| Sleepy Hollow to Olympia (Washington) | 2,427.48 mi (3,906.64 km) |
| Sleepy Hollow to Olympia Heights (Florida) | 1,124.65 mi (1,809.95 km) |
| Sleepy Hollow to Omaha (Nebraska) | 1,150.40 mi (1,851.39 km) |
| Sleepy Hollow to On Top of the World Designated Place (Florida) | 953.99 mi (1,535.30 km) |
| Sleepy Hollow to Onalaska (Wisconsin) | 902.26 mi (1,452.04 km) |
| Sleepy Hollow to Oneida (New York) | 164.92 mi (265.42 km) |
| Sleepy Hollow to Oneonta (New York) | 112.41 mi (180.91 km) |
| Sleepy Hollow to Ontario (California) | 2,418.18 mi (3,891.68 km) |
| Sleepy Hollow to Ontario (Oregon) | 2,177.91 mi (3,505.02 km) |
| Sleepy Hollow to Opa-locka (Florida) | 1,111.51 mi (1,788.80 km) |
| Sleepy Hollow to Opelika (Alabama) | 860.99 mi (1,385.63 km) |
| Sleepy Hollow to Opelousas (Louisiana) | 1,250.46 mi (2,012.42 km) |
| Sleepy Hollow to Orange (California) | 2,436.23 mi (3,920.73 km) |
| Sleepy Hollow to Orange (Texas) | 1,344.91 mi (2,164.43 km) |
| Sleepy Hollow to Orange City (Florida) | 938.16 mi (1,509.82 km) |
