| Sleepy Hollow to Yonkers (New York) | 10.16 mi (16.35 km) |
| Sleepy Hollow to Yorba Linda (California) | 2,431.12 mi (3,912.51 km) |
| Sleepy Hollow to York (Pennsylvania) | 169.18 mi (272.27 km) |
| Sleepy Hollow to Yorktown (Indiana) | 613.07 mi (986.64 km) |
| Sleepy Hollow to Yorkville (Illinois) | 755.96 mi (1,216.60 km) |
| Sleepy Hollow to Youngstown (Ohio) | 352.63 mi (567.51 km) |
| Sleepy Hollow to Youngsville (Louisiana) | 1,266.19 mi (2,037.74 km) |
| Sleepy Hollow to Ypsilanti (Michigan) | 509.10 mi (819.31 km) |
| Sleepy Hollow to Yuba City (California) | 2,495.72 mi (4,016.48 km) |
| Sleepy Hollow to Yucaipa (California) | 2,389.03 mi (3,844.78 km) |
| Sleepy Hollow to Yucca Valley (California) | 2,354.13 mi (3,788.60 km) |
| Sleepy Hollow to Yukon (Oklahoma) | 1,346.48 mi (2,166.95 km) |
| Sleepy Hollow to Yulee (Florida) | 840.50 mi (1,352.65 km) |
| Sleepy Hollow to Yuma (Arizona) | 2,302.04 mi (3,704.78 km) |
| Sleepy Hollow to Zachary (Louisiana) | 1,202.99 mi (1,936.03 km) |
