| Winston-Salem to Orangeburg (South Carolina) | 183.59 mi (295.46 km) |
| Winston-Salem to Orangevale (California) | 2,236.79 mi (3,599.76 km) |
| Winston-Salem to Orchards (Washington) | 2,275.61 mi (3,662.24 km) |
| Winston-Salem to Orcutt (California) | 2,244.89 mi (3,612.80 km) |
| Winston-Salem to Oregon (Ohio) | 419.58 mi (675.24 km) |
| Winston-Salem to Oregon (Wisconsin) | 676.68 mi (1,089.00 km) |
| Winston-Salem to Oregon City (Oregon) | 2,278.01 mi (3,666.10 km) |
| Winston-Salem to Orem (Utah) | 1,722.15 mi (2,771.54 km) |
| Winston-Salem to Orinda (California) | 2,297.05 mi (3,696.74 km) |
| Winston-Salem to Orland Park (Illinois) | 558.06 mi (898.11 km) |
| Winston-Salem to Orlando (Florida) | 530.60 mi (853.92 km) |
| Winston-Salem to Ormond Beach (Florida) | 472.66 mi (760.68 km) |
| Winston-Salem to Oro Valley (Arizona) | 1,764.91 mi (2,840.34 km) |
| Winston-Salem to Oroville (California) | 2,247.29 mi (3,616.66 km) |
| Winston-Salem to Oshkosh (Wisconsin) | 700.72 mi (1,127.70 km) |
