| Winona to Shelbyville (Tennessee) | 652.23 mi (1,049.67 km) |
| Winona to Shelton (Connecticut) | 957.99 mi (1,541.73 km) |
| Winona to Shelton (Washington) | 1,524.24 mi (2,453.03 km) |
| Winona to Shenandoah (Louisiana) | 943.73 mi (1,518.79 km) |
| Winona to Shepherdsville (Kentucky) | 521.83 mi (839.80 km) |
| Winona to Sheridan (Wyoming) | 755.42 mi (1,215.73 km) |
| Winona to Sherman (Texas) | 767.55 mi (1,235.25 km) |
| Winona to Sherrelwood (Colorado) | 743.30 mi (1,196.22 km) |
| Winona to Sherwood (Arkansas) | 636.28 mi (1,023.99 km) |
| Winona to Sherwood (Oregon) | 1,523.97 mi (2,452.60 km) |
| Winona to Shiloh (Illinois) | 390.52 mi (628.49 km) |
| Winona to Shiloh (Ohio) | 481.04 mi (774.16 km) |
| Winona to Shiloh (Pennsylvania) | 812.58 mi (1,307.73 km) |
| Winona to Shirley (New York) | 982.26 mi (1,580.80 km) |
| Winona to Shively (Kentucky) | 506.09 mi (814.47 km) |
