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Gloucester, Massachusetts

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

Top Chillin Spots in and near Gloucester

  • Ipswich, Massachusetts

    Photograph Castle Hill

    4.0
    Castle Hill refers to either a 165-acre drumlin surrounded by sea and salt marsh or to the mansion that sits on the hill. Both are part of the 2,100-acre Crane Estate located on Argilla Road in Ipswich, Massachusetts.Take a walk through the public garden or down to the beach. Plenty of beautiful ...
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  • Hull, Massachusetts

    Explore the Bunkers at Fort Revere

    Fort Revere is an 8-acre (3.2 ha) historic site situated on a small peninsula located in Hull, Massachusetts. It is situated on Telegraph Hill in Hull Village and contains the remains of two seacoast fortifications, one from the American Revolution and one that served 1898-1947. There are also a ...
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  • Boston, Massachusetts

    Freedom Trail

    4.7
    2.9 mi / 121 ft gain
    Park along the trail and then hop on. The Freedom Trail allows you to not only see the most beautiful parts of Boston (which is an absolutely gorgeous city) but you can learn some history too! Head off the trail a bit to explore the Charles River, the waterfront near the aquarium and picturesque ...
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  • Portsmouth, New Hampshire

    Relax at Prescott Park

    5.0
    Prescott Park is a waterfront park in Portsmouth, New Hampshire that is famous for its extensive flower gardens.  During the warmer months, visitors can enjoy the blooms of the annual and perennial beds, sit in the shade of the Japanese crabapple trees, and relax on the white benches along the pe...
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  • York, Maine

    Photograph Nubble Lighthouse

    4.8
    Officially named Cape Neddick Light, though more commonly known as Nubble Light, this lighthouse is part of the National Register of Historic Places and is a local favorite for photography. The lighthouse park is located just over the New Hampshire / Maine state line in New England, in York, ME....
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  • Acton, Massachusetts

    Hike the Pratt's Brook Conservation Area Loop

    4.0
    1.5 mi / 85 ft gain
    Park in the small parking area right before the trailhead. *Notice this parking area is small and only fits about 3-4 cars so prepare to find street parking on a busy day. You can punch in the coordinates to a GPS if you need help finding it: 42.4545482, -71.4358192.  The loop is very diverse wit...
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  • Ogunquit, Maine

    Watch the Sunrise from the Marginal Way Trail

    5.0
    2 mi / 70 ft gain
    Park near the Oceanside Oarweed restaurant or any other public spots on the cove's peninsula. Marginal Way is a nicely paved 1.25 mile out and back path, perfect for a morning walk or run on the rocky coast. Catch fishermen, lobstermen, and recreational boats as they leave, or choose to sit at on...
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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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  • Provincetown, Massachusetts

    Dunes' Edge in Provincetown

    Cape Cod, Massachusetts is full of campgrounds and dunes to explore, but the best of the two are located at the very end of the cape, around the areas of Truro and Provincetown. Travel to the very beginning (or end, depending on how you look at it) of historic U.S. Route 6, which spans from Prov...
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  • Groton, Massachusetts

    Catch a Sunset at Gilbert Hill

    5.0
    1 mi
    From Rt. I-495 Exit 31, Gibbert Hill has one of the greatest sunsets around Groton, MA area. You will see a lot of cows and even a castle. This is a very easy hike and a not so easy place to park, you have to leave you car on the side of the road, which is totally fine, I guess, it is easy.The wa...
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