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Dover Plains, New York

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

Top Chillin Spots in and near Dover Plains

  • Greene County, United States

    Hike to Newman's Ledge

    4 mi / 584 ft gain
    Located in the beautiful Catskill Mountains, this is an outdoors-mans(and woman's) dream spot! Although this hike is accessible year round, if you decide to go during the summer you should expect crowds. Luckily, there are so many different trails and activities that it won't even matter. North-S...
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  • Meriden, Connecticut

    Hike the Metacomet, Blue, and Yellow Loop

    5.0
    4.5 mi / 976 ft gain
    Start from the Castle Craig road entrance. Walk until you're greeted by a beautiful reservoir. You'll notice the strange but beautiful Mine Island in the middle of all this. You'll also notice markers for White Trails and Yellow Trails. The White Trail is an easier/wider trail. The Yellow Trail C...
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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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  • 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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  • Meriden, Connecticut

    Higby Mountain Trail

    2.11 mi / 486 ft gain
    The popular route for this hike is to park your car at the base of the trail which is located right before merging onto 91-S in Middlefield, CT. The parking lot does seem to get crowded mid-day, especially if the weather is nice!  The beginning of the hike is mostly flatter land and an incline w...
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  • Bridgeport, Connecticut

    Stroll around Fayerweather Island

    0.5 mi
    Parking is at the end of Barnum Road in the Seaside Park.  Though the lighthouse grounds are accessible the tower itself is not open to the public.  To access the island you must walk across the breakwater.  Please use caution as it is uneven footing and at times can be slippery.  From the isla...
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  • Grahamsville, New York

    Swim at Peekamoose Blue Hole

    3.8
    To get there: From Sundown, NY, head 10 miles on Route 42 until you see a large parking area on the right with a sign for the Peekamoose Mountain area. Follow the signs from the parking area to the creek. Swimming Hole Coordinates: (41.9182, -74.4215) You can cool off from NY's warm weather and d...
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  • Phoenicia, New York

    Camp at Woodland Valley

    3.0
    If you are looking for a great campground up in the Catskill Mountains of New York then you definitely have to check out Woodland Valley Campgrounds. Located about 2 hours north of New York City, it is the perfect place to go to get off the grid. No service for about 30 minutes in any direction.T...
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  • Big Indian, New York

    Camp on Giant Ledge

    4.5
    1.5 mi / 975 ft gain
    Giant Ledge is a great hike in the Catskills if you are looking for something short, with incredible views, and camping options. There are not many hikes with better views then this in the Catskills, so why not spend as much time as possible up there?  There are a few camping spots you can grab w...
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  • Stamford, Connecticut

    Hike Cove Island Park Loop Trail

    5.0
    1.1 mi / 3 ft gain
    This trail is accessible year round and features water views of the Long Island Sound with beach access. The trail is a popular spot for walking, biking, fishing, and even bird watching. But if you’re not quite in the mood to get your steps in, you can use the small beach to sit and chat with a f...
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  • Middletown, Connecticut

    Explore Wadsworth Falls

    5.0
    0.25 mi
    When it comes to exploring Wadsworth Falls its ease of access couldn't be better. As soon as you pull into the parking lot you hear the falls roaring. Take the quick walk to see the picturesque scenery.Facts about Wadsworth Falls:Height: 25ft tall and doubled in width Rock: Hampden Basalt -the ro...
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