| Pleasantville to Oskaloosa (Iowa) | 961.65 mi (1,547.63 km) |
| Pleasantville to Oswego (Illinois) | 741.93 mi (1,194.01 km) |
| Pleasantville to Oswego (New York) | 298.83 mi (480.92 km) |
| Pleasantville to Otsego (Minnesota) | 1,053.61 mi (1,695.63 km) |
| Pleasantville to Ottawa (Illinois) | 764.43 mi (1,230.24 km) |
| Pleasantville to Ottawa (Kansas) | 1,112.97 mi (1,791.16 km) |
| Pleasantville to Ottumwa (Iowa) | 949.65 mi (1,528.32 km) |
| Pleasantville to Overland (Missouri) | 850.91 mi (1,369.41 km) |
| Pleasantville to Overland Park (Kansas) | 1,079.23 mi (1,736.86 km) |
| Pleasantville to Overlea (Maryland) | 106.86 mi (171.98 km) |
| Pleasantville to Oviedo (Florida) | 833.47 mi (1,341.34 km) |
| Pleasantville to Owasso (Oklahoma) | 1,179.71 mi (1,898.57 km) |
| Pleasantville to Owatonna (Minnesota) | 1,015.35 mi (1,634.04 km) |
| Pleasantville to Owensboro (Kentucky) | 689.33 mi (1,109.36 km) |
| Pleasantville to Owings Mills (Maryland) | 121.44 mi (195.43 km) |
