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Chatham, Massachusetts

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

Top Hiking Spots in and near Chatham

  • Harwich, Massachusetts

    West Reservoir

    5.0
    2.65 mi / 59 ft gain
    West Reservoir is a loop trail that takes you by a lake located near Harwich, 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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  • Provincetown, Massachusetts

    Hike Provincetown Dunes on the Cape Cod National Seashore

    4.8
    2.8 mi / 287 ft gain
    Begin your journey from a small parking area that holds 3 cars just off route 6 (additionally you can park on the side of the road) The trail head is unmarked until about 50' into the woods where you will find a sign describing the rich history of the area. Continue up the large sand dune immedia...
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  • Provincetown, Massachusetts

    Explore Hatches Harbor and Race Point

    5.0
    3.3 mi
    Hatches Harbor & Race Point Lighthouse trail is not super long or difficult.  Pretty straight forward, at least up to Hatches Harbor. There is a small parking lot that fits about six cars off Province Lands Rd.  I think we had a good amount of rain leading up to that day and the trail reflect...
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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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  • 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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