About hiking in Windsor County

Windsor County, Vermont has 281 named trails tagged for hiking, covering 243 miles, an average of 0.9 miles each. The longest is Slack Hill Trail, at 9.6 miles. 3 run 5 miles or longer.

What the hiking trails in Windsor County are like

By length, 211 are under a mile, 67 run 1 to 5 miles, and 3 are 5 miles or longer. 15 are loops, ending where they start; the longest is Slack Hill Trail, at 9.6 miles.

Of the 133 with a difficulty rating, 85 easy, 39 moderate, and 9 hard. Of the 281 with measured elevation, Weathersfield Trail climbs the most, about 2,506 ft, and 9 gain 1,000 ft or more.

All 281 hiking trails, longest first

Slack Hill TrailHike9.6 mi Bill Ballard TrailHike6.8 mi Catamount TrailHike6.1 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 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 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 Grassy LaneHikeMTB1.6 mi North Ridge Loop TrailHike1.6 mi Town Highway 67HikeMTB1.5 mi red loopHike1.5 mi CCC TrailHike1.4 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 white river ledges trailHike1.3 mi SAM TrailHike1.3 mi Blue Ribbon ConnectorHikeMTB1.3 mi Round Top RoadHikeMTB1.3 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 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 BroadwayHike1.1 mi McIndoe Farm TrailHikeMTB1.1 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 South Ridge RunHike1.0 mi Vista Trail (Blue)Hike1.0 mi West Side LoopHikeMTB1.0 mi Kents ledge trailHike1.0 mi Schist CreekHike1.0 mi Hay RideHikeMTB1.0 mi Town Highway 21HikeMTB1.0 mi Town Highway 25HikeMTB1.0 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 RidgebackHikeMTB0.9 mi Town Highway 51HikeMTB0.9 mi Upper Turnpike RoadHikeMTB0.9 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 Resevoir trailHike0.8 mi 42nd StreetHikeMTB0.8 mi ContagiousHike0.8 mi Paradise Hill FlowHikeMTB0.8 mi blue trailsHike0.8 mi Boulder DashHikeMTB0.7 mi Class 4 RoadHike0.7 mi TNTHikeMTB0.7 mi Middle Pass TrailHike0.7 mi Southern BelleHike0.7 mi Joshua RoadHikeMTB0.7 mi Governor's TrailHike0.7 mi ZebedeeHike0.7 mi Brown Schoolhouse RoadHike0.7 mi Firetower TrailHike0.7 mi WarmanHike0.7 mi Milton Frye Nature TrailsHike0.7 mi North Peak TrailHike0.7 mi Blue DipperHike0.7 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 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 Rock N' RollHikeMTB0.5 mi Sir BermsalotHike0.5 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 LoopHike0.4 mi Converse LoopHike0.4 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 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 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 Middle Rum StreetHikeMTB0.4 mi StingerHike0.4 mi Hang Glider TrailHike0.4 mi Town Highway 54Hike0.4 mi McKnight TrailHike0.4 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 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 DeerHike0.2 mi Cabin ConnectorHike0.2 mi Cloud 9.9Hike0.2 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 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 Cloud drop connectorHike0.2 mi Spawn ConnectorHike0.2 mi Lakeside TrailHike0.2 mi Cloud Climber 2Hike0.2 mi Cross Cut 1Hike0.2 mi Kickstands UpHike0.2 mi Honest AbeHike0.2 mi Double Creek TrailHike0.2 mi Daisy Lane TrailHikeMTB0.2 mi North Dike PathHikeMTB0.2 mi French Lot TrailHike0.2 mi Forest Canopy WalkwayHike0.2 mi WeaselHike0.2 mi Skinny LinkHike0.2 mi EncoreHike0.2 mi Cross Over TrailHike0.1 mi FiddlerHike0.1 mi Lincoln Street Link TrailHike0.1 mi Futures LinkHike0.1 mi Cross TownHike0.1 mi 1903 RouteHike0.1 mi Quad BypassHikeMTB0.1 mi Poor Farm RoadHike0.1 mi Striaght upHike0.1 mi CoronaryHikeMTB0.1 mi Steam Donkey Cut-OffHike0.1 mi Spring TrailHike0.1 mi Upper Loveland TrailHikeMTB0.1 mi

← All Windsor 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.