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Chestertown, New York

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

Top Chillin Spots in and near Chestertown

  • Poultney, Vermont

    Camp on Mount St. Catherine

    5.0
    Looking for the best view in all of Poultney, Vermont? Look no further than Lake St. Catherine Mountain. Located within Deane's Nature Preserve, this fast and easy hike tops as one of the best views and camping spots for the little time and energy needed to reach the summit. Only 30-45 minutes fr...
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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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  • New Russia, New York

    Explore Split Rock Falls

    5.0
    The the easiest and the fastest access of any New York waterfalls Split Rock Falls, is within 10 feet of the parking lot and as soon as you open the car door you hear the water gushing down the Boquet River. The clear, cold waters of Split Rock Falls cascade through groves of hemlock and spruce, ...
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  • Keene Valley, New York

    Hike Rooster Comb Mountain

    5.2 mi / 1795 ft gain
    Take in two unique views of the Adirondacks on one hike. Rooster Comb offers a great 5.2 mile round trip hike that gives you some unique vantage points. Starting from the parking lot you cross over a nice wooden bridge to the trail registry. Remember to sign in. Next you'll come up on a pond in w...
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  • Long Lake, New York

    Camp along Section 2 of the Northern Forest Canoe Trail

    The Northern Forest Canoe Trail is a 740-mile paddling trail with the western terminus located in Old Forge, New York and the eastern terminus in Fort Kent, Main.  Section Two is a 42.4 mile journey in the Adirondacks of New York from Long Lake to Saranac Lake.  There are primitive campsites and ...
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  • Lake Placid, New York

    Hike Phelps and Tabletop Peaks

    12.6 mi / 3300 ft gain
    The Adirondack Loj is a BEAUTIFUL place to go to, even if you do not plan on hiking. Located just ten minutes outside of the famous Lake Placid, you do not want to miss visiting this alluring Loj in the woods.Starting from Lot number 1 from the Adk Loj, begin hiking the 2.1 miles to Marcy Dam. Th...
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  • Keene, New York

    Explore the Cascade Lakes, NY

    4.0
    Just off Route 73, in between Lake Placid and Keene, in the gorgeous Adirondack Mountains sits two of the most beautiful lakes and get this...you can park RIGHT on the bank, open the hatch and chill. Don't pass this one up.There is a little gravel road right off the highway that leads to the midd...
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  • Dorset, Vermont

    Hike 'The Merck'

    4.0
    2.5 mi
    Of the 10 trails at The Merck, The Wildlife Trail is a great hike through the forest that offers you the best way to see wildlife, streams and tracks. You can do the whole hike as a loop in about 2-2 1/2 hours or shorten it up with some shortcuts if you just want a quick hike. Great for family ...
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  • Gloversville, New York

    Drive the Adirondack Trail Scenic Byway

    3.0
    This scenic byway starts in Fonda, NY and travels along Route 30 to Malone, NY.  The area described and pictured here is a 65 mile stretch from Mayfield to Indian Lake. Starting in Mayfield you will head north driving past the Great Sacandaga Lake. Continuing through the town of Hope  you will dr...
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  • Lake Placid, New York

    Ice Skate Mirror Lake

    Looking for ice skating a bit more off the beaten path? Try Mirror Lake! Open 24/7! The best place to start is at the south end of the lake where you can also find a nearby shop to rent skates if you don't have them. If you do not feel like going on the 2 mile loop around the lake, you can stick ...
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  • Lake Placid, New York

    Hike Up Cobble Hill

    5.0
    Looking for a great family hike up in the Adirondacks? Take a look into Cobble Hill right off of Mirror Lake in Lake Placid. This is a perfect hike for those with younger kids and want to expose them to hiking.Cobble Hill has a little bit of everything all packed into the short distance. The tr...
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  • Lake Clear, New York

    Relax at Ampersand Beach

    1.1 mi / 20 ft gain
    Located across from the Ampersand Mountain trailhead on NY Route 3, a trail will take you a short walk (about a half mile) to this beautiful, quiet beach on the shores of Middle Saranac Lake. Starting at the trailhead, you will continue along an unmarked but clear footpath that trails through the...
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