| Sleepy Hollow to Oakleaf Plantation (Florida) | 876.36 mi (1,410.36 km) |
| Sleepy Hollow to Oakley (California) | 2,525.05 mi (4,063.68 km) |
| Sleepy Hollow to Oakton (Virginia) | 236.95 mi (381.34 km) |
| Sleepy Hollow to Oakville (Missouri) | 890.95 mi (1,433.85 km) |
| Sleepy Hollow to Oatfield (Oregon) | 2,432.17 mi (3,914.20 km) |
| Sleepy Hollow to Ocala (Florida) | 945.80 mi (1,522.12 km) |
| Sleepy Hollow to Ocean Acres (New Jersey) | 95.76 mi (154.11 km) |
| Sleepy Hollow to Ocean City (New Jersey) | 131.88 mi (212.24 km) |
| Sleepy Hollow to Ocean Pines (Maryland) | 199.04 mi (320.33 km) |
| Sleepy Hollow to Ocean Pointe (Hawaii) | 4,968.98 mi (7,996.80 km) |
| Sleepy Hollow to Ocean Springs (Mississippi) | 1,112.60 mi (1,790.56 km) |
| Sleepy Hollow to Oceanside (California) | 2,426.67 mi (3,905.34 km) |
| Sleepy Hollow to Oceanside (New York) | 34.14 mi (54.94 km) |
| Sleepy Hollow to Ocoee (Florida) | 966.65 mi (1,555.67 km) |
| Sleepy Hollow to Oconomowoc (Wisconsin) | 761.35 mi (1,225.27 km) |
