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Best trails in Woodstock

749 Reviews
Looking for a great trail near Woodstock, Vermont? AllTrails has 10 great hiking trails, trail running trails, forest trails and more, with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers, and nature lovers like you. If you're looking for the best trails around Pillsbury State Park or Giffords Woods State Forest Park, we've got you covered. You'll also find some great local park options, like Ascutney State Park or Colburn Park. Ready for some activity? There are 7 moderate trails in Woodstock ranging from 1.6 to 4.8 miles and from 692 to 1,345 feet above sea level. Start checking them out and you'll be out on the trail in no time!
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Map of trails in Woodstock
Top trails (10)
#1 - The Pogue and Mount Tom Trail
Marsh-Billings-Rockefeller National Historical Park
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(260)
Length: 4.2 mi • Est. 2 h 8 m
#2 - Faulkner Trail
Marsh-Billings-Rockefeller National Historical Park
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(125)
Length: 2.5 mi • Est. 1 h 22 m
#3 - Mount Tom via Faulkner Trail
Marsh-Billings-Rockefeller National Historical Park
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(84)
Length: 4.2 mi • Est. 2 h 9 m
#4 - Mount Peg Loop
Marsh-Billings-Rockefeller National Historical Park
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(51)
Length: 1.6 mi • Est. 55 m
#5 - The Pogue Loop from Prosper Road
Woodstock, Vermont
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(19)
Length: 2.5 mi • Est. 1 h 15 m
This trail starts on Prosper Road and continues up to The Pogue. If you're looking to continue on to Mount Tom, please search AllTrails for "The Pogue and Mount Tom from Prosper Road".Show more
#6 - The Pogue and Mount Tom from Prosper Road
Woodstock, Vermont
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(17)
Length: 4.8 mi • Est. 2 h 24 m
This trail starts at Prosper Road and continues up past the Pogue towards Mount Tom. This is a popular snowshoeing and cross-country skiing area. If you're looking for the trail solely to the Pogue, please search AllTrails for "The Pogue Loop from Prosper Road".Show more
#7 - Eshqua Bog Natural Area
Eshqua Bog Preserve
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(18)
Length: 0.5 mi • Est. 14 m
Eshqua Bog is a botanical wonderland of cold-climate holdovers--small pockets of bog plant species and a two acre fen--from the post-glacial era 10,000 years ago. This preserve contains a diverse array of bog and fen plants: labrador tea, cotton grass, pitcher plants, showy lady's slippers, larches and buckbean. In springtime, this tiny 40.8-acre preserve, circling the mere speck of an 8-acre bog, bursts forth with color, texture, shapes and scents. Most stunning are the wild orchids. Hundreds of showy lady’s slippers, along with lesser populations of small yellow lady’s slippers, dot the wetland. The somewhat more common pink lady’s slipper abounds here too, along with the northern green orchids and white bog orchids.Show more
#8 - Mount Peg Foot and Bridle Trails
Marsh-Billings-Rockefeller National Historical Park
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(22)
Length: 1.7 mi • Est. 55 m
#9 - Luce's Lookout [PRIVATE PROPERTY]
Green Mountain National Forest
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(121)
Length: 2.5 mi • Est. 1 h 24 m
NOTE: This trail is privately owned and maintained by the landowner. Please be respectful and courteous when hiking this trail. Pack in and out trash! If the road to the trail is full of cars, please find elsewhere to hike. Do not block or turn around in driveways along the road.Show more
#10 - Shackleton Loop
Woodstock, Vermont
easyGray StarGray StarGray StarGray StarGray StarGray StarGray StarGray StarGray StarGray Star
Length: 0.8 mi • Est. 26 m