| Sleepy Hollow to Odenton (Maryland) | 204.61 mi (329.29 km) |
| Sleepy Hollow to Odessa (Texas) | 1,695.35 mi (2,728.39 km) |
| Sleepy Hollow to Ogden (Utah) | 1,965.52 mi (3,163.20 km) |
| Sleepy Hollow to Oildale (California) | 2,453.24 mi (3,948.10 km) |
| Sleepy Hollow to Ojus (Florida) | 1,106.01 mi (1,779.95 km) |
| Sleepy Hollow to Okemos (Michigan) | 553.04 mi (890.03 km) |
| Sleepy Hollow to Oklahoma City (Oklahoma) | 1,335.08 mi (2,148.60 km) |
| Sleepy Hollow to Okmulgee (Oklahoma) | 1,253.65 mi (2,017.55 km) |
| Sleepy Hollow to Olathe (Kansas) | 1,116.63 mi (1,797.05 km) |
| Sleepy Hollow to Old Jamestown (Missouri) | 881.58 mi (1,418.76 km) |
| Sleepy Hollow to Oldsmar (Florida) | 1,029.49 mi (1,656.81 km) |
| Sleepy Hollow to Olean (New York) | 245.30 mi (394.78 km) |
| Sleepy Hollow to Olive Branch (Mississippi) | 965.17 mi (1,553.29 km) |
| Sleepy Hollow to Olivehurst (California) | 2,492.83 mi (4,011.83 km) |
| Sleepy Hollow to Olney (Maryland) | 216.01 mi (347.63 km) |
