30 official trails lie within 25 miles of Leonardtown — 59 miles in total, 29 rated easy and 0 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 150 ft; the median trail gains 49 ft.
| Trail | Miles | Climb | Difficulty | Drive from town |
|---|---|---|---|---|
| St Marys Lake Trail | 7.2 | 49 ft | Moderate | 16 min · 9 mi |
| brown trail (Maxwell Hall Natural Resource Management Area) | 1.8 | 81 ft | Easy | 45 min · 25 mi |
| Salem State Forest Trails | 3.2 | 43 ft | Easy | 11 min · 6 mi |
| White Trail (Saint Mary's River State Park) | 3.3 | 40 ft | Easy | 17 min · 8 mi |
| Horse Swamp Trail | 1.2 | 135 ft | Easy | 56 min · 35 mi |
| Woodland Creek Trail | 1.6 | 77 ft | Easy | 37 min · 22 mi |
| Swamp And Plantation Trails | 2.5 | 54 ft | Easy | 1 h 07 min · 38 mi |
| Old Parkers Creek Road Trail | 1.2 | 150 ft | Easy | 56 min · 35 mi |
| Oriole Trail | 1.7 | 61 ft | Easy | 41 min · 26 mi |
| Red Trail | 1.9 | 84 ft | Easy | 28 min · 17 mi |
| Saint Mary's City Nature Trail | 3.1 | 41 ft | Easy | 30 min · 18 mi |
| Parkers Creek Trail | 1.3 | 84 ft | Easy | 50 min · 29 mi |
| Orange Trail | 1.2 | 120 ft | Easy | 38 min · 19 mi |
| Red | 1.5 | 55 ft | Easy | 19 min · 9 mi |
| Bell Lap Trail | 1.5 | 41 ft | Easy | 11 min · 6 mi |
| Green Trail (Maxwell Hall Natural Resource Management Area) | 1.1 | 75 ft | Easy | 55 min · 29 mi |
| White | 1.1 | 66 ft | Easy | 19 min · 9 mi |
| Green - Swamp Trail | 1.1 | 54 ft | Easy | 1 h 07 min · 38 mi |
| Green Trail (Cedarville State Forest) | 1.0 | 49 ft | Easy | 1 h 07 min · 38 mi |
| Green | 1.3 | 37 ft | Easy | 23 min · 9 mi |
| Deep Woods Trail | 1.1 | 17 ft | Easy | 19 min · 10 mi |
| red trail (Maxwell Hall Natural Resource Management Area) | 1.2 | 35 ft | Easy | 43 min · 27 mi |
| Blue trail (Maxwell Hall Natural Resource Management Area) | 1.9 | 29 ft | Easy | 44 min · 27 mi |
| Yellow | 1.6 | 22 ft | Easy | 19 min · 9 mi |
Lakes: St Marys Lake Trail to Saint Marys Lake; White Trail (Saint Mary's River State Park) to Saint Marys Lake; Woodland Creek Trail to Richardsons Pond; Swamp And Plantation Trails to Cedarville Pond
Nearby towns: La Plata (24 mi) · Fredericksburg (46 mi) · Washington (46 mi) · Annapolis (46 mi)
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