| Winston-Salem to Olympia (Washington) | 2,297.26 mi (3,697.08 km) |
| Winston-Salem to Olympia Heights (Florida) | 717.13 mi (1,154.10 km) |
| Winston-Salem to Omaha (Nebraska) | 921.59 mi (1,483.16 km) |
| Winston-Salem to On Top of the World Designated Place (Florida) | 497.58 mi (800.78 km) |
| Winston-Salem to Onalaska (Wisconsin) | 789.34 mi (1,270.31 km) |
| Winston-Salem to Oneida (New York) | 540.28 mi (869.50 km) |
| Winston-Salem to Oneonta (New York) | 519.18 mi (835.54 km) |
| Winston-Salem to Ontario (California) | 2,103.71 mi (3,385.59 km) |
| Winston-Salem to Ontario (Oregon) | 1,998.91 mi (3,216.94 km) |
| Winston-Salem to Opa-locka (Florida) | 704.97 mi (1,134.54 km) |
| Winston-Salem to Opelika (Alabama) | 376.26 mi (605.53 km) |
| Winston-Salem to Opelousas (Louisiana) | 782.94 mi (1,260.02 km) |
| Winston-Salem to Orange (California) | 2,119.83 mi (3,411.54 km) |
| Winston-Salem to Orange (Texas) | 882.60 mi (1,420.42 km) |
| Winston-Salem to Orange City (Florida) | 498.86 mi (802.84 km) |
