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Great Barrington, Massachusetts

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

Top Chillin Spots in and near Great Barrington

  • 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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  • Cohoes, New York

    Capture a Sunset at the Colonie Town Park

    5.0
    Not all adventures have to involve scaling crazy-steep mountains or paddling down intense white-water rapids. Some of the best adventures are the relaxing and mellow ones right in our backyards. When I cannot get into the woods every day, I go to the Colonie Town Park, just 10 minutes from my hou...
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  • Southington, Connecticut

    Hike the Crescent Lake & Metacomet Trail Loop

    4.0
    2.4 mi / 269 ft gain
    The hike to view Crescent Lake is peaceful. You can either walk through the woods where you will be blessed with natures finest birds and wildlife or you can take the trail along the lake edge. Both are similar distances and lead to the same hill at the end! Once you get to the top take a left on...
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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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  • Manchester, Connecticut

    Explore Wickham Park

    5.0
    Wickham Park Is open the first weekend in April and closes the last weekend in October. Entrances fees are $5 Monday-Friday and $7 Saturday-Sunday. The park is known for its 250 acres of  open fields, wildflowers, gardens, ponds and nature center. There is no where else can you go have a picnic w...
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