About trails in Windham County, Vermont

Windham County has 192 named trails on the map, covering 233 miles in total, an average of 1.2 miles per trail. That is the 7th largest mapped trail network among 14 counties in Vermont. 149 of them are tagged for hiking and 38 for mountain biking.

The longest single trail is West River Trail, at 30.3 miles. 7 trails run 5 miles or longer. Mapped points of interest in the county include 8 trailheads, 18 campsites, 17 waterfalls, and 21 boat launches. The nearest towns to these trails are Stratton Mountain, Chimney Hill, and Putney.

What the trails in Windham County are like

By length, 130 are under a mile, 54 run 1 to 5 miles, and 7 are 5 miles or longer. 1 is a loop, ending where it starts; the longest is Little Hogback Loop, at 0.6 miles.

Every one carries a difficulty rating: 71 easy, 108 moderate, and 12 hard. Of the 188 with measured elevation, Appalachian Trail; Long Trail climbs the most, about 2,088 ft, and 10 gain 1,000 ft or more.

Explore by activity

233Total miles

18Campsites

21Boat launches

17Waterfalls

8Trailheads

West River TrailMTB30.3 mi 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 Trail Forest OneMTB1.8 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 Town Trail1.4 mi Ground Control - Uphill OnlyMTB1.4 mi Legal Trail 41.4 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 Paper RouteMTB1.3 mi Bear's DenMTB1.2 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 TrailHike1.1 mi Hamilton Falls TrailHike1.1 mi Radford-Smith TrailHike1.1 mi White's LoopHike1.1 mi Gulf RoadHikeMTB1.1 mi Ravine TrailHike1.1 mi Race Loop1.1 mi Crosstown TrailHikeMTB1.0 mi Dunn Nature TrailHike1.0 mi Bears Crossing Ski Home Trail1.0 mi Bermie SandersMTB1.0 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 Loam SharkMTB0.9 mi Smith Woods RoadHike0.9 mi Ashworth RoadHikeMTB0.9 mi Ice PondHike0.9 mi Beginner Wanderer Summit Ascent/ Intermediate Summit Meadows AscentHike0.8 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 Low Traverse0.8 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 CrusherMTB0.7 mi Parsons CutoffHike0.7 mi Connector to Timber Ridge >>>Hike0.6 mi Little Hogback LoopHike0.6 mi Ober Hill RoadHike0.6 mi South Pond Loop Winter Crossing0.6 mi Beginner Main Base to Sun Bowl/ Intermediate Lower Mountain LoopHike0.6 mi Short StrawMTB0.6 mi Double BirchHike0.6 mi French RoadHikeMTB0.6 mi South Pond Loop Land Route0.6 mi Three BridgesHike0.6 mi Upper WoodlandsHike0.6 mi The Inn Trail0.6 mi Legal Trail0.6 mi Bobcat RunHike0.6 mi Wide OpenMTB0.6 mi Tunnel Trail0.6 mi Intermediate Summit Meadows AscentHike0.6 mi SwitchbackHike0.5 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 Fox TrotMTB0.5 mi Bear Hill RoadHikeMTB0.5 mi Clinton Bond Trail0.5 mi Beginner Lower Mountain Loop/ Intermediate Lower Mountain Loop/ Intermediate Summit Meadows AscentHike0.5 mi High Road TrailHike0.5 mi Lunch PadMTB0.5 mi Westl River Trail0.5 mi Lower WoodlandsHike0.5 mi Tower TrailHike0.5 mi Bishop TrailHike0.5 mi High Traverse0.5 mi <<< Connector to Magic MountainHike0.4 mi Bear ClawHike0.4 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 Garden GnomesMTB0.4 mi Turner Trail0.4 mi Cottage RoadHike0.4 mi Princess PineHike0.4 mi Undercliff TrailHike0.3 mi Lathrop LaneHike0.3 mi Grizzly AccessMTB0.3 mi SweetHike0.3 mi Just For FunHike0.3 mi RoundaboutHike0.3 mi Alpine Loop0.3 mi Spruced upHike0.3 mi GravitasMTB0.3 mi Private TrailHike0.3 mi North OverlookHike0.3 mi MittensMTB0.3 mi Cross Mountain TrailHike0.3 mi Corn Mill CrossingHike0.3 mi Tower Trail (white)Hike0.3 mi Town Trail Connector0.3 mi T-Bar Trail0.3 mi Fern GullyMTB0.3 mi Tripping Field Access TrailHike0.3 mi Cannonball RunMTB0.2 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 Maybe LaterMTB0.2 mi Buster's Trail0.2 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 Wind DelayMTB0.2 mi Kick StartMTB0.2 mi Angel Falls Extention TrailHike0.2 mi Melchen RoadHikeMTB0.2 mi South OverlookHike0.2 mi Saxtons River Valley TrailHike0.1 mi Stratton View Tenting AccessHike0.1 mi Long WalkHike0.1 mi Labrynth TrailHike0.1 mi Halladay Brook RoadHikeMTB0.1 mi First ImpressionsMTB0.1 mi School TrailHike0.1 mi Stratton Pond SpurHike0.1 mi The ConnectorHike0.1 mi Middle EarthHike0.1 mi Fast GrassMTB0.1 mi Return to SenderMTB0.1 mi Flame TrailHike0.1 mi

Trails by town in Windham County

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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 25, 2026.