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Middleborough, Massachusetts

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

Top Hiking Spots in and near Middleborough

  • 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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  • Dartmouth, Massachusetts

    Hike Frank Knowles–Little River Reserve Trail

    4.6
    4 mi / 295 ft gain
    Frank Knowles-Little River Reserve contains nearly 9 miles of hiking trails to explore. Start off by parking in the white sea shell parking lot. From there you will find the trail marked by a DNRT sign . My group and I walked along the red/boardwalk trail which features a number of boardwalks lea...
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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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  • Quincy, Massachusetts

    Hike The Skyline Trail at Blue Hills

    4.0
    12.7 mi / 2542 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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  • Westport, Massachusetts

    Hike Gooseberry Island

    1.5 mi / 36 ft gain
    Begin an hour before sunset at the intersection between West Beach and East Beach Road. The intersecting roads will lead you to a paved causeway over the ocean. Waves typically clash on either side of you as you drive over the ocean. There is a free parking lot once you reach the opening. To reac...
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  • Providence, Rhode Island

    Neutaconkanut Loop

    5.0
    1.49 mi / 171 ft gain
    To enter the park, you first have to go through a field and past a baseball park. Next, you will see a high slope, you can either enter the trails through here or the stairs at the side. Some of the trails are overgrown and may have ticks or poison ivy so be careful. This place is good for kids a...
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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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  • 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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  • Middletown, Rhode Island

    Birdwatch at Sachuest Point

    1.5 mi
    A trip to Aquidneck Island would not be complete without a quick walk around Sachuest Point. I highly recommend this hike at sunrise, but any time of the day (or year) is great! This nature preserve is home to a large population of tourist-friendly deer, and is visited every winter by at least tw...
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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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  • 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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  • Newport, Rhode Island

    Take a Stroll on the Newport Cliff Walk

    4.6
    3.5 mi
    The 3.5 mile Cliff Walk is a National Recreation Trail in a National Historic District. I chose to start at the western end of Easton's or First Beach at Memorial Blvd. and walk south. The first two-thirds of the walk is very easy walking conditions. Parts of the southern half of the walk are...
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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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  • 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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