| Sleepy Hollow to Orangeburg (South Carolina) | 650.36 mi (1,046.65 km) |
| Sleepy Hollow to Orangevale (California) | 2,484.60 mi (3,998.58 km) |
| Sleepy Hollow to Orchards (Washington) | 2,425.66 mi (3,903.73 km) |
| Sleepy Hollow to Orcutt (California) | 2,540.77 mi (4,088.97 km) |
| Sleepy Hollow to Oregon (Ohio) | 496.92 mi (799.71 km) |
| Sleepy Hollow to Oregon (Wisconsin) | 805.42 mi (1,296.19 km) |
| Sleepy Hollow to Oregon City (Oregon) | 2,433.01 mi (3,915.55 km) |
| Sleepy Hollow to Orem (Utah) | 1,966.65 mi (3,165.02 km) |
| Sleepy Hollow to Orinda (California) | 2,552.46 mi (4,107.79 km) |
| Sleepy Hollow to Orland Park (Illinois) | 725.68 mi (1,167.86 km) |
| Sleepy Hollow to Orlando (Florida) | 968.21 mi (1,558.19 km) |
| Sleepy Hollow to Ormond Beach (Florida) | 910.62 mi (1,465.50 km) |
| Sleepy Hollow to Oro Valley (Arizona) | 2,121.85 mi (3,414.78 km) |
| Sleepy Hollow to Oroville (California) | 2,483.92 mi (3,997.48 km) |
| Sleepy Hollow to Oshkosh (Wisconsin) | 773.33 mi (1,244.56 km) |
