Hiking in Windsor County
263 named trails · 655 miles · 58 trailheads
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Trails, best known first
- Long Trail
- Appalachian Trail
- Futures Trail
- Weathersfield Trail
- Windsor Trail
- Faulkner Trail
- North Country National Scenic Trail (VT)
- Slack Hill Trail
- Moose Trek Trail
- Brownsville Trail
- Catamount Trail
- Green Trail
- Blue Ribbon Trail
- Mountain Road Carriage Path
- Summit Trail
- Beacon Hill Loop
- Bill Ballard Trail
- Warman
- Mount Peg Trail
- Fusters
- Hang Glider Trail
- Slab Trail
- Hazen Trail
- Zebedee
- Heyl Trail
- Sand Hill Trail
- Firetower Trail
- Village Trail
- Labyrinth
- Roland's Run
- Spruce Trail
- Bear Climb
- Castle Rock Trail
- red loop
- Bradley Hill Trail
- One Less Traveled Trail
- West Side Loop
- North Peak Trail
- Precipice Trail
- Red Pine Trail
- South Side Trail
- Amity Pond Trail
- Pine Drop
- Blood Rock Trail
- Simonds Way
- Wright Farm Trail
- Billings Trail
- Dog Loop Trail
- Futures Link
- Larch Trail
- North Peak Trail
- P5 Fo Fun
- Pogue Brook Trail
- Precipice Trail
- Quechee Gorge Trail
- Ravine Trail
- white river ledges trail
- Amity Pond Trail
- blue trails
- Bicentennial Trail
- Woody Adams Trail
- Vista Trail (Blue)
- Salt Ash Mountain Trail
- Salt Ash Mountain Trail
- Lower Loop
- Maple Trail
- Steam Donkey Cut-Off
- West Loop
- West Ridge Trail
- Catamount Trail
- CCC Trail
- Twin Peaks Trail
- Plymsbury Wildlife Management Area Trail
- Brown Schoolhouse Road
- Home Again
- Lower Cloud Climber
- Milton Frye Nature Trails
- Prosper Trail
- Red Trail
- Ridge Trail
- Escalator
- Gracie's Loop
- Grassy Lane
- Greendale Trail
- Lynx
- Parcel 5
- Reading Pond Road
- SAM Trail
- Town Highway 21
- Trail of the Fallen Woman
- Upper Cross
- Norcross Trail
- Monument Trail
- Pond Loop
- North Ridge Loop Trail
- Southern Belle
- Stonewall
- Easy Grade
- Kents ledge trail
- Across the Pond Trail
- Backwater Trail
- Blood Brook Trail
- Blue Trail
- Flatlander
- Luvin' It
- McIndoe Farm Trail
- McKnight Trail
- Ottauquechee Trail
- Riverwalk Trail
- Tinker Brook Trail
- Wilderness Trail
- Moose Brook Trail
- Mt Moses Trail
- Pine Twister
- State Forest Highway
- Creek Trail
- Blue Dipper
- Class 4 Road
- Crescent Lake Trail
- Escalator
- Gravel Pit Road
- Hay Ride
- Just Smile
- King Arthur Trail
- King Farm Loop Trail
- Last Mile
- Mile - Long Field
- Pogue Lakeside Trail
- Pond Road
- Ridgeback
- Rock N' Roll
- South Ridge Run
- The Stairs
- Town Highway 51
- Upper Cloud Climber
- Upper Loop
- William Tucker Trail
- Wind Up
- Alder patch
- Ascutney Trail
- Burton Woods Road
- Colby Pond Trail
- Converse Loop
- Juniper Hill Trail
- Middle Pass Trail
- Ridge Trail
- Round Top Road
- State Forest Highway
- Swoops and Loops Trail
- Town Highway 15
- Town Highway 22
- Town Highway 67
- WB Brown Trail
- Mountain View Loop
- Blue Ribbon Connector
- Joshua Road
- Knox Meadow Link
- Paradise Hill Flow
- Acer Loop Trail
- Acer Loop Trail
- Ashes Ashes Trail
- Big Field Road
- Boulder Dash
- Cort's Jester
- Crazy Mazie
- Elm Lot Trail
- Fifth
- Hillibard's trail
- Kilowatt Park Trail
- King Arthur Trail
- Lady Slipper Path
- Last Mile
- Laughlin Trail
- Lingelbach Trail
- Lower Fielder's Choice
- Lower Fifth
- Nature Trail
- Ottauquechee Trail
- Ottauquechee Trail
- Pass the Buck
- Quarry Chase
- Red Pine Trail
- Reservoir path
- Rikert Trail (closed)
- Skinny Dip
- Sluice
- Spline Trail
- Stewardship Trail
- Stump Dump
- Telemark Trail
- The Grassy Knowl
- Upper Broadway
- Upper Noodles
- Woods Road
- Burton Woods Road
- LT4
- Norcross Trail
- Otto Merrill Road
- Salt Ash Road
- Town Highway 25
- Town Highway 26
- Upper Turnpike Road
- Wight Cemetery Road
- Burke Loop
- Cloud 9.9
- Cloud Climber 2
- Cossingham Trail
- Cross Over Trail
- Dole It Out
- Farrar Trail
- Forest Canopy Walkway
- Lingelbach Trail
- Nimbus
- Summit Loop
- Weazel
- Moose Brook Trail
- Bypass
- Back 40 Trail
- Betty Booth Trail
- Blood Hill Trail
- Broadway
- Coronary
- Cross Cut 1
- Crosscut 3
- Dutton Hill
- Dutton Hill
- Ease Up
- Falls From Grace
- Falls From Grace
- Falls Trail
- Governor's Trail
- Green Trail
- Kickstands Up
- Lakeside Trail
- Lower Broadway
- Maple Grove Loop Trail
- Maple Lot Trail
- Middle Road
- Newton Lane
- Oh Deer
- Olin's Ox
- Ottauquechee Trail
- Overlook
- Powers Trail
- Rosemary Littledale Rieser Trail
- Swoops and Loops Trail
- Swoops and Loops Trail
- The Ess
- Town Highway 21
- Town Highway 58
- Weasel
- Winturri Shelter Trail
- Quad Bypass
- Daisy Lane Trail
- Cabin Connector
- CCC Trail Connector
- CCC Trail Connector
- Easy grade to TFW link
- Through the Hub Connector
- Corridor 12
- North Dike Path
- Upper Loveland Trail
- 1903 Route
Parking in Windsor County
Lots with a gold seal are verified. The rest are not yet confirmed.
- Amity Pond Trail Trailhead
- Appalachian Trail Trailhead
- Appalachian Trail Trailhead (Norwich)
- Appalachian Trail Trailhead (Norwich)
- Appalachian Trail Trailhead (Pomfret)
- Appalachian Trail Trailhead (Woodstock)
- Bear Climb Trailhead
- Bill Ballard Trail Trailhead
- Blue Ribbon Trail Trailhead
- Blue Trail Trailhead (Perkinsville)
- Brownsville Trail Trailhead
- C.C.C. Pond Access Area
- Cabin Area Parking
- Cossingham Road Farm Trailhead Parking
- Dog Loop Trail Trailhead
- Faulkner Trail Trailhead
- Firetower Trail Trailhead
- Flatlander Trailhead
- Futures Trail Trailhead
- Grassy Lane Trailhead
- Green Trail Trailhead
- Hazen Trail Trailhead
- Hazen Trail Trailhead (Norwich)
- Hazen Trail Trailhead (Norwich)
- Juniper Hill Trail Trailhead
- Kilowatt Park Trail Trailhead
- King Arthur Trail Trailhead
- King Arthur Trail Trailhead (Norwich)
- King Arthur Trail Trailhead (Norwich)
- Lewiston Lot
- Lingelbach Trail Trailhead
- Lower Cloud Climber Trailhead
- Lower Fielder's Choice Trailhead
- Milton Frye Nature Trails Trailhead
- Moose Brook Trail Trailhead
- Moose Trek Trail Trailhead
- Mountain Road Carriage Path Trailhead
- Nature Trail Trailhead
- Ottauquechee Trail Trailhead
- Parcel 5 Parking
- Pond Loop Trailhead
- Prosper Trail Trailhead
- Quechee Gorge Trail Trailhead
- Quechee Gorge Trail Trailhead (White River Junction)
- Reading Pond Road Trailhead
- Red Trail Trailhead
- Ridge Trail Trailhead
- Riverwalk Trail Trailhead
- Sand Hill Trail Trailhead
- Slack Hill Trail Trailhead
- Spruce Trail Trailhead
- Summit Trail Trailhead
- Tinker Brook Trail Trailhead
- Vista Trail (Blue) Trailhead
- Weathersfield trailhead parking
- white river ledges trail Trailhead
- Wilderness Trail Trailhead
- Windsor Trail