About hiking in Winona County

Winona County, Minnesota has 43 named trails tagged for hiking, covering 42.3 miles, an average of 1.0 mile each. The longest is Lake Park Path, at 5.1 miles. 1 runs 5 miles or longer.

What the hiking trails in Winona County are like

By length, 26 are under a mile, 16 run 1 to 5 miles, and 1 is 5 miles or longer. 1 is a loop, ending where it starts; the longest is Sugar Loaf Trail, at 1.3 miles.

Of the 22 with a difficulty rating, 13 easy, 8 moderate, and 1 hard. Of the 43 with measured elevation, Dakota climbs the most, about 1,670 ft.

All 43 hiking trails, longest first

Lake Park PathHikeMTB5.1 mi DakotaHike3.2 mi WildwoodHike2.5 mi Secluded RoadHikeMTB2.4 mi RattlesnakeHike2.2 mi Low RollersHikeMTB1.8 mi Chickadee CircuitHikeMTB1.7 mi Upper TrailHike1.7 mi ChimneyRockHike1.7 mi Ope!Hike1.5 mi Sugar Loaf TrailHike1.3 mi QuarryHike1.2 mi High RollersHikeMTB1.2 mi DikeHike1.1 mi Coyote PointHike1.1 mi CisternHike1.0 mi State forest accessHikeMTB1.0 mi OrchardHike0.9 mi Trout Run Creek Self-Guided TrailHike0.9 mi MeadowHike0.9 mi River TrailHike0.8 mi Powerline TrailHike0.6 mi Old quarry roadHike0.6 mi Lake Winona Bike PathHikeMTB0.5 mi Troll StrollHikeMTB0.4 mi Lower quarry LoopHike0.4 mi Valley TrailHike0.4 mi Eagle Watchers trailHike0.4 mi Meadow TrailHike0.4 mi loging trackHikeMTB0.4 mi King's Bluff TrailHike0.3 mi Lower ConnectorHike0.3 mi Salad Bar TrailHike0.3 mi ValleyHike0.2 mi MinneiskaHike0.2 mi Dahl ConnectorHike0.2 mi Horse TrailHike0.2 mi Upper ConnectorHike0.2 mi Buelow DriveHikeMTB0.2 mi ICE WALLHike0.2 mi Apple Blossom Overlook TrailHike0.2 mi ConectorHike0.2 mi Group Camp 3 Access OnlyHike0.1 mi

← All Winona County trails

Trail geometry from OpenStreetMap contributors, licensed ODbL. Elevation from the USGS 3D Elevation Program. Compiled and published by Trailmonger · trail data last rebuilt October 4, 2026.