| Annapolis to Olympia Heights (Florida) | 941.95 mi (1,515.93 km) |
| Annapolis to Omaha (Nebraska) | 1,042.68 mi (1,678.03 km) |
| Annapolis to On Top of the World Designated Place (Florida) | 757.29 mi (1,218.74 km) |
| Annapolis to Onalaska (Wisconsin) | 832.47 mi (1,339.72 km) |
| Annapolis to Oneida (New York) | 287.09 mi (462.03 km) |
| Annapolis to Oneonta (New York) | 252.25 mi (405.96 km) |
| Annapolis to Ontario (California) | 2,288.44 mi (3,682.89 km) |
| Annapolis to Ontario (Oregon) | 2,101.68 mi (3,382.33 km) |
| Annapolis to Opa-locka (Florida) | 928.97 mi (1,495.03 km) |
| Annapolis to Opelika (Alabama) | 660.55 mi (1,063.06 km) |
| Annapolis to Opelousas (Louisiana) | 1,057.12 mi (1,701.26 km) |
| Annapolis to Orange (California) | 2,305.78 mi (3,710.79 km) |
| Annapolis to Orange (Texas) | 1,153.74 mi (1,856.77 km) |
| Annapolis to Orange City (Florida) | 745.32 mi (1,199.48 km) |
| Annapolis to Orangeburg (South Carolina) | 449.70 mi (723.72 km) |
