| Sleepy Hollow to Winder (Georgia) | 728.46 mi (1,172.34 km) |
| Sleepy Hollow to Windsor (California) | 2,568.75 mi (4,134.01 km) |
| Sleepy Hollow to Windsor (Colorado) | 1,616.29 mi (2,601.17 km) |
| Sleepy Hollow to Winfield (Kansas) | 1,259.85 mi (2,027.53 km) |
| Sleepy Hollow to Winnetka (Illinois) | 719.24 mi (1,157.50 km) |
| Sleepy Hollow to Winona (Minnesota) | 926.29 mi (1,490.72 km) |
| Sleepy Hollow to Winston-Salem (North Carolina) | 487.50 mi (784.55 km) |
| Sleepy Hollow to Winter Garden (Florida) | 970.61 mi (1,562.04 km) |
| Sleepy Hollow to Winter Gardens (California) | 2,418.53 mi (3,892.24 km) |
| Sleepy Hollow to Winter Haven (Florida) | 1,006.61 mi (1,619.99 km) |
| Sleepy Hollow to Winter Park (Florida) | 960.71 mi (1,546.12 km) |
| Sleepy Hollow to Winter Springs (Florida) | 953.21 mi (1,534.04 km) |
| Sleepy Hollow to Winterville (North Carolina) | 429.31 mi (690.91 km) |
| Sleepy Hollow to Winton (California) | 2,484.60 mi (3,998.58 km) |
| Sleepy Hollow to Wisconsin Rapids (Wisconsin) | 839.49 mi (1,351.03 km) |
