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The Best Hiking in Massachusetts

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

Top hiking spots in and near Massachusetts

  • Mount Washington, Massachusetts

    Explore Bash Bish Falls

    4.3
    1 mi
    One of my favorite walks to a spectacular falls. The trail is easy to follow and one mile from NY parking lot and 0.5 from the parking lot. The apparent place to swim. There are several very nice, family safe swimmable pools in the creek above and after the falls. There are signs at the top of t...
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  • Sutton, Massachusetts

    Hike the Purgatory Chasm Trail

    4.6
    1 mi / 115 ft gain
    For this 1-mile hike, you can park at the Purgatory Chasm Visitor Center. From there hit the trail and explore the unusual gap between the tall granite walls, which might be adorned with climbers. Great for all ages and dogs are welcome too. The trail is open March-November.
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  • Medford, Massachusetts

    Hike Southern Middlesex Fells Loop

    4.7
    3.5 mi / 756 ft gain
    Park in the parking area near Bellevue Pond. There are multiple entrances to the reservation (some closer to the reservoir itself than others). I have spent days in there hiking around and never seeing the water and there are days when I just hiked right in to the water and sat and enjoyed it. Th...
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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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  • Boston, Massachusetts

    Walk the 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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  • Milton, Massachusetts

    Hike the Great Blue Hill Trail

    5.0
    2.3 mi / 550 ft gain
    This is family-friendly hike takes you to nice views of Boston, after a moderately challenging stretch of elevation gain. Follow the blue markers along Great Blue Hill Trail to reach the observation tower. This is also a great spot for bird watching, and for exploring the nearby weather station.
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  • Newbury, Massachusetts

    Explore the Parker River National Wildlife Refuge

    4.6
    6.5 mi
    Located just north of Boston, Parker River National Wildlife Refuge was established in 1941 to provide feeding, resting, and nesting habitat for migratory birds. The refuge lands are both scenic and diverse, with approximately 4700 acres of habitats including sandy beach and dune, cranberry bog, ...
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  • Newbury, Massachusetts

    Hike the Hellcat Dunes Trail

    4.5
    0.7 mi / 16 ft gain
    Park in the parking area off of Refuge Rd. Take the Dunes Trail, a boardwalk path for the 0.7-mile loop. Enjoy the views from an observation deck on three-story-high dunes. This trail is accessible from April-October.
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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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  • Blackstone, Massachusetts

    Hike the Blackstone Gorge Trail

    0.7 mi / 72 ft gain
    Park at the lot at the corner of Staples Lane and County Street. From here you can access the Blackstone Gorge Trail. Dogs are allowed on leash, and you can enjoy various paths along the river or through the forest. At multiple points you can find yourself looking down at the Blackstone River fro...
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  • Dedham, Massachusetts

    Hike the Wilson Mountain Reservation Trail

    4.0
    2 mi
    This easy, well maintained trail has a little bit of everything you could need for a leisurely loop hike - bridges and streams, views of Boston, bird watching, and a dog-friendly policy (leash on).
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  • Adams, Massachusetts

    Hike Mount Greylock via Thunderbolt Trail

    3.5
    4.8 mi / 2275 ft gain
    This hike starts in Adams, Mass on Thiel Road. You can drive the road as far as you can until you reach a barrier. There is plenty of room to park off the road on both sides. You will walk he road for 0.5 miles until you meet the foot trail, marked as Thunderbolt.The Thunderbolt Ski trail was ...
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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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  • 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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  • Dartmouth, Massachusetts

    Hike Frank Knowles–Little River Reserve Trail

    4.3
    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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  • 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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