| Ski to Olympia Heights (Florida) | 4,738.68 mi (7,626.18 km) |
| Ski to Omaha (Nebraska) | 4,329.45 mi (6,967.57 km) |
| Ski to On Top of the World Designated Place (Florida) | 4,607.73 mi (7,415.43 km) |
| Ski to Onalaska (Wisconsin) | 4,041.13 mi (6,503.58 km) |
| Ski to Oneida (New York) | 3,611.00 mi (5,811.34 km) |
| Ski to Oneonta (New York) | 3,625.00 mi (5,833.88 km) |
| Ski to Ontario (California) | 5,325.81 mi (8,571.07 km) |
| Ski to Ontario (Oregon) | 4,684.32 mi (7,538.69 km) |
| Ski to Opa-locka (Florida) | 4,725.66 mi (7,605.21 km) |
| Ski to Opelika (Alabama) | 4,503.32 mi (7,247.39 km) |
| Ski to Opelousas (Louisiana) | 4,839.73 mi (7,788.80 km) |
| Ski to Orange (California) | 5,345.68 mi (8,603.05 km) |
| Ski to Orange (Texas) | 4,915.47 mi (7,910.68 km) |
| Ski to Orange City (Florida) | 4,584.50 mi (7,378.05 km) |
| Ski to Orangeburg (South Carolina) | 4,309.44 mi (6,935.38 km) |
