| Cumberland to Winder (Georgia) | 477.60 mi (768.63 km) |
| Cumberland to Windsor (California) | 2,339.31 mi (3,764.76 km) |
| Cumberland to Windsor (Colorado) | 1,379.55 mi (2,220.17 km) |
| Cumberland to Winfield (Kansas) | 996.01 mi (1,602.92 km) |
| Cumberland to Winnetka (Illinois) | 498.72 mi (802.62 km) |
| Cumberland to Winona (Minnesota) | 729.57 mi (1,174.13 km) |
| Cumberland to Winston-Salem (North Carolina) | 258.50 mi (416.02 km) |
| Cumberland to Winter Garden (Florida) | 784.45 mi (1,262.45 km) |
| Cumberland to Winter Gardens (California) | 2,161.35 mi (3,478.36 km) |
| Cumberland to Winter Haven (Florida) | 821.63 mi (1,322.29 km) |
| Cumberland to Winter Park (Florida) | 777.75 mi (1,251.66 km) |
| Cumberland to Winter Springs (Florida) | 770.84 mi (1,240.54 km) |
| Cumberland to Winterville (North Carolina) | 294.37 mi (473.74 km) |
| Cumberland to Winton (California) | 2,247.77 mi (3,617.43 km) |
| Cumberland to Wisconsin Rapids (Wisconsin) | 654.96 mi (1,054.06 km) |
