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Best trails in Brattleboro

224 Reviews
Looking for a great trail near Brattleboro, Vermont? AllTrails has 7 great hiking trails, dogs leash 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 Monadnock State Park or Pillsbury State Park, we've got you covered. You'll also find some great local park options, like Ball Mountain State Recreation Area or Madame Sherri Forest. Just looking to take a quick stroll? We've got 4 easy trails in Brattleboro ranging from 0.7 to 2 miles and from 515 to 2,414 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 Brattleboro
Top trails (7)
#1 - Black Mountain Trail
Black Mountain Natural Area
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(43)
Length: 3 mi • Est. 1 h 51 m
Black Mountain rises abruptly from the West River in Dummerston to a horseshoe ridge with a summit of 1,280 feet. The mountain originated as a mass of molten rock deep beneath the surface of the earth between 345 and 395 million years ago. Erosion has exposed the granite that forms the core of the mountain. The lower slopes of Black Mountain are covered by hemlock and hardwoods such as sugar maple and beech. The pluton’s steep upper slopes and summit include craggy granite bedrock ledges covered by a thin layer of poor acidic soil. Here where nutrient-needy and water-loving plants can’t grow, the only pitch pine-scrub oak woodland in Vermont flourishes. Smallish pitch pines, red and white pines, oaks and red maples, lift gnarled limbs above a grassy glade cloaked in lowbush blueberry and huckleberry. Lichen-covered glacial erratics – boulders dropped by melting glaciers – are scattered about. From the top of Black Mountain there are views as far as New Hampshire’s Mount Monadnock, and into the West River and Connecticut River valleys.Show more
#2 - Mount Olga via Tower Trail
Molly Stark State Park
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Length: 1.6 mi • Est. 51 m
#3 - Sunset Trail
Fort Dummer State Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(41)
Length: 1.1 mi • Est. 32 m
#4 - Mount Olga and Tower Trail Loop
Molly Stark State Park
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Length: 2 mi • Est. 1 h 9 m
#5 - Upper Trail and Beaver Pond Trail Loop
Hillwinds Trails
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Length: 1.9 mi • Est. 53 m
#6 - Cross Mountain Bishop Trail
Brattleboro, Vermont
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(1)
Length: 0.7 mi • Est. 18 m
#7 - Black Mountain Trail [CLOSED]
Brattleboro, Vermont
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Length: 2.5 mi • Est. 1 h 40 m
The Nature Conservancy has closed the Black Mountain Trails due to COVID 19. The complex of dry ridge-top communities on Black Mountains rugged granite contours is exemplary for the region. Show more