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Best trails in Bennington

765 Reviews
Looking for a great trail near Bennington, Vermont? AllTrails has 13 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 Peebles Island State Park or Moreau Lake State Park, we've got you covered. You'll also find some great local park options, like Mount Greylock State Reservation or Ball Mountain State Recreation Area. Ready for some activity? There are 6 moderate trails in Bennington ranging from 4.3 to 22.6 miles and from 715 to 3,740 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 Bennington
Top trails (13)
#1 - The Long Trail
Green Mountain National Forest
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Length: 272 mi • Est. Multi-day
Vermont’s Long Trail is the oldest long distance hiking trail in the United States. The trail follows the main ridge of the Green Mountains from Massachusetts-Vermont state line to the Canadian border. Novice and expert alike will enjoy the varied terrain of the trail as it passes through the heart of Vermont. For more information visit: https://www.greenmountainclub.org/the-long-trail/Show more
#2 - Bald Mountain
Green Mountain National Forest
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(156)
Length: 7.9 mi • Est. 4 h 39 m
#3 - Harmon Hill via Long Trail (Appalachian Trail)
Green Mountain National Forest
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Length: 3.3 mi • Est. 2 h 5 m
#4 - Woodford Trail
Green Mountain National Forest
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(99)
Length: 2.4 mi • Est. 1 h 7 m
#5 - Bald Mountain
Glastenbury Wilderness
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(73)
Length: 4.3 mi • Est. 2 h 48 m
#6 - Maple Hill via Long Trail
Glastenbury Wilderness
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(58)
Length: 4.9 mi • Est. 2 h 54 m
#7 - Glastenbury Mountain via Long Trail (Appalachian Trail)
Woodford State Park
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(26)
Length: 22.4 mi • Est. Multi-day
This is a beautiful but challenging two night backpacking trip that gets you back to your car before noon on the third day. All you have to do is park one car at the Stratton Mountain trailhead and another at the LT/AT Trailhead on Route 9. Towards the end of day two, you'll pass the trailhead on Route 9 where you car is parked and will have to backtrack around 4.5 miles the next morning. I recommend this to hike to anyone who wants a taste of a few days on the AT/LT in southern Vermont.Show more
#8 - Long Trail and Bald Mountain Loop
Glastenbury Wilderness
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(14)
Length: 22.6 mi • Est. Multi-day
There are two ways to do this loop: one is to begin at Bald Mountain’s trailhead in Bennington and following the West Ridge Trail to Glastenbury. Or to begin at the Bald Mountain Trail in Woodford. Beginning in Bennington had access to Bald Mountain’s outlook. When you begin from the Woodford side, there is not an outlook point until you reach the summit. The summit of Bald Mountain is the intersection of these two trails with the West Ridge Trail, but the views are hard to see over the treetops. The West Ridge Trail has thick overgrowth compared to the LT, but it’s still accessible. Show more
#9 - Bald Mountain Trail
Bennington, Vermont
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Length: 11.2 mi • Est. 6 h 53 m
A portion of the West Ridge trail to the summit of Glastenbury. A great in/out hike if you want to show a friend/family the benefits of hiking in Vermont. Great views, wildlife and camping opportunities. The south end of the summit is also known as Bear Hollow and is covered in wild blueberries in late summer.Show more
#10 - Waters Hill Cemetery
Green Mountain National Forest
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(36)
Length: 1.9 mi • Est. 45 m
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