| Chesapeake Bay Maritime Museum INC | Arts, Entertainment, and Recreation | $687,500 | $692,733 | 59 | N/A |  AI Deep Dive |
| The Highland Consulting Group, Inc. | Professional, Scientific, and Technical Services | $627,500 | $472,476 | 42 | <$5M | AI Deep Dive |
| Beach Products Inc. | Manufacturing | $481,600 | $487,834 | 44 | $15.5M | AI Deep Dive |
| The Highland Consulting Group Inc. | Professional, Scientific, and Technical Services | $343,075 | $346,167 | 16 | <$5M | AI Deep Dive |
| Jjej INC | Unknown | $300,200 | $303,194 | 49 | N/A | AI Deep Dive |
| Chesland Inc. | Accommodation and Food Services | $292,671 | $295,085 | 63 | $11.2M | AI Deep Dive |
| Harbourside, Inc. | Accommodation and Food Services | $285,540 | $288,011 | 31 | $5.5M | AI Deep Dive |
| Bridges Land Management, Inc. | Administrative and Support and Waste Management | $262,900 | $265,263 | 67 | $14.5M | AI Deep Dive |
| Bud's Woodfire Oven, LLC | Unknown | $247,900 | $251,079 | 74 | N/A | AI Deep Dive |
| Environmental Concern INC | Agriculture, Forestry, Fishing and Hunting | $168,369 | $169,608 | 15 | N/A | AI Deep Dive |
| Environmental Concern INC | Agriculture, Forestry, Fishing and Hunting | $166,000 | $167,222 | 15 | N/A | AI Deep Dive |
| Shaw's Incorporated | Manufacturing | $162,700 | $164,158 | 10 | <$5M | AI Deep Dive |
| Chesland, Inc. | Accommodation and Food Services | $128,800 | $130,289 | 63 | $11.2M | AI Deep Dive |
| St. Michaels Winery, Llc. | Retail Trade | $119,861 | $120,757 | 12 | <$5M | AI Deep Dive |
| Dobson Lawn & Landscape INC | Administrative and Support and Waste Management | $119,000 | $120,021 | 19 | <$5M | AI Deep Dive |
| Higgins & Spencer, Inc. | Retail Trade | $116,900 | $118,047 | 12 | <$5M | AI Deep Dive |
| Rupert's Bar & Tea Room, LLC | Accommodation and Food Services | $114,500 | $115,952 | 11 | <$5M | AI Deep Dive |
| Hhlrllc. | Accommodation and Food Services | $112,895 | $113,695 | 10 | <$5M | AI Deep Dive |
| Carpenter Street INC | Accommodation and Food Services | $105,300 | $106,252 | 28 | <$5M | AI Deep Dive |
| Madison Enterprises LLC - DBA Foxy's Harbor Grille | Accommodation and Food Services | $94,600 | $95,694 | 15 | <$5M | AI Deep Dive |
| Guyette & Deeter INC | Retail Trade | $92,900 | $93,584 | 9 | <$5M | AI Deep Dive |
| The Lumberyard, Inc. | Retail Trade | $88,200 | $89,128 | 6 | <$5M | AI Deep Dive |
| Hhlr LLC | Accommodation and Food Services | $80,345 | $81,251 | 21 | <$5M | AI Deep Dive |
| Saint Michaels Ventures, LLC | Professional, Scientific, and Technical Services | $74,500 | $75,304 | 9 | <$5M | AI Deep Dive |
| Clark & Cummings LLC | Accommodation and Food Services | $72,700 | $73,616 | 14 | <$5M | AI Deep Dive |