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Sturbridge, Massachusetts

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

Top Hiking Spots in and near Sturbridge

  • Deerfield, Massachusetts

    South Sugarloaf Trail

    1.48 mi / 404 ft gain
    South Sugarloaf Trail is a loop trail that takes you by a river located near South Deerfield, Massachusetts.
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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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  • West Greenwich, Rhode Island

    Stepstone Falls via Ben Utter Trail

    5.0
    2.64 mi / 125 ft gain
    Stepstone Falls via Ben Utter Trail is an out-and-back trail that takes you by a waterfall located near West Greenwich, Rhode Island.
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  • Erving, Massachusetts

    Rattlesnake Loop to Red Trail

    1.97 mi / 676 ft gain
    Rattlesnake Loop to Red Trail is a loop trail that provides a good opportunity to view wildlife located near Erving, Massachusetts.
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  • Norwich, Connecticut

    Explore Yantic Falls Historic District

    0.3 mi / 26 ft gain
    The Yantic Falls Historic District encompasses a historic mill and associated worker housing on Yantic Street in Norwich, Connecticut. The 10 acre area includes a complex of mill buildings arrayed along the Yantic River, and a group of three brick mill worker houses. Today, Yantic Falls is part d...
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  • Glastonbury, Connecticut

    Hike the Cotton Hollow Nature Preserve

    5.0
    3 mi
    There are two parking locations for Cotton Hollow, the location tagged in the directions is the shortest hike to the old gun powder mill. Suggestions when it comes to exploring the preserve are to stay on the trails, know your limits, and enjoy! There are swimming holes along the river, but swim ...
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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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  • Simsbury, Connecticut

    Hike to the Heublein Tower on Talcott Mountain

    4.3
    2.54 mi / 404 ft gain
    The Heublien Tower Trail, located just inside the Talcott Mountain State Park entrance off of Route 185 in Simsbury CT, is a short 1.25 miles. While the hike isn't long, the first 1/3 of a mile is a steep incline that will get your heart pumping. The trail itself it very well kept, and although ...
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  • Ashburnham, Massachusetts

    Summit Mount Watatic via the Wapack Trail

    5.0
    3 mi / 800 ft gain
    Entering Mount Watatic in your GPS will take you to Rindge State Road (119), continue about two minutes down the road past where the GPS tells you. on the Right hand side you will will see a sign for Mount Watatic Parking area or just enter in coordinates: 42.696796, -71.904521 You will begin the...
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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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  • Granby, Connecticut

    Hiking Enders Falls

    4.0
    Enders State Forest sprawls over approximately 2000 acres, and is found within the towns of Granby and Barkhamsted in Connecticut.  Enders has a good sized parking lot directly on Route 219.  From the junction of Route 219 and Route 20, visitors will proceed west on Route 219 for 1.2 miles and tu...
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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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  • North Stonington, Connecticut

    Hike Wyassup Lake

    5.0
    2.4 mi / 278 ft gain
    Wyassup Lake is a 2.4 mile out and back hike that takes you past great forest setting located near North Stonington, Connecticut.
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  • Hopkinton, Rhode Island

    Hike to Long Pond & Ell Pond

    5.0
    5.7 mi
    Long & Ell Pond is a favorite hike at any time of the year, but it is not for the faint of heart (or small children)! The path immediately becomes more of a rock-scrambling adventure than a hike, but the views are so worth it.  This GPS address will lead you down a dirt road but you should ea...
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  • Concord, Massachusetts

    Hike around Walden Pond

    4.5
    1.69 mi / 45 ft gain
    Park in the lot ($8 for MA residents) by Walden Pond to access the trail, and head out either direction on the loop around the pond. Trail is accessible from April-October. 
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  • North Stonington, Connecticut

    Hike Narragansett Trail

    4.0
    10.7 mi / 1 ft gain
    Narragansett Trail is a 10.7 mile point-to-point hike that takes you by a lake located near North Stonington, Connecticut.
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