Middletown, Rhode Island

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

Top Chillin Spots in and near Middletown

  • Sutton, Massachusetts

    Hike the Purgatory Chasm Trail

    4.6
    1 mi / 115 ft gain
    For this 1-mile hike, you can park at the Purgatory Chasm Visitor Center. From there hit the trail and explore the unusual gap between the tall granite walls, which might be adorned with climbers. Great for all ages and dogs are welcome too. The trail is open March-November.
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  • Chaplin, Connecticut

    Hike to Diana's Pool

    4.0
    1.3 mi / 45 ft gain
    The drive to Diana's Pool is worth it in an of itself, taking you through the backroads of Eastern Connecticut. To begin the hike just simply enter the woodland path and follow the trail. In order to go under the bridge just simply take the first left in the path and there will be a stream that f...
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  • Montauk, New York

    Shadmoor State Preserve Trail

    2.33 mi / 192.26 ft gain
    Shadmoor State Park Loop: Montauk's Bluff Trail with Atlantic Views The Shadmoor State Park Loop delivers a 2.3-mile coastal adventure along dramatic 100-foot bluffs overlooking the Atlantic Ocean, just minutes from Montauk Village. This easy loop trail winds through rolling shadbush-covered ter...
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