The Best Trails in Massachusetts (United States)

5,980 trails

(29)
Photo of Boston Freedom Trail (extended) Photo of Newton Highlands - Cutler Park Reservation Photo of 2017-07-23 ACROSS Lexington - Route H (LEXINGTON, MA - 麻州 勒克星顿)
  • Boston Freedom Trail (extended)

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    Hiking
    near Bay Village, Massachusetts (United States)
    Distance
    4.96mi
    Elevation +
    190f
    TrailRank
    66
    Photo of Boston Freedom Trail (extended) Photo of Boston Freedom Trail (extended) Photo of Boston Freedom Trail (extended)

    The Freedom Trail is a 2.5-mile-long path through downtown Boston, Massachusetts, that passes by 16 locations significant to the history of the United States. Marked largely with brick, it winds between Boston Common to ...

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  • near Newton Highlands, Massachusetts (United States)
    Distance
    10.63mi
    Elevation +
    269f
    TrailRank
    62
    Photo of Newton Highlands - Cutler Park Reservation Photo of Newton Highlands - Cutler Park Reservation Photo of Newton Highlands - Cutler Park Reservation

    Nice route reachable via public transportation starting from Newton Highlands to Cutler Park Reservation where we follow the Blue Heron Trail. On the way back you will pass in front of several restaurants, so it can be a...

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  • near Maple Grove, Massachusetts (United States)
    Distance
    5.69mi
    Elevation +
    2270f
    TrailRank
    62
    Photo of Maple Grove - Gould Rd - Bellows Parking Photo of Maple Grove - Gould Rd - Bellows Parking Photo of Maple Grove - Gould Rd - Bellows Parking

    Greylock Monument via Bellows and Thunderbolt Trails - easy to moderate for those who are fit. Difficult for anyone who is unprepared. Starts off easy enough on loose gravel, grass and eventually packed gravel before hit...

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  • near Winchester Highlands, Massachusetts (United States)
    Distance
    7.67mi
    Elevation +
    1129f
    TrailRank
    54| Rating 4.67
    Photo of Skyline loop trail at Middlesex Fells Reservation Photo of Skyline loop trail at Middlesex Fells Reservation Photo of Skyline loop trail at Middlesex Fells Reservation

    Loop trail with white trail markings. Plenty of street parking on weekends at the beginning/ending spot that I chose, but limited to 1 hour parking M-F 9:30am-5:30pm. You can also start and finish the loop from the main ...

    Well marked trail, with a variety of terrain. I would recommend to anyone that wants a 7+ mile hike in the woods
    mikescire
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  • near Eastham, Massachusetts (United States)
    Distance
    4.45nm
    Elevation +
    23f
    TrailRank
    50
    Photo of Kayaking the Eastham - Harwich Barrier Marshes Photo of Kayaking the Eastham - Harwich Barrier Marshes Photo of Kayaking the Eastham - Harwich Barrier Marshes

    7/21/2018 My first time to Cape Cod, Tim is the local and suggested kayaking this area. So I took my "marshing orders" from Tim. The Parking Lot now requires a parking sticker from the town which we had noticed $50. tick...

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  • OSD2M3

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    Baby Stroller
    near Goulding Village, Massachusetts (United States)
    Distance
    32.97mi
    Elevation +
    2756f
    TrailRank
    39
    Photo of OSD2M3 Photo of OSD2M3 Photo of OSD2M3

    Alternate waterfall ending , longer trip. Ends at campground/ lake reservations required .

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  • Jamaica Pond and Arnold Arboretum

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    Hiking
    near Jamaica Plain, Massachusetts (United States)
    Distance
    5.94mi
    Elevation +
    167f
    TrailRank
    38
    Photo of Jamaica Pond and Arnold Arboretum Photo of Jamaica Pond and Arnold Arboretum Photo of Jamaica Pond and Arnold Arboretum

    A beautiful walk in a very nice area of Boston. We visited two areas that are a short distance from each other, Jamaica Pond and the Arnold Arboretum. Beautiful homes on tree lined streets that lead you to an 80 acre ...

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  • David Sq to Middlesex Loop

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    Hiking
    near West Somerville, Massachusetts (United States)
    Distance
    13.73mi
    Elevation +
    436f
    TrailRank
    37
    Photo of David Sq to Middlesex Loop Photo of David Sq to Middlesex Loop Photo of David Sq to Middlesex Loop

    This route is accessible via public transportation. We start in Davis Sq. and go up to Middlesex Reservation, where we loop around the west side of the reservation. You will walk through Tufts University and Medford on y...

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  • Boston walking route

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    Walking
    near Back Bay, Massachusetts (United States)
    Distance
    7.21mi
    Elevation +
    95f
    TrailRank
    37
    Photo of Boston walking route Photo of Boston walking route Photo of Boston walking route

    Prudental - Back Bay - Newburry - Copley - Public Garden - Charles St - Beacon Hill - Boston Public Market - Financial District - Seaport District - Downtown - Boston Common

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  • BOSTON Bike EMERALD NECKLACE & CHARLES RIVER

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    Bicycle Touring
    near North End, Massachusetts (United States)
    Distance
    13.66mi
    Elevation +
    358f
    TrailRank
    37
    Photo of BOSTON Bike EMERALD NECKLACE & CHARLES RIVER Photo of BOSTON Bike EMERALD NECKLACE & CHARLES RIVER Photo of BOSTON Bike EMERALD NECKLACE & CHARLES RIVER

    Beware that our tour starts counter-traffic. It took us a few one-way roads before adapting the tour provided by the bike rental. Bike rental: Urban aventure tour 103 Atlantic Avenue Boston, MA 02110, United States...

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  • Cape Cod Great Island Trail

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    Hiking
    near Mayo Beach, Massachusetts (United States)
    Distance
    6.14mi
    Elevation +
    358f
    TrailRank
    36
    Photo of Cape Cod Great Island Trail Photo of Cape Cod Great Island Trail Photo of Cape Cod Great Island Trail

    The access to Jeremy Point was closed to protect birds nesting at this period. Beware the tans in June and July (edit) Tips: Great Island Trail: From route 6, follow signs to Welfleet Center, turn left onto East ...

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  • Hale and Noanet half

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    Trail Running
    near Dover, Massachusetts (United States)
    Distance
    14.02mi
    Elevation +
    899f
    TrailRank
    34| Rating 4.33
    Photo of Hale and Noanet half Photo of Hale and Noanet half Photo of Hale and Noanet half

    Hale and Noanet are two connected reservations. I also briefly touch on the Powisset Farm grounds. There are so many routes and paths here that it is easy to take a wrong turn. Luckily, most 'wrong' turns just bring you ...

    Nice trail, it might be a bit muddy after rain
    Sybren Bouwman
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  • near East Fairhaven, Massachusetts (United States)
    Distance
    2.61mi
    Elevation +
    0f
    TrailRank
    34
    Photo of Shaw Farm Trail (Mattapoisett, MA) Photo of Shaw Farm Trail (Mattapoisett, MA) Photo of Shaw Farm Trail (Mattapoisett, MA)

    Shaw Farm Trail partially within the Nasketucket Bay State Reservation. Leveled terrain. The path to the shoreline it's composed by different trails. There is more than one path, and they are all well signed. Here I chos...

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  • Plymouth - Boston

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    Hiking
    near Plymouth, New Hampshire (United States)
    Distance
    118.16mi
    Elevation +
    2503f
    TrailRank
    33
    Photo of Plymouth - Boston Photo of Plymouth - Boston Photo of Plymouth - Boston

    Car, train, walk: took about 3:15 with a couple stops. No parking in Wilmington, but Anderson RTC is only about 15 minutes drive south. Anderson RTC had plenty of parking.

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  • NET Notch to Skinner State Park

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    Walking
    near Aldrich Mills, Massachusetts (United States)
    Distance
    5.41mi
    Elevation +
    1778f
    TrailRank
    33
    Photo of NET Notch to Skinner State Park Photo of NET Notch to Skinner State Park Photo of NET Notch to Skinner State Park

    This is a well used trail that is in the process of being restored and repaired. Even with this work taking place it is highly recommended. The trail is physically challenging due to is short but steep up and down terrai...

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  • near Sharon Heights, Massachusetts (United States)
    Distance
    6.29mi
    Elevation +
    1007f
    TrailRank
    32
    Photo of Bay Circuit Trail - Sharon - Walpole Photo of Bay Circuit Trail - Sharon - Walpole Photo of Bay Circuit Trail - Sharon - Walpole

    Bay Circuit Trail from Walpole St in Sharon to Main St in Walpole. Trail climbs Pierce Hill off Walpole St. Fairly steep climb but short. Top of hill has a small rocky section. After descending the hill trail follows ...

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  • Mystic River Race 5/18/2014

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    Kayak\/Canoe
    near Ten Hills, Massachusetts (United States)
    Distance
    9.73nm
    Elevation +
    161f
    TrailRank
    32
    Photo of Mystic River Race 5/18/2014 Photo of Mystic River Race 5/18/2014 Photo of Mystic River Race 5/18/2014

    11.2 statute miles. Two relatively easy portages with slight grades to exit and enter the water. All three boats in the sea kayak class beat last years winning time. Before I had been there I figured it would be noisy...

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