About hiking in Windham County

Windham County, Vermont has 149 named trails tagged for hiking, covering 177 miles, an average of 1.2 miles each. The longest is Catamount Trail Section 4, at 9.9 miles. 6 run 5 miles or longer.

What the hiking trails in Windham County are like

By length, 96 are under a mile, 47 run 1 to 5 miles, and 6 are 5 miles or longer. 1 is a loop, ending where it starts; the longest is Little Hogback Loop, at 0.6 miles.

Of the 149 with measured elevation, Appalachian Trail; Long Trail climbs the most, about 1,770 ft, and 6 gain 1,000 ft or more.

All 149 hiking trails, longest first

Catamount Trail Section 4Hike9.9 mi South Pond LoopHike9.3 mi East TrailHike6.6 mi Appalachian Trail; Long TrailHike6.5 mi Valley TrailHike6.1 mi IP RoadHike5.1 mi Pond LoopHike5.0 mi West TrailHike4.1 mi North Brookwood TrailHike4.1 mi Ridgeline TrailHike3.9 mi Deerfield Ridge TrailHike3.7 mi Stratton Pond TrailHike3.6 mi Hemlock TrailHike3.3 mi Whites Road to West Lake RoadHike2.7 mi West Cliff TrailHike2.6 mi Haystack Mountain TrailHike2.0 mi Jamie Latham TrailHike2.0 mi Catamount TrailHike2.0 mi West River Trail.HikeMTB1.9 mi Hoot Toot & Whistle TrailHike1.9 mi Deer Run TrailHike1.8 mi Little John TrailHike1.7 mi Hilltop TrailHike1.7 mi Intermediate Woods AscentHike1.7 mi Bemis Hill TrailHike1.7 mi Forest Road 383Hike1.7 mi Townline TrailHike1.6 mi Mount Olga TrailHike1.5 mi Ho Chi Minh TrailHike1.5 mi Beaver Pond LoopHike1.5 mi Dine TrailHike1.5 mi Camp TrailHike1.4 mi Ledges overlook trailHike1.4 mi Holden TrailHike1.3 mi Flood Dam RoadHikeMTB1.3 mi Beginner Wanderer Summit AscentHike1.3 mi Overlook TrailHike1.3 mi North TrailHike1.3 mi Cascade TrailHike1.3 mi Logging Camp TrailHike1.3 mi Hannum TrailHike1.2 mi Intermediate Lower Mountain LoopHike1.2 mi Josh RoadHikeMTB1.2 mi Raponda Ridge TrailHike1.2 mi Shearer Hill TrailHike1.2 mi Windmill Hill TrailHike1.2 mi Bare Hill TrailHike1.2 mi Hamilton Falls TrailHike1.1 mi Radford-Smith TrailHike1.1 mi White's LoopHike1.1 mi Gulf RoadHikeMTB1.1 mi Ravine TrailHike1.1 mi Crosstown TrailHikeMTB1.0 mi Dunn Nature TrailHike1.0 mi Play NiceHikeMTB0.9 mi Hathaway TrailHike0.9 mi Ware Road ConnectorHike0.9 mi Rice Hill TrailHike0.9 mi Beginner Main Base to Sun BowlHike0.9 mi Smith Woods RoadHike0.9 mi Ashworth RoadHikeMTB0.9 mi Ice PondHike0.9 mi Beginner Wanderer Summit Ascent/ Intermediate Summit Meadows AscentHike0.9 mi Grout Pond - Somerset ReservoirHike0.8 mi MorningsideHike0.8 mi Main TrailHike0.8 mi Forest Road 324HikeMTB0.8 mi Douglas TrailHike0.8 mi Ridge TrailHike0.8 mi Athens Access PathHike0.8 mi Connector from Magic Mountain >>>Hike0.8 mi Old Judd RoadHike0.8 mi Headwaters TrailHike0.7 mi Rim RunHike0.7 mi V.A.S.T TrailHike0.7 mi Hinton TailHike0.7 mi Stratton Ridge TrailHike0.7 mi Advanced Summit Standard AscentHike0.7 mi Parsons CutoffHike0.6 mi Connector to Timber Ridge >>>Hike0.6 mi Little Hogback LoopHike0.6 mi Ober Hill RoadHike0.6 mi Beginner Main Base to Sun Bowl/ Intermediate Lower Mountain LoopHike0.6 mi Double BirchHike0.6 mi French RoadHikeMTB0.6 mi Three BridgesHike0.6 mi Upper WoodlandsHike0.6 mi Bobcat RunHike0.6 mi Intermediate Summit Meadows AscentHike0.5 mi Prospect Hill TrailHike0.5 mi Bellows Falls Riverfront TrailHike0.5 mi Ed Dodd TrailHike0.5 mi Sherwood Forest TrailHike0.5 mi <<< Connector from Timber RidgeHike0.5 mi Bear Hill RoadHikeMTB0.5 mi SwitchbackHike0.5 mi Beginner Lower Mountain Loop/ Intermediate Lower Mountain Loop/ Intermediate Summit Meadows AscentHike0.5 mi High Road TrailHike0.5 mi Lower WoodlandsHike0.5 mi Tower TrailHike0.5 mi Bishop TrailHike0.5 mi <<< Connector to Magic MountainHike0.4 mi BearclawHike0.4 mi Porcupine LedgeHike0.4 mi Shoulder TrailHike0.4 mi TRAIL ---NOT A THRU ROAD--- TRAILHike0.4 mi Earle Farm RoadHike0.4 mi Beginner Lower Mountain LoopHike0.4 mi Cliff TrailHike0.4 mi Hogback Summit TrailHike0.4 mi Owl RidgeHike0.4 mi Cottage RoadHike0.4 mi Princess PineHike0.4 mi Undercliff TrailHike0.3 mi Lathrop LaneHike0.3 mi SweetHike0.3 mi Just For FunHike0.3 mi RoundaboutHike0.3 mi Spruced upHike0.3 mi Private TrailHike0.3 mi North OverlookHike0.3 mi Cross Mountain TrailHike0.3 mi Corn Mill CrossingHike0.3 mi Tower Trail (white)Hike0.3 mi Tripping Field Access TrailHike0.2 mi SugarhouseHike0.2 mi Old Tavern TrailHike0.2 mi Spruce LoopHikeMTB0.2 mi Grade AHike0.2 mi The Way InHike0.2 mi Bemis Hill RoadHike0.2 mi Beginner Wanderer Summit Ascent/ Intermediate Woods AscentHike0.2 mi Beginner Lower Mountain Loop/ Intermediate Woods AscentHike0.2 mi Frog HighwayHike0.2 mi Sap BucketHikeMTB0.2 mi Sylvan ParkHike0.2 mi Angel Falls Extention TrailHike0.2 mi Melchen RoadHikeMTB0.2 mi South OverlookHike0.2 mi Saxtons River Valley TrailHike0.2 mi Stratton View Tenting AccessHike0.1 mi Long WalkHike0.1 mi Labrynth TrailHike0.1 mi Halladay Brook RoadHikeMTB0.1 mi School TrailHike0.1 mi Stratton Pond SpurHike0.1 mi The ConnectorHike0.1 mi Middle EarthHike0.1 mi Flame TrailHike0.1 mi

← All Windham County trails

Trail geometry from OpenStreetMap contributors, licensed ODbL. Elevation from the USGS 3D Elevation Program. Compiled and published by Trailmonger · trail data last rebuilt September 24, 2026.