| Difficult Run to Olympia Heights (Florida) | 926.93 mi (1,491.75 km) |
| Difficult Run to Omaha (Nebraska) | 1,000.22 mi (1,609.70 km) |
| Difficult Run to On Top of the World Designated Place (Florida) | 733.25 mi (1,180.06 km) |
| Difficult Run to Onalaska (Wisconsin) | 795.38 mi (1,280.05 km) |
| Difficult Run to Oneida (New York) | 301.55 mi (485.30 km) |
| Difficult Run to Oneonta (New York) | 273.03 mi (439.40 km) |
| Difficult Run to Ontario (California) | 2,243.65 mi (3,610.80 km) |
| Difficult Run to Ontario (Oregon) | 2,061.80 mi (3,318.15 km) |
| Difficult Run to Opa-locka (Florida) | 914.07 mi (1,471.06 km) |
| Difficult Run to Opelika (Alabama) | 622.78 mi (1,002.27 km) |
| Difficult Run to Opelousas (Louisiana) | 1,015.37 mi (1,634.08 km) |
| Difficult Run to Orange (California) | 2,260.95 mi (3,638.64 km) |
| Difficult Run to Orange (Texas) | 1,111.36 mi (1,788.56 km) |
| Difficult Run to Orange City (Florida) | 724.55 mi (1,166.05 km) |
| Difficult Run to Orangeburg (South Carolina) | 422.02 mi (679.18 km) |
