| Winston-Salem to Oskaloosa (Iowa) | 756.71 mi (1,217.81 km) |
| Winston-Salem to Oswego (Illinois) | 580.28 mi (933.88 km) |
| Winston-Salem to Oswego (New York) | 545.44 mi (877.80 km) |
| Winston-Salem to Otsego (Minnesota) | 941.51 mi (1,515.21 km) |
| Winston-Salem to Ottawa (Illinois) | 586.73 mi (944.25 km) |
| Winston-Salem to Ottawa (Kansas) | 840.85 mi (1,353.21 km) |
| Winston-Salem to Ottumwa (Iowa) | 738.54 mi (1,188.56 km) |
| Winston-Salem to Overland (Missouri) | 582.66 mi (937.70 km) |
| Winston-Salem to Overland Park (Kansas) | 812.92 mi (1,308.26 km) |
| Winston-Salem to Overlea (Maryland) | 304.27 mi (489.68 km) |
| Winston-Salem to Oviedo (Florida) | 517.22 mi (832.38 km) |
| Winston-Salem to Owasso (Oklahoma) | 867.33 mi (1,395.83 km) |
| Winston-Salem to Owatonna (Minnesota) | 878.27 mi (1,413.43 km) |
| Winston-Salem to Owensboro (Kentucky) | 395.44 mi (636.40 km) |
| Winston-Salem to Owings Mills (Maryland) | 296.90 mi (477.82 km) |
