Stratton, Vermont

Looking for the best hiking in Stratton? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Stratton. The detailed guides, photos, and reviews are all submitted by the Outbound community.

Top Hiking Spots in and near Stratton

  • Erving, Massachusetts

    Rattlesnake Loop to Red Trail

    1.97 mi / 676 ft gain
    Rattlesnake Loop to Red Trail is a loop trail that provides a good opportunity to view wildlife located near Erving, Massachusetts.
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  • Mendon, Vermont

    Hike to Killington Peak

    5.0
    3.4 mi
    The trail head (Bucklin Trail) is found a couple of miles up Wheelerville Road on the left. Wheerlerville is a dirt road that will be muddy in the spring and summer. The drive is long enough that you will think you did something wrong, but you haven't! the trail head will eventually pop up.The tr...
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  • Jaffrey, New Hampshire

    Summit Mt. Monadnock via Marlboro Trail

    5.0
    4 mi / 2300 ft gain
    Start at the Marlboro Trailhead (you can enter this in Google maps) off Shaker Road. There's parking and porta-potty bathrooms. The trail is well-marked with white dashes/M marks all the way up. Once on trail, the initial 800 ft climb is through forested terrain with a few brooks and streams alon...
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  • Jaffrey, New Hampshire

    Hike MT Monadnock via White Arrow Trail

    4.3 mi / 1485 ft gain
    Arriving at the Old Toll Road/Halfway House Trail head you will have $5 entrance fee. Starting on the Old Toll road you'll find yourself walking on a gradual incline into the beautiful New Hampshire wilderness. Everything you see and smell is fresh and vibrant. Following the road for 1.1 miles yo...
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  • Deerfield, Massachusetts

    South Sugarloaf Trail

    1.48 mi / 404 ft gain
    South Sugarloaf Trail is a loop trail that takes you by a river located near South Deerfield, Massachusetts.
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  • Jaffrey, New Hampshire

    Mount Monadnock via White Dot Trail

    4.5
    3.46 mi / 1699 ft gain
    Monadnock State Park is located in and around the 3,165-ft. Mount Monadnock. Mount Monadnock is crisscrossed by many miles of well-maintained hiking trails. The popular White Dot Trail (2.2 miles) is the shortest but steepest ascent to the summit, accessible from the Monadnock State Park headquar...
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  • Jaffrey, New Hampshire

    Mount Monadnock via White Dot & White Cross Loop

    4.5
    3.7 mi / 1686 ft gain
    The White Dot Trail is the shortest, steepest ascent to the summit, while White Cross has a slightly easier grade down with very little difference in distance.  Therefore, per the park's rangers, the best way to conquer this loop is White Dot up, White Cross down.The White Dot Trail begins at Mon...
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  • Appalachian Trail, Vermont

    Thundering Brook Falls

    4.7
    0.44 mi / 112 ft gain
    The hike to Thundering Brook Falls is kid friendly and fun for the whole family. At only .4 miles roundtrip, this is an excellent quick workout. Dogs are allowed on this trail but must be kept on leash. This trail is hiked year-round but is best used in the spring, summer, or during fall colors. 
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  • Woodstock, Vermont

    The Pogue and Mount Tom Trail

    4.38 mi / 751 ft gain
    The Pogue and Mount Tom Trail is a loop trail that takes you by a lake located near Woodstock, Vermont.
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  • Castleton, Vermont

    Hike around Taconic Mountains Ramble State Park

    Taconic Mountains Ramble State Park is a unique collection of hiking trails and walking paths that meander more than 204 acres of fields, forests, gorges, cliffs, and gardens. The best way to explore these enchanting trails is to pack a picnic and lace up your hiking boots for a full-day ramble. ...
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  • Fort Ann, New York

    Buck Mountain via Shelving Rock Road

    4.44 mi / 1145 ft gain
    There are a few options for this mountain. The route described is the easiest approach and therefore the nicest for a sunset hike. Starting at the trailhead on Shelving Rock Road the sign will read 2.5 miles to the summit. The trail is easy to follow and marked with blue discs. Gentle grade for ...
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  • Fort Ann, New York

    Sleeping Beauty and Bumps & Fishbrook Ponds

    6.16 mi / 1138 ft gain
    Parking is available at the end of Dacy Clearing Rd. There are great primitive campsites throughout the area. In winter and mud season you will have to park at the start of Dacy Clearing Rd which adds 1.6 miles each way. From the parking clearing, turn right passing through a gate. Soon you r...
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  • Newbury, New Hampshire

    Hike to Lake Solitude, NH

    4.0
    4.8 mi / 2510 ft gain
    The two most popular routes to Lake Solitude are the Newbury Trail and Andrew Brook Trail.  The round-trip distance of the hikes are 4.8 miles and 3.8 miles. Both could be described as moderate in terms of difficulty. The Newbury trail is accessed from Lakeview Ave and Andrew Brook Trail can be a...
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  • East Nassau, New York

    Kinderhook Creek

    5.0
    1.62 mi / 308 ft gain
    Kinderhook Creek is a loop trail that takes you by a river located near Stephentown, New York.
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  • Hartford, Vermont

    Camp at Quechee State Park

    4.0
    Located on the Ottauquechee River, Quechee State Park offers camping options right beside one of Vermont's most famous gorges—Quechee Gorge. The steel bridge that passes over the 165 ft. gorge is just one of many spectacular views in this area. Quechee State Park is on Route 4 and easily accessi...
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  • Clemons, New York

    Black Mountain Loop

    6.79 mi / 1319 ft gain
    Black Mountain is located on the Eastern side of Lake George and is the tallest mountain above Lake George. The trailhead is located on Pike Brook Road (off from Hulett's Rd, Route 6) in Clemons, NY. The parking area is about one mile up Pike Brook Road, on the right. This hike to Black Mountain...
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