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Chester, Connecticut

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

Top Chillin Spots in and near Chester

  • 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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  • 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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  • Charlestown, Rhode Island

    Watch the Sunrise at East Beach, RI

    Walking over the dunes in the dark you can hear the waves breaking on shore from the parking lot. Wet suited up, camera in hand, make your way over the dunes and down to the water. East Beach is a sandy beach and with the right swell size and direction you'll get some sizable shore break to play ...
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  • Washington, Connecticut

    Hike the Mount Tom Tower Trail

    1.3 mi / 337 ft gain
    Starting from the parking lot of Mt. Tom State Park, hop onto the Tower Trail (yellow trail) which leads more into the woods. During winter time, the trail may be slippery, please use your best judgement and always know your limits. Gaining about 300 feet in total elevation in approximately 1 mil...
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  • Charlestown, Rhode Island

    Visit the Frosty Drew Observatory

    The Frosty Drew Observatory is located near the tip of southern Rhode Island, which means apart from summer this is a very quiet beach town. The isolation from major urban areas provides the perfect conditions for star-gazing. The building itself is located on a large plot of land dedicated to na...
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  • Charlestown, Rhode Island

    Car Camp at Charlestown Breachway Campground

    Rhode Island is nicknamed the Ocean State for a reason, and camping by the coast is something absolutely necessary while in New England. During the summer and early fall, Charlestown, RI, as well as the surrounding beach towns, come alive with tourists from all over the globe. The Breachway Campg...
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