| Metompkin Bay Oyster Co. Inc. | Manufacturing | $40,025 | $40,250 | 6 | <$5M |  AI Deep Dive |
| Linton's Seafood, Inc. | Wholesale Trade | $39,723 | $40,366 | 7 | <$5M | AI Deep Dive |
| Chesapeake Boats LLC | Manufacturing | $38,600 | $38,905 | 7 | <$5M | AI Deep Dive |
| Chesapeake Custom Boats LLC | Manufacturing | $38,600 | $38,765 | 3 | <$5M | AI Deep Dive |
| Bayside Home Center, INC | Retail Trade | $38,500 | $38,929 | 8 | <$5M | AI Deep Dive |
| Eddie Heath's Crab Pots & Supply Co., INC | Agriculture, Forestry, Fishing and Hunting | $37,401 | $37,575 | 10 | <$5M | AI Deep Dive |
| Somerset Health Services LLC | Retail Trade | $32,300 | $32,754 | 5 | <$5M | AI Deep Dive |
| The Marion Pharmacy INC | Retail Trade | $32,000 | $32,292 | 12 | <$5M | AI Deep Dive |
| Marshall S Marine LLC | Manufacturing | $31,000 | $31,295 | 6 | <$5M | AI Deep Dive |
| Marshall S Marine LLC | Retail Trade | $26,000 | $22,297 | 7 | <$5M | AI Deep Dive |
| Jed's Auto Refinishing | Other Services (except Public Administration) | $24,502 | $24,762 | 3 | <$5M | AI Deep Dive |
| Living Hope Ministries of Eastern Shore INC | Other Services (except Public Administration) | $24,000 | $24,169 | 7 | N/A | AI Deep Dive |
| B W Electric INC | Construction | $23,300 | $7,013 | 3 | <$5M | AI Deep Dive |
| Cullen Farms INC | Agriculture, Forestry, Fishing and Hunting | $22,917 | $23,030 | 5 | <$5M | AI Deep Dive |
| Puffinburger Inc. | Retail Trade | $22,777 | $22,914 | 13 | <$5M | AI Deep Dive |
| Puffinburger, INC | Retail Trade | $22,700 | $22,868 | 13 | <$5M | AI Deep Dive |
| William Colona | Wholesale Trade | $22,500 | $22,781 | 3 | <$5M | AI Deep Dive |
| James Deppen | Administrative and Support and Waste Management | $20,833 | $0 | 1 | <$5M | AI Deep Dive |
| Jill Jicha | Professional, Scientific, and Technical Services | $20,833 | $20,955 | 1 | <$5M | AI Deep Dive |
| Terry Miles | Accommodation and Food Services | $20,832 | $20,927 | 1 | <$5M | AI Deep Dive |
| Jason Saurbaugh | Accommodation and Food Services | $20,208 | $20,370 | 1 | <$5M | AI Deep Dive |
| Ranchhodrai Sai Ram & Hanuman Corp | Retail Trade | $19,300 | $19,455 | 6 | <$5M | AI Deep Dive |
| Jean-Daniel Berard | Transportation and Warehousing | $19,180 | $19,354 | 1 | <$5M | AI Deep Dive |
| Jean-Daniel Berard | Transportation and Warehousing | $19,180 | $19,395 | 1 | <$5M | AI Deep Dive |
| Samuel F. Davis Enterprises, INC | Retail Trade | $18,800 | $19,038 | 7 | <$5M | AI Deep Dive |