| Belle Meade Educational Resources Center | Educational Services | $200,000 | $26,373 | 5 | N/A |  Research |
| Copper Fox Distillery Enterprises, LLC | Manufacturing | $112,900 | $113,960 | 21 | $7.4M | Research |
| The Thornton River Group, LLC | Accommodation and Food Services | $102,343 | $103,107 | 10 | <$5M | Research |
| Piedmont Inn LLC | Accommodation and Food Services | $70,742 | $71,257 | 8 | <$5M | Research |
| B&b Service Center LLC | Other Services (except Public Administration) | $61,600 | $62,315 | 6 | <$5M | Research |
| Main Street Galleries, LLC | Retail Trade | $47,330 | $47,920 | 2 | <$5M | Research |
| Haley Fine Art (rappahannock Co) | Retail Trade | $47,330 | $47,568 | 2 | <$5M | Research |
| Piedmont Inn, LLC | Accommodation and Food Services | $45,838 | $46,198 | 3 | <$5M | Research |
| Shaws Services Inc. | Other Services (except Public Administration) | $43,749 | $44,019 | 5 | <$5M | Research |
| Sperryville Trading Inc. | Accommodation and Food Services | $41,790 | $42,070 | 6 | <$5M | Research |
| Before & After - Operating LLC | Accommodation and Food Services | $37,628 | $37,876 | 10 | <$5M | Research |
| Gourmet Express, Llc, the | Accommodation and Food Services | $36,970 | $39,976 | 6 | <$5M | Research |
| The Gourmet Express LLC | Accommodation and Food Services | $36,750 | $37,100 | 8 | <$5M | Research |
| Mw/a LLC | Real Estate and Rental and Leasing | $33,520 | $33,739 | 4 | <$5M | Research |
| Pen Druid Brewery Company LLC | Accommodation and Food Services | $33,121 | $33,391 | 4 | <$5M | Research |
| One Tree Island, LLC | Accommodation and Food Services | $31,910 | $32,195 | 6 | <$5M | Research |
| Sperryville Trading Inc. | Accommodation and Food Services | $31,200 | $31,395 | 8 | <$5M | Research |
| Riverside Auto Service LLC | Other Services (except Public Administration) | $25,500 | $18,664 | 2 | <$5M | Research |
| Woods Gymnastics, LLC | Educational Services | $25,100 | $25,253 | 4 | <$5M | Research |
| Pen Druid Brewery Company LLC | Manufacturing | $23,658 | $23,875 | 5 | <$5M | Research |
| Before & Aftert - Operating LLC | Accommodation and Food Services | $20,863 | $20,979 | 5 | <$5M | Research |
| River Bend Strategies Inc. | Professional, Scientific, and Technical Services | $20,835 | $21,012 | 1 | <$5M | Research |
| River Bend Strategies, Inc. | Professional, Scientific, and Technical Services | $20,833 | $21,023 | 1 | <$5M | Research |
| Home Tech Construction Services, Llc. | Construction | $20,833 | $21,025 | 6 | <$5M | Research |
| Paul Larner | Real Estate and Rental and Leasing | $20,832 | $20,994 | 1 | <$5M | Research |