Middletown, Rhode Island

Looking for the best hiking 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 Hiking Spots in and near Middletown

  • 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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  • Randolph, Massachusetts

    Hike the Ponkapoag Pond Trail

    4.0
    3.82 mi / 173 ft gain
    Park at the end of Ponkapoag Trail Road to access the trail. Dog friendly, open year round. 
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  • Milton, Massachusetts

    Houghton's Pond Recreation Area

    1.2 mi / 79 ft gain
    Houghton's Pond Recreation Area is a loop trail that takes you by the lake located near Milton, Massachusetts.
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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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  • Mansfield, Connecticut

    Hike Nipmuck Trail

    5.0
    8.3 mi / 748 ft gain
    Nipmuck Trail is a 8.3 mile out and back hike that takes you past wildlife located near Mansfield Center, Connecticut.
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  • Ashland, Massachusetts

    Hike the Ashland Reservoir Trail

    5.0
    3.2 mi / 68 ft gain
    Park in the lot on State Park Road (see map) to access the trail. It's a popular trail that is dog-friendly. Pay attention to the trail as at parts it is not well marked. 
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  • Quincy, Massachusetts

    Skyline Trail Loop at Blue Hills

    4.0
    9.63 mi / 1358 ft gain
    Park in the lot across from Batterymarch Rd off of Willard St. Access the Skyline trail from here, it is marked blue. Follow the signs. The trails in Blue Hills are perfect for training for backpacking because they are so steep and rocky. I would fill up a big pack and take the skyline trail up t...
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  • Norwell, Massachusetts

    Hike the Norris Reservation Loop

    2.4 mi / 60 ft gain
    Choose from multiple trails in Norris that offer beautiful views of the the North river and marshland. Great spot to do some trail running through the woods and see the river too. There is also a pond a short distance from the parking lot that offers a great fishing spot with a picnic table nearb...
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