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Windham, Connecticut

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

Top Chillin Spots in and near Windham

  • Granby, Connecticut

    Hiking Enders Falls

    4.0
    Enders State Forest sprawls over approximately 2000 acres, and is found within the towns of Granby and Barkhamsted in Connecticut.  Enders has a good sized parking lot directly on Route 219.  From the junction of Route 219 and Route 20, visitors will proceed west on Route 219 for 1.2 miles and tu...
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  • Jamestown, Rhode Island

    Explore Beavertail State Park

    5.0
    Rhode Island isn't exactly on everyone's map, I've even met strangers in other parts of the U.S. who have no idea where the tiniest state in the country is. It's usually lumped in with Connecticut and Massachusetts, but for us locals from little Rhody, Rhode Island is it's own world of adventure ...
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  • Cheshire, Connecticut

    Hike to Roaring Brook Falls

    1.2 mi / 377 ft gain
    Arriving to the falls, parking is residential but don't worry everyone is friendly. Starting off the hike you will walk past a cool pond where you may be able to see some wildlife. Continuing on, you will follow the marked trail where it will take you further into the woods while gaining elevatio...
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  • New Shoreham, Rhode Island

    Walk to North Lighthouse

    1 mi / 0 ft gain
    In order to reach the Lighthouse you must walk along the trail that begins at the end of Corn Neck Rd. This walk is along the beach and then veers off to the left once you get closer to the light house (the seventh picture shows the start of the walk). It's only a half mile to the light house, bu...
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  • Shelter Island, New York

    Hike through the Mashomack Nature Preserve

    10 mi
    Just a short ferry ride from the Hamptons, South Ferry Road is exactly where it sounds; very close to the South Ferry of Shelter Island. The parking lot of Mashomack Preserve is marked by a large sign. When you walk in, you'll see a large nature center. Sign in at a clipboard at the table out fro...
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  • Newport, Rhode Island

    Drive the Ocean Drive Historic District

    5.0
    10 mi
    This drive encompasses all that is Newport, RI.  Known for its rocky shores and numerous sea-side mansions, this drive allows you to both view it all from the safety of your car, and has several spots to pull off to get out and get a better view.  There are grassy park areas as well that are perf...
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  • Montauk, New York

    Stroll along the Montauk Point Lighthouse Cliff Walk

    4.5
    1 mi
    The Montauk Point Lighthouse is one of the main attractions of "The End" of Long Island, but I've only ever walked around it on the cliff walk.When you get to the lighthouse, you can park in the parking lot (depending on when you go there may be a $8 fee). Right along the edge overlooking the wa...
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  • Montauk, New York

    Climb the Bluffs of Shadmoor State Park

    1.2 mi / 100 ft gain
    I've never actually been into the Shadmoor State Park, but you can climb up and onto the bluffs from the beach easily; well kind of easily.Most of the parking lots along the beach require Hamptons residency tags, so you can't park right next to beach entrances... bummer. We typically park along ...
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  • New Shoreham, Rhode Island

    Explore Block Island

    5.0
    Block Island, a small island off the coast of the Rhode Island mainland, is well-known as a local summer playland. Tourists typically go to the quaint New England island in the summer months for the biking, hiking, sailing, kayaking, fishing and 17 miles of beaches.Although you can bring a car o...
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  • New Shoreham, Rhode Island

    Explore Block Island on Mopeds

    Block Island offers beautiful beaches, lighthouses, cliffs, and harbors - but what's the best way to see them all? Mopeds of course! We went through Island Moped & Bike but there are other options if you want to shop around. We chose them because they had a special rate for an afternoon/eveni...
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  • New Shoreham, Rhode Island

    Explore the Mohegan Bluffs

    If you make the ferry ride to Block Island the bluffs are a must-see. From the town where the ferry ports, it's about two miles to get there. If you don't travel with your car you can always walk there via the road, bike ride, or rent a moped! There is no fee to use the beach and it can be access...
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  • New Shoreham, Rhode Island

    Explore the South East Lighthouse

    If you're visiting the Mohegan Bluffs, you should take the extra time to see the Lighthouse next to them. There's a beautiful overlook looking out onto the Atlantic and a bench to relax in the grassy hill. It's free to walk around the grounds and it's only about 2 miles from the town the ferry po...
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