33 official trails lie within 25 miles of Winona — 256 miles in total, 29 rated easy and 1 hard or expert. Every distance and elevation figure below is computed from the agency centerline and a 10 m elevation model, not crowd-sourced.
The biggest climb nearby gains 466 ft; the median trail gains 77 ft.
| Trail | Miles | Climb | Difficulty | From town |
|---|---|---|---|---|
| Trout Valley Trail | 7.7 | 466 ft | Hard | 15 mi |
| Dakota Trail | 3.2 | 274 ft | Moderate | 19 mi |
| Park Trail | 5.0 | 125 ft | Moderate | 16 mi |
| Snake Creek Management Unit Trails | 4.3 | 199 ft | Moderate | 22 mi |
| Zumbro River | 164.7 | 456 ft | Easy | 21 mi |
| Ope! | 1.5 | 453 ft | Easy | 1 mi |
| Snake Creek Trail | 2.4 | 317 ft | Easy | 21 mi |
| Whitewater River | 17.5 | 77 ft | Easy | 18 mi |
| Quarry | 1.2 | 288 ft | Easy | 1 mi |
| Coyote Point Trail | 1.1 | 321 ft | Easy | 19 mi |
| Low Rollers | 1.7 | 187 ft | Easy | 1 mi |
| Cistern | 1.0 | 313 ft | Easy | 1 mi |
| High Rollers | 1.2 | 189 ft | Easy | 1 mi |
| Kings Bluff | 1.3 | 85 ft | Easy | 15 mi |
| Wildwood | 1.6 | 45 ft | Easy | 1 mi |
| Meadow Trail | 1.3 | 40 ft | Easy | 19 mi |
| Mississippi River | 2.0 | 6 ft | Easy | 9 mi |
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