About hiking in Bennington County

Bennington County, Vermont has 150 named trails tagged for hiking, covering 221 miles, an average of 1.5 miles each. The longest is Appalachian Trail;Long Trail, at 43.2 miles. 8 run 5 miles or longer.

What the hiking trails in Bennington County are like

By length, 99 are under a mile, 43 run 1 to 5 miles, and 8 are 5 miles or longer. 4 are loops, ending where they start; the longest is Lunch (bike), at 1.7 miles.

Of the 63 with a difficulty rating, 26 easy, 25 moderate, and 12 hard. Of the 148 with measured elevation, Appalachian Trail;Long Trail climbs the most, about 12,495 ft, and 13 gain 1,000 ft or more.

All 150 hiking trails, longest first

Appalachian Trail;Long TrailHike43.2 mi Catamount TrailHike7.6 mi West Ridge TrailHike7.5 mi Branch Pond TrailHike7.4 mi Appalachian Trail; Long TrailHike7.1 mi Lye Brook TrailHike7.0 mi Castle Brook RoadHikeMTB6.1 mi Bald Mountain TrailHike5.3 mi Little Pond RoadHikeMTB4.3 mi Old Town RoadHike3.7 mi Broad Brook TrailHike3.6 mi East Dorset TrailHike3.3 mi Flood Dam TrailHike2.8 mi Masters Mtn TrailHike2.7 mi Summit Trail (Blue)Hike2.6 mi Mountain trailHike2.5 mi Dyke (Downhill Only)Hike2.4 mi Historic Marble Rail TrailHikeMTB2.3 mi Vista TrailHike2.3 mi Woodford TrailHike2.2 mi Forest Road 268Hike2.1 mi Griffith Lake TrailHike2.0 mi Robert Frost TrailHike2.0 mi Forest Road 373HikeMTB1.9 mi Lodge RoadHike1.9 mi Sidehill Wampus (bike)HikeMTB1.8 mi Dome TrailHikeMTB1.7 mi Lunch (bike)HikeMTB1.7 mi Mount Bluff Traili (White)Hike1.6 mi Halloween TreeHikeMTB1.5 mi Maidenhair Trail (Orange)Hike1.5 mi Corridor 9 TrailHike1.5 mi Old Rootville RoadHike1.5 mi LongshotHike1.4 mi Stagecoach RoadHikeMTB1.4 mi Jones Brook TrailHike1.4 mi PEW trailHike1.3 mi Lower BeaconHikeMTB1.3 mi Danish DelightHike1.2 mi Hatch TrailHike1.2 mi Trillium Trail (Green)Hike1.2 mi ChicadeeHike1.1 mi Meadow TrailHike1.1 mi BoomerangHike1.1 mi Lightfoot Camp RoadHike1.1 mi WorkoutHike1.1 mi Summit TrailHike1.0 mi WoodpeckerHike1.0 mi Hops & VinesHikeMTB1.0 mi East Branch TrailHike1.0 mi Shea's rebellionHike1.0 mi Maple Creemee (bike)HikeMTB1.0 mi Hawley Mountain RoadHike1.0 mi HawthornHike1.0 mi Wildlife TrailHike1.0 mi Kouwenhoven RdHike0.9 mi duke's loopHike0.9 mi Yankee DoodleHike0.9 mi McCormick TrailHike0.9 mi Zaphod's RunHikeMTB0.9 mi Grime's GrindHikeMTB0.8 mi Beebe Pond TrailHike0.8 mi Gilberts Lookout (Blue)Hike0.8 mi Forest Road 376HikeMTB0.8 mi Dome Summit TrailHike0.8 mi Mountain DewHikeMTB0.8 mi VRS (VTR) former Rutland RailroadHikeMTB0.8 mi CatamountHike0.7 mi Gettysberm (bike)HikeMTB0.7 mi Dorset Hollow TrailHike0.7 mi Forest Road 272HikeMTB0.7 mi SVAC Loop (Orange Black Stripe)Hike0.7 mi Jacob's LadderHikeMTB0.7 mi Hoosac Tunnel and Wilmington RailroadHike0.7 mi Lourie TrailHike0.7 mi WhistlepigHike0.7 mi Jackson's CrossingHike0.7 mi Pond Loop (White Green)Hike0.7 mi Lake TrailHike0.7 mi Beaver pond loopHike0.7 mi Maple TrailHike0.7 mi Lift LineHike0.7 mi Everett Cave TrailHike0.7 mi Link to Little PondHike0.6 mi Gettysburg Alternative (Yellow)Hike0.6 mi Barton TrailHike0.6 mi Discovery TrailHike0.6 mi OvergrownHike0.6 mi Snail TrailHikeMTB0.6 mi TBN Downhill (bike)HikeMTB0.6 mi skin trackHike0.6 mi Owls Head Loop (Red)Hike0.6 mi Troll RoadHike0.6 mi Green ManHikeMTB0.6 mi Agawon TrailHike0.6 mi Dutch MeadowsHike0.5 mi Siviculture TrailHike0.5 mi Upper TrailHike0.5 mi TBN Traverse (bike)HikeMTB0.5 mi Oak LoopHike0.5 mi Hoosic Bend TrailHike0.5 mi Flatlander's PassHike0.5 mi Trout Lily Trail (White Purple)Hike0.5 mi Loose MooseHike0.5 mi Carriage Road TrailHike0.5 mi Ursa WayHikeMTB0.5 mi Red Gate TrailHike0.5 mi Farm TrailHike0.5 mi Trail To Area CHike0.4 mi E-Z wayHike0.4 mi SlingshotHike0.4 mi Lower Prince Quarry Loop (Orange)Hike0.4 mi Lye Brook Falls TrailHike0.4 mi Initial RockHikeMTB0.4 mi Farm LoopHike0.4 mi Hobbit HollowHike0.4 mi Branch Pond Connector TrailHike0.4 mi Viewpt TrailHike0.4 mi The GrottoHikeMTB0.4 mi Ski TrailHike0.4 mi Snicket (Orange Black Stripe)Hike0.4 mi Coach RoadHikeMTB0.4 mi Rich Woods TrailHike0.4 mi Old Harriman Station DriveHike0.4 mi Gettysburg Quarry (Blue)Hike0.4 mi Flat TireHikeMTB0.4 mi unmaintainedHike0.3 mi Running BearHikeMTB0.3 mi North RoadHike0.3 mi This WayHike0.3 mi Hill 2290Hike0.3 mi Hay Field TrailHike0.3 mi X-mas TreeHike0.3 mi Entrance (Green)Hike0.3 mi Atwood LoopHike0.2 mi Three FieldsHikeMTB0.2 mi Delaware and Hudson Railway Washington BranchHike0.2 mi Mo-JoeHike0.2 mi SteffenHike0.2 mi Mansion TrailHike0.2 mi Singletrack ConnectorHikeMTB0.2 mi Stone Place TrailHike0.2 mi Battenkill TrailHike0.2 mi Sawmill RoadHikeMTB0.2 mi Robin's Look Out (Green Black Bar)Hike0.2 mi Everett BallcourtHikeMTB0.2 mi Klondike Quarry (Blue)Hike0.2 mi Cedar Rock TrailHike0.2 mi Groms Way (bike)HikeMTB0.1 mi Trail To Area BHike0.1 mi

← All Bennington 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 October 4, 2026.