| Difficult Run to Orangevale (California) | 2,339.27 mi (3,764.69 km) |
| Difficult Run to Orchards (Washington) | 2,324.31 mi (3,740.62 km) |
| Difficult Run to Orcutt (California) | 2,374.65 mi (3,821.63 km) |
| Difficult Run to Oregon (Ohio) | 372.70 mi (599.81 km) |
| Difficult Run to Oregon (Wisconsin) | 686.64 mi (1,105.05 km) |
| Difficult Run to Oregon City (Oregon) | 2,329.41 mi (3,748.83 km) |
| Difficult Run to Orem (Utah) | 1,819.90 mi (2,928.84 km) |
| Difficult Run to Orinda (California) | 2,404.06 mi (3,868.96 km) |
| Difficult Run to Orland Park (Illinois) | 584.66 mi (940.92 km) |
| Difficult Run to Orlando (Florida) | 755.66 mi (1,216.12 km) |
| Difficult Run to Ormond Beach (Florida) | 697.22 mi (1,122.07 km) |
| Difficult Run to Oro Valley (Arizona) | 1,928.57 mi (3,103.73 km) |
| Difficult Run to Oroville (California) | 2,343.55 mi (3,771.57 km) |
| Difficult Run to Oshkosh (Wisconsin) | 679.09 mi (1,092.89 km) |
| Difficult Run to Oskaloosa (Iowa) | 823.85 mi (1,325.85 km) |
