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Stockbridge, Massachusetts

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

Top Hiking Spots in and near Stockbridge

  • Voorheesville, New York

    Hike the Keleher Preserve Loop

    2.0
    3 mi / 1636 ft gain
    The historic preserve is operated by the Mohawk Hudson Land Conservancy, so trails are clearly marked and extremely well maintained. There are features of the original farm that the land was used for from the 18th Century, including hand-thrown stone walls and an old logging road that cuts throug...
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  • Washington, Connecticut

    Hike the Mount Tom Tower Trail

    1.3 mi / 337 ft gain
    Starting from the parking lot of Mt. Tom State Park, hop onto the Tower Trail (yellow trail) which leads more into the woods. During winter time, the trail may be slippery, please use your best judgement and always know your limits. Gaining about 300 feet in total elevation in approximately 1 mil...
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  • Simsbury, Connecticut

    Hike to the Heublein Tower on Talcott Mountain

    4.3
    2.54 mi / 404 ft gain
    The Heublien Tower Trail, located just inside the Talcott Mountain State Park entrance off of Route 185 in Simsbury CT, is a short 1.25 miles. While the hike isn't long, the first 1/3 of a mile is a steep incline that will get your heart pumping. The trail itself it very well kept, and although ...
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  • Elka Park, New York

    Hike Twin Mountain

    6 mi / 1586 ft gain
    The DEC Parking lot, is located at the very end of a dead end, along Prediger Rd. Start at the trail head to the right of the trail kiosk and sign in sheet. The trail starts out very easy going as you approach the base of Twin. At mile 0.25, you’ll hit a junction where you’ll turn RIGHT towards T...
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  • Elka Park, New York

    Hike Indian Head Summit via Jimmy Dolan Notch Overlook

    4.9 mi / 1512 ft gain
    The view from the summit of this hike is incredible. Bring a sack lunch and a camera - you'll want to stay for a while! This trail is open for use year-round and provides great snowshoeing in the winter and fabulous wildflowers in the spring and summer. This is also a great location for birding!
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  • Elka Park, New York

    Backpack the Eastern Half of Devil's Path in the Catskill Mountains

    5.0
    14 mi / 3900 ft gain
    The Eastern half of Devil's Path has four major summits: Indian Head, Twin, Sugarloaf and Plateau. Each summit is a straight climb up and down, then back up to as much as 3,900 ft. There are some sparse sections of level ground, but most is a steep descent uphill or steep slide downhill. Your ...
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  • Elka Park, New York

    Backpack Devil's Path in the Catskills

    24.2 mi / 9000 ft gain
    Devil's Path is roughly more than 24 miles long, althought it feels like an eternity of milage. Going thru the summits of Indian head, Twin, Sugarloaf, Plateau, Hunter, and Westkill Mountains.Its brutal. Its painful, Its unique. Be prepared for anything and everything. You will encounter wild lif...
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  • Washington, Connecticut

    Hike Meeker Trail

    3.3 mi / 639 ft gain
    Meeker Trail is a 3.3 mile out and back hike that takes you by a lake located near New Preston, Connecticut.
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  • Voorheesville, New York

    Hike the Indian Ladder Trail

    4.5
    3.5 mi / 200 ft gain
    There are many parking areas within the park. Park at the overlook parking. From here you head west following the wood fence. This is the Cliff Top trail. Approximately after walking 0.5 miles you will reach the stairs that will lead you to the base of the cliffs. This marks the start of the...
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  • Elka Park, New York

    Camp at Sugarloaf Mountain in the Catskills

    4.0
    6 mi / 1500 ft gain
    Begin by parking at the end of Mink Road in Elka Park (GPS:N42 08.593, W74 09.479). It will be a .7 mile hike to camp. Follow the rocky woods road to the junction where there is a SPRING sign. Continuing straight will take you to the water source. If you do not need water, turn left when you see ...
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  • Woodford, Vermont

    Woodford State Park Loop

    2.41 mi / 203 ft gain
    A great loop for the summer, Woodford is also amazing when winter winter comes to the State Park. It also comes earlier than just about anywhere else in Southern Vermont. At 2,400 feet above sea level, this is an easy spot to find winter without spending a fortune at the local ski resorts. Woodfo...
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  • Windham, New York

    Backpack the Catskill's Escarpment Trail

    32.4 mi / 8000 ft gain
    The Escarpment Trail runs the length of the Catskill Escarpment. The Escarpment rises steeply from the valley below forming the northeast corner of the Catskill Mountains. It offers great views toward the Adirondack Mountains to the north and the great Hudson River to the east. The trail is moder...
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  • Schenectady, New York

    Hike the Lisha Kill Preserve Loop

    5.0
    2.3 mi / 324 ft gain
    This 2.3 mile loop trail is lightly trafficked and great for all skill levels. Starting out the trail register, you will see signs from The Nature Conservancy which manages the preserve. Descending down a hill with lots of exposed tree roots, you will then cross over the meandering Lisha Kill and...
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  • Woodstock, New York

    Sugarloaf Mountain via Blue Trail

    6.54 mi / 2297 ft gain
    Sugarloaf Mountain, is one the 35 highest peaks in New York's Catskills at 3806 ft. There are many ways to approach this peak, and this is an out-and-back hike via Mink Hollow. The parking area is located at the end of Milk Hollow Rd (42.10405386879072, -74.17148500019927). From here, get on the...
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  • Hampden, Massachusetts

    Goat Rock Trail

    2.67 mi / 659 ft gain
    Goat Rock Trail is an out-and-back trail where you may see beautiful wildflowers located near Hampden, Massachusetts.
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  • Altamont, New York

    Hike through the Wolf Creek Falls Preserve

    3.0
    3 mi / 200 ft gain
    Over 3 miles of trails provide access to all parts of the preserve, and end up winding through mixed terrain including a wetland, waterfalls, and old stone walls. The property crosses the Bozenkill Road at two points on either side of private parcels (with beautiful homes), so be vigilant there; ...
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