| Sleepy Hollow to Seymour (Indiana) | 652.42 mi (1,049.97 km) |
| Sleepy Hollow to Seymour (Tennessee) | 644.49 mi (1,037.21 km) |
| Sleepy Hollow to Shady Hills (Florida) | 1,004.31 mi (1,616.28 km) |
| Sleepy Hollow to Shafter (California) | 2,460.72 mi (3,960.15 km) |
| Sleepy Hollow to Shaker Heights (Ohio) | 399.35 mi (642.69 km) |
| Sleepy Hollow to Shakopee (Minnesota) | 1,021.04 mi (1,643.21 km) |
| Sleepy Hollow to Sharon (Pennsylvania) | 344.79 mi (554.89 km) |
| Sleepy Hollow to Sharonville (Ohio) | 569.57 mi (916.64 km) |
| Sleepy Hollow to Shasta Lake (California) | 2,500.18 mi (4,023.65 km) |
| Sleepy Hollow to Shawnee (Kansas) | 1,113.72 mi (1,792.37 km) |
| Sleepy Hollow to Shawnee (Oklahoma) | 1,310.16 mi (2,108.49 km) |
| Sleepy Hollow to Sheboygan (Wisconsin) | 729.24 mi (1,173.60 km) |
| Sleepy Hollow to Shelby (North Carolina) | 577.80 mi (929.88 km) |
| Sleepy Hollow to Shelbyville (Indiana) | 635.96 mi (1,023.48 km) |
| Sleepy Hollow to Shelbyville (Kentucky) | 635.68 mi (1,023.03 km) |
