| Sleepy Hollow to Storm Lake (Iowa) | 1,099.43 mi (1,769.36 km) |
| Sleepy Hollow to Storrs (Connecticut) | 97.38 mi (156.72 km) |
| Sleepy Hollow to Stoughton (Wisconsin) | 796.99 mi (1,282.64 km) |
| Sleepy Hollow to Stow (Ohio) | 393.44 mi (633.18 km) |
| Sleepy Hollow to Streamwood (Illinois) | 741.53 mi (1,193.38 km) |
| Sleepy Hollow to Streator (Illinois) | 777.72 mi (1,251.61 km) |
| Sleepy Hollow to Streetsboro (Ohio) | 388.73 mi (625.60 km) |
| Sleepy Hollow to Strongsville (Ohio) | 413.88 mi (666.08 km) |
| Sleepy Hollow to Stuart (Florida) | 1,026.27 mi (1,651.62 km) |
| Sleepy Hollow to Stuarts Draft (Virginia) | 347.43 mi (559.14 km) |
| Sleepy Hollow to Sturgis (Michigan) | 599.51 mi (964.82 km) |
| Sleepy Hollow to Suamico (Wisconsin) | 758.24 mi (1,220.27 km) |
| Sleepy Hollow to Sudley (Virginia) | 249.43 mi (401.42 km) |
| Sleepy Hollow to Suffern (New York) | 14.13 mi (22.73 km) |
| Sleepy Hollow to Suffolk (Virginia) | 338.33 mi (544.49 km) |
