| Difficult Run to Winder (Georgia) | 490.27 mi (789.02 km) |
| Difficult Run to Windsor (California) | 2,424.71 mi (3,902.20 km) |
| Difficult Run to Windsor (Colorado) | 1,464.12 mi (2,356.27 km) |
| Difficult Run to Winfield (Kansas) | 1,069.86 mi (1,721.77 km) |
| Difficult Run to Winnetka (Illinois) | 588.79 mi (947.57 km) |
| Difficult Run to Winona (Minnesota) | 820.79 mi (1,320.93 km) |
| Difficult Run to Winston-Salem (North Carolina) | 250.77 mi (403.58 km) |
| Difficult Run to Winter Garden (Florida) | 756.03 mi (1,216.71 km) |
| Difficult Run to Winter Gardens (California) | 2,237.37 mi (3,600.71 km) |
| Difficult Run to Winter Haven (Florida) | 792.89 mi (1,276.04 km) |
| Difficult Run to Winter Park (Florida) | 747.74 mi (1,203.37 km) |
| Difficult Run to Winter Springs (Florida) | 740.50 mi (1,191.71 km) |
| Difficult Run to Winterville (North Carolina) | 233.04 mi (375.03 km) |
| Difficult Run to Winton (California) | 2,331.42 mi (3,752.05 km) |
| Difficult Run to Wisconsin Rapids (Wisconsin) | 746.51 mi (1,201.40 km) |
