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Plymouth, Massachusetts

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

Top Running Spots in and near Plymouth

  • Hanson, Massachusetts

    Burrage Pond Indian Trail

    5.0
    3.39 mi / 194 ft gain
    Burrage Pond Indian Trail is an out-and-back trail where you may see beautiful wildflowers located near Hanson, Massachusetts.
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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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  • 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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  • Truro, Massachusetts

    Hike the Pamet Area Trail

    1.9 mi
    Pamet Area Trail is in Truro, towards the ocean within the Cape Cod National Seashore.  As we were driving to the parking area it felt like it was wrong, as it often does.  There was a dead end and school signs, which are for the N.E.E.D. Academy (apparently also doubles as a hostel during the su...
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  • Boston, Massachusetts

    Run the Arnold Arboretum Trail

    5.0
    2.6 mi / 150 ft gain
    Park in the lot off of Arborway to access the trail. This place is gorgeous year round. The winter offers a quiet solitude, fall boasts bright colors, spring is the most beautiful as the flowers start to burst and cherry blossoms take over, and summer is overwhelmingly green. There are dozens of ...
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  • Boston, Massachusetts

    Run the Jamaica Pond and Victorian Jamaica Plain Loop

    5.0
    1.5 mi / 95 ft gain
    Park in the Jamaica Pond parking area. You can go either direction on this loop trail, which is highly trafficked and dog-friendly. Keep a lookout for (and a respectful distance from) the wildlife that live here. The loop around Jamaica Pond itself is 1.5 miles. The best part about running in thi...
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  • Cambridge, Massachusetts

    Bike or Run on the Charles River Path

    5.0
    10 mi
    The Charles River Path becomes a center of activity in Boston, especially during the summer, and you can run (or bike) it! It is a paved pathway that travels along both sides of the Charles River from the North End of the city to Allston and beyond. There are several bridges along the way with pe...
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  • Wellesley, Massachusetts

    Walk along Lake Waban

    3 mi
    Note: The campus is currently closed due to COVID-19 restrictions. This is a lake on Wellesley College Campus.  It is easy to get to from just about any direction. Just park and walk toward the lake, and there are paths that will take you there. The easiest place to park (pinned on the map) is ju...
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  • Chilmark, Massachusetts

    Menemsha Hills Reservation Loop

    5.0
    2.98 mi / 344 ft gain
    GPS service in densely wooded areas on the Vineyard is hard to come by, so plugging in Menemsha Hills Reservation before getting on the road is advised. Traveling down N Road, you'll find an unmarked gravel road located between Turtle Cove and Trustees Lane. A short 400 meter drive will take you ...
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  • Edgartown, Massachusetts

    Hike Huckleberry Barrens Trail

    0.5 mi
    The Huckleberry Barrens property is a 17 acre expanse of land in Katama, MA managed by the Sheriff's Meadow Foundation. Though the property is quite vast, the trail loop is only approximately 0.5 miles. Quite conveniently, If you're looking to extend your walk, run or bike, there is an opening ha...
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