About trails in Windsor County, Vermont

Windsor County has 329 named trails on the map, covering 302 miles in total, an average of 0.9 miles per trail. That is the 2nd largest mapped trail network among 14 counties in Vermont. 282 of them are tagged for hiking and 89 for mountain biking.

The longest single trail is Blue Ribbon Trail, at 11.1 miles. 6 trails run 5 miles or longer. Mapped points of interest in the county include 8 trailheads, 20 campsites, 26 waterfalls, 22 boat launches, and 2 rapids. The nearest towns to these trails are Woodstock, West Woodstock, and Ascutney.

What the trails in Windsor County are like

By length, 239 are under a mile, 79 run 1 to 5 miles, and 6 are 5 miles or longer. 16 are loops, ending where they start; the longest is Blue Ribbon Trail, at 11.1 miles.

Every one carries a difficulty rating: 65 easy, 235 moderate, and 24 hard. Of the 324 with measured elevation, Windsor Trail climbs the most, about 2,569 ft, and 13 gain 1,000 ft or more.

Explore by activity

329All trails

282Hiking 89Mountain biking

302Total miles

20Campsites

22Boat launches

26Waterfalls

8Trailheads

2Rapids

Blue Ribbon TrailMTB11.1 mi Slack Hill TrailHike9.6 mi Toonerville TrailMTB7.1 mi Bill Ballard TrailHike6.8 mi Catamount TrailHike6.1 mi Upper Valley Loop TrailMTB5.3 mi Norcross TrailHikeMTB4.4 mi Mt Moses TrailHikeMTB4.2 mi State Forest HighwayHikeMTB4.2 mi Salt Ash Mountain TrailHike4.0 mi Futures TrailHike3.9 mi Hazen TrailHike3.9 mi Tunnel RidgeMTB3.8 mi FustersHike3.6 mi Town Highway 15HikeMTB3.3 mi Parcel 5HikeMTB3.2 mi Easy GradeHike3.2 mi Swoops and Loops TrailHikeMTB2.7 mi Mount Peg TrailHike2.7 mi Trail of the Fallen WomanHike2.6 mi Reading Pond RoadHikeMTB2.5 mi Weathersfield TrailHike2.5 mi Mountain Road Carriage PathHike2.5 mi Amity Pond TrailHike2.4 mi Windsor TrailHike2.4 mi Brownsville TrailHike2.3 mi Bicentennial TrailHike2.3 mi West LoopHike2.0 mi Burton Woods RoadHikeMTB2.0 mi Knox Meadow Loop1.9 mi Moose Trek TrailHike1.8 mi Maple TrailHike1.8 mi One Less Traveled TrailHike1.8 mi Sand Hill TrailHikeMTB1.7 mi Acer Loop TrailHike1.7 mi Bear ClimbHike1.7 mi Sap BoilerMTB1.7 mi Grassy LaneHikeMTB1.6 mi Creamery RunMTB1.6 mi North Ridge Loop TrailHike1.6 mi Town Highway 67HikeMTB1.5 mi red loopHike1.5 mi CCC TrailHike1.4 mi Rich Trail1.4 mi Faulkner TrailHike1.4 mi Town Highway 22HikeMTB1.4 mi Pogue Lakeside TrailHike1.4 mi Quechee Gorge TrailHike1.4 mi Slash RidgeHike1.4 mi LynxHike1.4 mi Pond RoadHike1.4 mi Nick's NeighborhoodHike1.4 mi King Farm Loop TrailHike1.4 mi Swan DiveMTB1.4 mi white river ledges trailHike1.4 mi SAM TrailHike1.3 mi Blue Ribbon ConnectorHikeMTB1.3 mi Round Top RoadHikeMTB1.3 mi Cassidy's ChaseMTB1.3 mi Mount Tom Carriage Road PathHike1.3 mi Greendale TrailHike1.3 mi Beacon Hill LoopHike1.2 mi P5 Fo FunHike1.2 mi Last MileHikeMTB1.2 mi Walker Trail1.2 mi Heyl TrailHike1.2 mi Green TrailHikeMTB1.2 mi Red Pine TrailHike1.2 mi West Ridge TrailHike1.1 mi EscalatorHike1.1 mi Prosper TrailHike1.1 mi Gracie's LoopHike1.1 mi Old Gents (up)MTB1.1 mi BroadwayHike1.1 mi McIndoe Farm TrailHikeMTB1.1 mi Bobo LinkMTB1.1 mi CharliesHike1.1 mi Colby Pond TrailHikeMTB1.1 mi Luvin' ItHikeMTB1.1 mi Dog Loop TrailHike1.1 mi Ottauquechee TrailHike1.0 mi Lower LoopHike1.0 mi Ridge TrailHike1.0 mi AtlasMTB1.0 mi Randolph Gap TrailMTB1.0 mi South Ridge RunHike1.0 mi Vista Trail (Blue)Hike1.0 mi West Side LoopHikeMTB1.0 mi Kents ledge trailHike1.0 mi Dothan Brook School Walk and Ride Path1.0 mi Schist CreekHike1.0 mi Hay RideHikeMTB1.0 mi Town Highway 21HikeMTB1.0 mi SpreaderMTB1.0 mi Earl's TrailMTB1.0 mi Town Highway 25HikeMTB1.0 mi Reading Pond Trail0.9 mi Red TrailHike0.9 mi Cloud DropHike0.9 mi WB Brown TrailHikeMTB0.9 mi CoasterHike0.9 mi Otto Merrill RoadHikeMTB0.9 mi Stewardship TrailHike0.9 mi RidgebackHikeMTB0.8 mi Town Highway 51HikeMTB0.8 mi Upper Turnpike RoadHikeMTB0.8 mi Ashes Ashes TrailHike0.8 mi Village TrailHikeMTB0.8 mi Town Farm RoadHike0.8 mi Elm Lot TrailHike0.8 mi StonewallHikeMTB0.8 mi Alder patchHike0.8 mi King Arthur TrailHikeMTB0.8 mi Larch TrailHike0.8 mi Gravel Pit RoadHikeMTB0.8 mi Appalachian National Scenic Trail0.8 mi Resevoir trailHike0.8 mi 42nd StreetHikeMTB0.8 mi ContagiousHike0.8 mi Paradise Hill FlowHikeMTB0.8 mi blue trailsHike0.8 mi Boulder DashHikeMTB0.7 mi Chase 4 Corners Trail0.7 mi Class 4 RoadHike0.7 mi TNTHikeMTB0.7 mi Middle Pass TrailHike0.7 mi Rube's RunMTB0.7 mi Southern BelleHike0.7 mi Joshua RoadHikeMTB0.7 mi Governor's TrailHike0.7 mi ZebedeeHike0.7 mi Brown Schoolhouse RoadHike0.7 mi Hardstyle0.7 mi Firetower TrailHike0.7 mi WarmanHike0.7 mi Bobsled Trail0.7 mi Milton Frye Nature TrailsHike0.7 mi North Peak TrailHike0.7 mi Blue DipperHike0.7 mi Bailey Hill Trail0.7 mi Pogue Brook TrailHike0.7 mi Red lineHike0.7 mi Ravine TrailHike0.7 mi Knox Meadow LinkHike0.7 mi Precipice TrailHike0.7 mi Crescent Lake TrailHike0.7 mi Telemark TrailHike0.6 mi Lower Cloud ClimberHike0.6 mi LT4HikeMTB0.6 mi Kris KrossHike0.6 mi Pine TwisterHikeMTB0.6 mi Moose Brook TrailHikeMTB0.6 mi Pine DropHike0.6 mi Upper Sawn of VaughanHike0.6 mi Constant FlowHike0.6 mi Bradley Hill TrailHike0.6 mi Chantrea HillMTB0.6 mi Mile - Long FieldHike0.6 mi Upper LoopHike0.6 mi William Tucker TrailHike0.6 mi Wind UpHikeMTB0.6 mi Skinny DipHike0.6 mi Just SmileHike0.5 mi Wight Cemetery RoadHikeMTB0.5 mi Old Gents (down)MTB0.5 mi Rock N' RollHikeMTB0.5 mi Sir BermsalotHike0.5 mi Valley of the FernsMTB0.5 mi UpshotHike0.5 mi Town Highway 26HikeMTB0.5 mi FlatlanderHike0.5 mi Upper Cloud ClimberHike0.5 mi Lena's LandingHike0.5 mi Home AgainHikeMTB0.5 mi Riverwalk TrailHike0.5 mi Monument TrailHike0.5 mi Woods RoadHike0.5 mi Burke LoopHikeMTB0.5 mi Easy grade to TFW linkHike0.5 mi OverlookHike0.5 mi Pond LoopHike0.5 mi Converse LoopHike0.5 mi Lou's LoopMTB0.4 mi Marsh Brook ConnectorMTB0.4 mi Lower BroadwayHike0.4 mi Rolling RockHike0.4 mi Blue TrailHike0.4 mi Cort's JesterHike0.4 mi Spline TrailHike0.4 mi Rikert Trail (closed)Hike0.4 mi Falls From GraceHike0.4 mi Upper NoodlesHike0.4 mi Middle RoadHikeMTB0.4 mi Simonds WayHikeMTB0.4 mi Buffer ZoneHike0.4 mi Cossingham TrailHike0.4 mi Express laneHike0.4 mi PegwayHike0.4 mi (not maintained)Hike0.4 mi Mountain View LoopHikeMTB0.4 mi James Jungle0.4 mi Backwater TrailHike0.4 mi Through the Hub ConnectorHike0.4 mi ShooterHike0.4 mi Lower Spawn of VaughanHike0.4 mi Wilderness TrailHike0.4 mi Across the Pond TrailHike0.4 mi Chantrea FieldMTB0.4 mi Giddy UpHikeMTB0.4 mi Tilden Hill RoadHike0.4 mi Creek TrailHike0.4 mi Lower Rum StreetHikeMTB0.4 mi Summit TrailHike0.4 mi Town Highway 58HikeMTB0.4 mi Tower TrailMTB0.4 mi Middle Rum StreetHikeMTB0.4 mi StingerHike0.4 mi Hang Glider TrailHike0.4 mi Town Highway 54Hike0.4 mi McKnight TrailHike0.3 mi Blood Brook TrailHike0.3 mi Reservoir pathHike0.3 mi Blood Hill TrailHikeMTB0.3 mi Maple Grove Loop TrailHike0.3 mi LabyrinthHike0.3 mi SluiceHike0.3 mi Upper BroadwayHike0.3 mi The Grassy KnowlHike0.3 mi Powers TrailHikeMTB0.3 mi Big Field RoadHike0.3 mi Stump DumpHike0.3 mi Newton LaneHikeMTB0.3 mi Roland's RunHike0.3 mi Woody Adams TrailHikeMTB0.3 mi Slab TrailHike0.3 mi PennisulaHike0.3 mi Wright Farm TrailHikeMTB0.3 mi Lower traplineHike0.3 mi Olin's OxHike0.3 mi The EssHike0.3 mi Dutton HillHike0.3 mi Upper CrossHike0.3 mi DynomiteHike0.3 mi Quarry ChaseHike0.3 mi Return to send itHike0.3 mi Lingelbach TrailHike0.3 mi Pass the BuckHike0.3 mi Upper Rum StreetHike0.3 mi CCC Trail ConnectorHike0.3 mi Lady Slipper PathHike0.3 mi Lower FifthHike0.3 mi Legal Trail 40.3 mi FifthHike0.3 mi Maple Lot TrailHike0.3 mi Tinker Brook TrailHike0.3 mi Spruce TrailHike0.3 mi Juniper Hill TrailHike0.3 mi Billings TrailHike0.3 mi Ascutney TrailHike0.3 mi Hillibard's trailHike0.3 mi South Side TrailHike0.3 mi Oh DeerHike0.3 mi Cabin ConnectorHike0.3 mi Cloud 9.9Hike0.3 mi WeazelHike0.2 mi Corridor 12HikeMTB0.2 mi Outer LoopHike0.2 mi Farrar TrailHike0.2 mi Rosemary Littledale Rieser TrailHike0.2 mi Blood Rock TrailHike0.2 mi Kent's ConnectorHike0.2 mi Dole It OutHike0.2 mi Laughlin TrailHike0.2 mi Kilowatt Park TrailHike0.2 mi Highland Ave TrailHike0.2 mi Summit LoopHike0.2 mi NimbusHike0.2 mi Upper traplineHike0.2 mi Drop into the Meadow0.2 mi Ease UpHike0.2 mi Castle Rock TrailHike0.2 mi Falls TrailHike0.2 mi RavineHike0.2 mi Back 40 TrailHike0.2 mi Lower Fielder's ChoiceHikeMTB0.2 mi Reservoir ConnectorHike0.2 mi Middle traplineHike0.2 mi Betty Booth TrailHike0.2 mi Big DogMTB0.2 mi Ridge Run0.2 mi Cloud drop connectorHike0.2 mi Chutes and Ladders0.2 mi Spawn ConnectorHike0.2 mi Lakeside TrailHike0.2 mi Cloud Climber 2Hike0.2 mi Cross Cut 1Hike0.2 mi Kickstands UpHike0.2 mi Quarry Connector0.2 mi Honest AbeHike0.2 mi Double Creek TrailHike0.2 mi

Trails by town in Windsor 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.