15 trails
| Name | Distance | Ascent | Descent | OpenStreetMap Relation |
|---|---|---|---|---|
| Winona - Winona Way Trail | 5.0 mi | 323 ft | 422 ft |  19390363 |
| Winona - Bills Belly Trail | 2.1 mi | 131 ft | 114 ft | 19393630 |
| Winona - Raspberry Trail | 2.0 mi | 207 ft | 179 ft | 19393616 |
| Winona - Shady Shuttle | 1.9 mi | 203 ft | 107 ft | 19390371 |
| Winona - Backus Bend Trail | 1.8 mi | 180 ft | 76 ft | 19390372 |
| Winona - Hiscock Trail | 1.7 mi | 187 ft | 0 ft | 19393614 |
| Winona - Hawley Tucker Roads | 1.5 mi | 165 ft | 0 ft | 19393631 |
| Winona - Little Sandy Creek | 1.0 mi | 56 ft | 128 ft | 19393628 |
| Winona - Dog Leg Trail | 0.9 mi | 60 ft | 47 ft | 19390357 |
| Winona - Stinson Creek Trail | 0.8 mi | 92 ft | 0 ft | 19393627 |
| Winona - Jimmys Jaunt Trail | 0.6 mi | 83 ft | 0 ft | 19393629 |
| Winona - Teds Turn Trail | 0.6 mi | 26 ft | 63 ft | 19393615 |
| Winona - Cross Leg Trail | 0.5 mi | 40 ft | 0 ft | 19390364 |
| Winona - Winona Way Extension | 0.4 mi | 35 ft | 0 ft | 19390358 |
| Winona - Tie Trail | 0.3 mi | 0 ft | 54 ft | 19393638 |