66 official trails lie within 25 miles of Sheridan — 232 miles in total, 25 rated easy and 15 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 4,007 ft; the median trail gains 586 ft.
| Trail | Miles | Climb | Difficulty | From town |
|---|---|---|---|---|
| Wolf Creek | 9.4 | 4,007 ft | Expert | 22 mi |
| Story Penrose | 12.0 | 2,780 ft | Expert | 18 mi |
| Solitude Loop | 27.2 | 2,185 ft | Expert | 24 mi |
| Roosevelt | 4.8 | 2,947 ft | Expert | 15 mi |
| Walker Prairie | 11.1 | 1,016 ft | Expert | 17 mi |
| Bear Gulch Trail | 4.5 | 2,397 ft | Hard | 14 mi |
| Penrose Park | 8.7 | 1,040 ft | Expert | 19 mi |
| Stockwell | 6.3 | 1,663 ft | Hard | 19 mi |
| Kenny Wood | 5.5 | 1,369 ft | Hard | 16 mi |
| Freeze Out | 3.7 | 2,082 ft | Hard | 23 mi |
| Quartz Creek | 5.4 | 1,144 ft | Hard | 17 mi |
| Spear Lake | 4.7 | 884 ft | Hard | 24 mi |
| Rock Chuck Pass | 4.4 | 1,372 ft | Hard | 23 mi |
| Little Goose | 3.2 | 1,517 ft | Moderate | 21 mi |
| Sawmill | 4.4 | 1,158 ft | Hard | 23 mi |
| Alden Creek | 2.4 | 1,705 ft | Moderate | 15 mi |
| Hendrick Ridge | 3.7 | 857 ft | Hard | 17 mi |
| Bishop Mine | 3.2 | 1,133 ft | Moderate | 19 mi |
| North Piney | 3.6 | 1,089 ft | Moderate | 16 mi |
| Smith Creek | 2.0 | 1,473 ft | Moderate | 23 mi |
| Antler Creek | 3.2 | 992 ft | Moderate | 20 mi |
| Taylor Graves | 3.5 | 890 ft | Moderate | 24 mi |
| Spear Lake Trail | 3.9 | 615 ft | Moderate | 24 mi |
| Loch Creek | 2.3 | 955 ft | Moderate | 18 mi |
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