| Difficult Run to Yonkers (New York) | 232.26 mi (373.79 km) |
| Difficult Run to Yorba Linda (California) | 2,256.15 mi (3,630.93 km) |
| Difficult Run to York (Pennsylvania) | 80.49 mi (129.54 km) |
| Difficult Run to Yorktown (Indiana) | 443.80 mi (714.23 km) |
| Difficult Run to Yorkville (Illinois) | 614.93 mi (989.63 km) |
| Difficult Run to Youngstown (Ohio) | 231.38 mi (372.36 km) |
| Difficult Run to Youngsville (Louisiana) | 1,030.28 mi (1,658.07 km) |
| Difficult Run to Ypsilanti (Michigan) | 401.99 mi (646.94 km) |
| Difficult Run to Yuba City (California) | 2,353.41 mi (3,787.44 km) |
| Difficult Run to Yucaipa (California) | 2,213.56 mi (3,562.38 km) |
| Difficult Run to Yucca Valley (California) | 2,178.06 mi (3,505.25 km) |
| Difficult Run to Yukon (Oklahoma) | 1,144.93 mi (1,842.59 km) |
| Difficult Run to Yulee (Florida) | 619.17 mi (996.45 km) |
| Difficult Run to Yuma (Arizona) | 2,115.80 mi (3,405.05 km) |
| Difficult Run to Zachary (Louisiana) | 966.99 mi (1,556.23 km) |
