| Sleepy Hollow to Oskaloosa (Iowa) | 974.00 mi (1,567.50 km) |
| Sleepy Hollow to Oswego (Illinois) | 750.04 mi (1,207.08 km) |
| Sleepy Hollow to Oswego (New York) | 211.16 mi (339.83 km) |
| Sleepy Hollow to Otsego (Minnesota) | 1,032.89 mi (1,662.28 km) |
| Sleepy Hollow to Ottawa (Illinois) | 776.36 mi (1,249.43 km) |
| Sleepy Hollow to Ottawa (Kansas) | 1,144.79 mi (1,842.37 km) |
| Sleepy Hollow to Ottumwa (Iowa) | 964.46 mi (1,552.15 km) |
| Sleepy Hollow to Overland (Missouri) | 888.61 mi (1,430.08 km) |
| Sleepy Hollow to Overland Park (Kansas) | 1,109.64 mi (1,785.80 km) |
| Sleepy Hollow to Overlea (Maryland) | 183.69 mi (295.63 km) |
| Sleepy Hollow to Oviedo (Florida) | 953.12 mi (1,533.90 km) |
| Sleepy Hollow to Owasso (Oklahoma) | 1,226.17 mi (1,973.34 km) |
| Sleepy Hollow to Owatonna (Minnesota) | 1,003.75 mi (1,615.38 km) |
| Sleepy Hollow to Owensboro (Kentucky) | 742.64 mi (1,195.16 km) |
| Sleepy Hollow to Owings Mills (Maryland) | 192.86 mi (310.38 km) |
