Stockbridge, Massachusetts

Top Spots in and near Stockbridge

  • Elka Park, New York

    Devil's Path in the Catskills

    4.0
    22.04 mi / 7733 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 l...
    Read more
  • 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.
    Read more
  • Litchfield, Connecticut

    Photograph Daffodils at Laurel Ridge

    Laurel Ridge is a private owned Farm , the owners are generous enough to let people visit these flowers so please be respectful of there rules.  You may see the Daffodils from Sunrise-Sunset and usually fully bloomed Early April-May. Laurel Ridge is the perfect way to start Spring, the smell and ...
    Read more
  • New Scotland, New York

    Indian Ladder Trail

    4.5
    1.62 mi / 230 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...
    Read more
  • Woodstock, New York

    Overlook Mountain Trail

    4.53 mi / 1348 ft gain
    It is important to know that parking for the head of this trail is great, located on Meads Mountain Rd in Woodstock NY. The trail is clearly a gravel road marked by Red trail markers, on a gradual inline up to the Hotel first, at the 2 mile mark, and then the Fire Tower is 0.5 miles further down...
    Read more
  • 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 ...
    Read more
  • Wilmington, Vermont

    Ward’s Cove at Harriman Reservoir

    Harriman Reservoir — also known as Whitingham Lake — is one of Vermont's largest bodies of water, stretching over 2,000 acres through the hills of Wilmington and Whitingham in the southern Green Mountains. Ward's Cove is one of the reservoir's quieter access points, offering a sheltered launch ...
    Read more
  • Woodford, Vermont

    Woodford State Park Loop

    5.0
    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...
    Read more
  • Woodford, Vermont

    Woodford Trail

    2.41 mi / 203 ft gain
    The Woodford Trail is the lakeside loop hike at Woodford State Park in southern Vermont — circling Adams Reservoir through a unique high-elevation boreal spruce and balsam forest typically found much farther north. At 2.41 miles with just 200 feet of elevation gain, it's an easy, family-friendly ...
    Read more
  • Bennington, Vermont

    The Mile-Around Woods

    5.0
    1.33 mi / 243 ft gain
    The Mile-Around Woods in Bennington, Vermont, offers a moderate hiking trail that spans approximately 1.33 miles. The trail is circular, providing a continuous path through the woods. The terrain is varied, with some flat sections and others that are slightly hilly, making it suitable for interme...
    Read more
  • Windham, New York

    Escarpment Trail

    21.97 mi / 5282 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...
    Read more
  • Niskayuna, New York

    Lisha Kill Preserve Loop

    4.5
    2.22 mi / 200 ft gain
    This 2.2 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...
    Read more
  • 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...
    Read more
  • Wilmington, Vermont

    Mount Olga Fire Tower Loop

    2.25 mi / 667.32 ft gain
    Tucked along Route 9 in Wilmington, Vermont, Molly Stark State Park is home to one of the most satisfying short hikes in the southern Green Mountains: the climb to the Mount Olga fire tower. At just 1.8 miles as a loop, it punches well above its weight — rewarding hikers with a genuine fire tow...
    Read more
  • 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.
    Read more
  • Altamont, New York

    Wolf Creek Falls Preserve White Trail Loop

    3.0
    1.93 mi / 256 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; ...
    Read more