| Sleepy Hollow to Southern Pines (North Carolina) | 506.29 mi (814.80 km) |
| Sleepy Hollow to Southfield (Michigan) | 492.75 mi (793.01 km) |
| Sleepy Hollow to Southgate (Michigan) | 487.69 mi (784.87 km) |
| Sleepy Hollow to Southlake (Texas) | 1,396.18 mi (2,246.93 km) |
| Sleepy Hollow to Spanaway (Washington) | 2,404.91 mi (3,870.32 km) |
| Sleepy Hollow to Spanish Fork (Utah) | 1,966.84 mi (3,165.33 km) |
| Sleepy Hollow to Spanish Lake (Missouri) | 878.52 mi (1,413.85 km) |
| Sleepy Hollow to Spanish Springs (Nevada) | 2,384.62 mi (3,837.67 km) |
| Sleepy Hollow to Sparks (Nevada) | 2,388.72 mi (3,844.28 km) |
| Sleepy Hollow to Spartanburg (South Carolina) | 609.94 mi (981.60 km) |
| Sleepy Hollow to Spearfish (South Dakota) | 1,527.46 mi (2,458.20 km) |
| Sleepy Hollow to Speedway (Indiana) | 656.36 mi (1,056.31 km) |
| Sleepy Hollow to Spencer (Iowa) | 1,096.82 mi (1,765.16 km) |
| Sleepy Hollow to Spokane (Washington) | 2,168.59 mi (3,490.00 km) |
| Sleepy Hollow to Spokane Valley (Washington) | 2,159.40 mi (3,475.22 km) |
