| Winona to Reedley (California) | 1,542.38 mi (2,482.23 km) |
| Winona to Reidsville (North Carolina) | 826.02 mi (1,329.36 km) |
| Winona to Reisterstown (Maryland) | 827.38 mi (1,331.53 km) |
| Winona to Rendon (Texas) | 847.58 mi (1,364.05 km) |
| Winona to Reno (Nevada) | 1,476.73 mi (2,376.57 km) |
| Winona to Renton (Washington) | 1,480.35 mi (2,382.39 km) |
| Winona to Republic (Missouri) | 486.09 mi (782.29 km) |
| Winona to Reston (Virginia) | 819.17 mi (1,318.32 km) |
| Winona to Revere (Massachusetts) | 1,043.53 mi (1,679.39 km) |
| Winona to Rexburg (Idaho) | 998.87 mi (1,607.52 km) |
| Winona to Reynoldsburg (Ohio) | 535.75 mi (862.20 km) |
| Winona to Rialto (California) | 1,531.94 mi (2,465.42 km) |
| Winona to Richardson (Texas) | 812.12 mi (1,306.98 km) |
| Winona to Richfield (Minnesota) | 97.95 mi (157.63 km) |
| Winona to Richfield (Wisconsin) | 180.31 mi (290.19 km) |
