| Sleepy Hollow to Owosso (Michigan) | 544.39 mi (876.11 km) |
| Sleepy Hollow to Oxford (Alabama) | 836.80 mi (1,346.71 km) |
| Sleepy Hollow to Oxford (Mississippi) | 971.96 mi (1,564.21 km) |
| Sleepy Hollow to Oxford (Ohio) | 582.92 mi (938.12 km) |
| Sleepy Hollow to Oxnard (California) | 2,495.52 mi (4,016.15 km) |
| Sleepy Hollow to Oxon Hill (Maryland) | 228.76 mi (368.15 km) |
| Sleepy Hollow to Ozark (Alabama) | 933.24 mi (1,501.90 km) |
| Sleepy Hollow to Ozark (Missouri) | 1,072.38 mi (1,725.83 km) |
| Sleepy Hollow to Pace (Florida) | 1,035.97 mi (1,667.23 km) |
| Sleepy Hollow to Pacific Grove (California) | 2,571.17 mi (4,137.90 km) |
| Sleepy Hollow to Pacifica (California) | 2,574.35 mi (4,143.01 km) |
| Sleepy Hollow to Paducah (Kentucky) | 838.31 mi (1,349.13 km) |
| Sleepy Hollow to Pahrump (Nevada) | 2,275.22 mi (3,661.61 km) |
| Sleepy Hollow to Painesville (Ohio) | 384.86 mi (619.37 km) |
| Sleepy Hollow to Palatine (Illinois) | 734.67 mi (1,182.33 km) |
