6 | <$5M | AI Deep Dive |