Trails Near Woodstock, VT | Trailmonger

About trails near Woodstock, Vermont

56 named trails lie within about 25 miles of Woodstock, covering 38.6 miles in total. 49 of them are tagged for hiking and 1 for mountain biking.

The closest is Ridge Run, about 0.0 miles away. 56 of them lie within 10 miles of town. The longest nearby is Easy Grade, at 3.2 miles. These trails fall in Windsor County.

What the trails near Woodstock are like

By length, 47 are under a mile and 9 run 1 to 5 miles. 1 is a loop, ending where it starts; the longest is Maple Grove Loop Trail, at 0.3 miles.

Of the 44 with a difficulty rating, 33 easy, 6 moderate, and 5 hard. Of the 56 with measured elevation, Faulkner Trail climbs the most, about 952 ft.

All 56 trails, nearest first

Ridge RunWindsor County0.2 mi PegwayHikeWindsor County0.4 mi Skinny LinkHikeWindsor County0.2 mi Stewardship TrailHikeWindsor County0.9 mi Faulkner TrailHikeWindsor County1.4 mi Lower traplineHikeWindsor County0.3 mi Honest AbeHikeWindsor County0.2 mi OverlookHikeWindsor County0.5 mi UpshotHikeWindsor County0.5 mi Skinny DipHikeWindsor County0.6 mi Constant FlowHikeWindsor County0.6 mi Precipice TrailHikeWindsor County0.7 mi James JungleWindsor County0.4 mi Return to send itHikeWindsor County0.3 mi DropoutWindsor County0.2 mi RavineHikeWindsor County0.2 mi Quarry ConnectorWindsor County0.2 mi Mount Peg TrailHikeWindsor County2.7 mi Middle traplineHikeWindsor County0.2 mi Kent's ConnectorHikeWindsor County0.2 mi Nick's NeighborhoodHikeWindsor County1.4 mi Kris KrossHikeWindsor County0.6 mi North Peak TrailHikeWindsor County0.7 mi Upper CrossHikeWindsor County0.3 mi Upper traplineHikeWindsor County0.2 mi Easy grade to TFW linkHikeWindsor County0.5 mi Schist CreekHikeWindsor County1.0 mi Chutes and LaddersWindsor County0.2 mi CharliesHikeWindsor County1.1 mi Outer LoopHikeWindsor County0.2 mi Rolling RockHikeWindsor County0.4 mi Telemark TrailHikeWindsor County0.6 mi Mountain Road Carriage PathHikeWindsor County2.5 mi Billings TrailHikeWindsor County0.3 mi Alder patchHikeWindsor County0.8 mi Express laneHikeWindsor County0.4 mi Ravine TrailHikeWindsor County0.7 mi Striaght upHikeWindsor County0.1 mi Giddy UpHikeMTBWindsor County0.4 mi Easy GradeHikeWindsor County3.2 mi Pogue Brook TrailHikeWindsor County0.7 mi Olin's OxHikeWindsor County0.3 mi One Less Traveled TrailHikeWindsor County1.8 mi Maple Grove Loop TrailHikeWindsor County0.3 mi Through the Hub ConnectorHikeWindsor County0.4 mi The EssHikeWindsor County0.3 mi Trail of the Fallen WomanHikeWindsor County2.6 mi FlatlanderHikeWindsor County0.5 mi Knox Meadow LinkHikeWindsor County0.7 mi Cloud drop connectorHikeWindsor County0.2 mi Red lineHikeWindsor County0.7 mi HardstyleWindsor County0.7 mi Knox Meadow LoopWindsor County1.9 mi Cross TownHikeWindsor County0.1 mi Cloud DropHikeWindsor County0.9 mi Sir BermsalotHikeWindsor County0.5 mi

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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.