The Best Trails in Massachusetts (United States)

6,010 trails

(36)
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)
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  • Boston Freedom Trail (extended)

    Hiking
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    near Bay Village, Massachusetts (United States)
    Author
    alperdace
    Distance
    4.96mi
    Elevation +
    190f
    TrailRank
    69
    Photo ofBoston Freedom Trail (extended) Photo ofBoston Freedom Trail (extended) Photo ofBoston 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 ...

  • Newton Highlands - Cutler Park Reservation

    Hiking
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    near Newton Highlands, Massachusetts (United States)
    Author
    Jose A. Ruipérez
    Distance
    10.63mi
    Elevation +
    269f
    TrailRank
    62
    Photo ofNewton Highlands - Cutler Park Reservation Photo ofNewton Highlands - Cutler Park Reservation Photo ofNewton 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...

  • Maple Grove - Gould Rd - Bellows Parking

    Hiking
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    near Maple Grove, Massachusetts (United States)
    Author
    Dena Brayson
    Distance
    5.69mi
    Elevation +
    2270f
    TrailRank
    62
    Photo ofMaple Grove - Gould Rd - Bellows Parking Photo ofMaple Grove - Gould Rd - Bellows Parking Photo ofMaple 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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  • Skyline loop trail at Middlesex Fells Reservation

    Hiking
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    near Winchester Highlands, Massachusetts (United States)
    Author
    MTols
    Distance
    7.67mi
    Elevation +
    1129f
    TrailRank
    55| Rating 4.67
    Photo ofSkyline loop trail at Middlesex Fells Reservation Photo ofSkyline loop trail at Middlesex Fells Reservation Photo ofSkyline 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

  • Kayaking the Eastham - Harwich Barrier Marshes

    Kayak\/Canoe
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    near Eastham, Massachusetts (United States)
    Author
    jmmdds
    Distance
    4.45nm
    Elevation +
    23f
    TrailRank
    50
    Photo ofKayaking the Eastham - Harwich Barrier Marshes Photo ofKayaking the Eastham - Harwich Barrier Marshes Photo ofKayaking 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...

  • Jamaica Pond and Arnold Arboretum

    Hiking
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    near Jamaica Plain, Massachusetts (United States)
    Author
    Port flora
    with maxini2001
    Distance
    5.94mi
    Elevation +
    167f
    TrailRank
    50
    Photo ofJamaica Pond and Arnold Arboretum Photo ofJamaica Pond and Arnold Arboretum Photo ofJamaica 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 ...

  • OSD2M3

    Baby Stroller
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    near Goulding Village, Massachusetts (United States)
    Author
    joshua d ensling
    Distance
    32.97mi
    Elevation +
    2756f
    TrailRank
    40
    Photo ofOSD2M3 Photo ofOSD2M3 Photo ofOSD2M3

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

  • David Sq to Middlesex Loop

    Hiking
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    near West Somerville, Massachusetts (United States)
    Author
    Jose A. Ruipérez
    Distance
    13.73mi
    Elevation +
    436f
    TrailRank
    37
    Photo ofDavid Sq to Middlesex Loop Photo ofDavid Sq to Middlesex Loop Photo ofDavid 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...

  • Boston walking route

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

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

  • BOSTON Bike EMERALD NECKLACE & CHARLES RIVER

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

  • Cape Cod Great Island Trail

    Hiking
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    near Mayo Beach, Massachusetts (United States)
    Author
    candeur
    Distance
    6.14mi
    Elevation +
    358f
    TrailRank
    37| Rating 4.33
    Photo ofCape Cod Great Island Trail Photo ofCape Cod Great Island Trail Photo ofCape 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 ...

    Entorno paradisiaco
    luis_padura

  • Hale and Noanet half

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

  • Shaw Farm Trail (Mattapoisett, MA)

    Hiking
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    near East Fairhaven, Massachusetts (United States)
    Author
    Dantecn
    Distance
    2.61mi
    Elevation +
    0f
    TrailRank
    34
    Photo ofShaw Farm Trail (Mattapoisett, MA) Photo ofShaw Farm Trail (Mattapoisett, MA) Photo ofShaw 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...

  • Bay Village - Chinatown/Leather District

    Car
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    near Bay Village, Massachusetts (United States)
    Author
    avenson
    Distance
    59.32mi
    Elevation +
    1010f
    TrailRank
    34
    Photo ofBay Village - Chinatown/Leather District Photo ofBay Village - Chinatown/Leather District Photo ofBay Village - Chinatown/Leather District

    Grayline bus tour. MIT, Cambridge, Paul Revere Boston Tea Party, 1794 USA Constitution, downtown Boston Sept 19 2018

  • Plymouth - Boston

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

  • NET Notch to Skinner State Park

    Walking
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    near Aldrich Mills, Massachusetts (United States)
    Author
    ljrlongfield@gmail.com
    Distance
    5.41mi
    Elevation +
    1778f
    TrailRank
    33
    Photo ofNET Notch to Skinner State Park Photo ofNET Notch to Skinner State Park Photo ofNET 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...

  • Pocumtuck Ridge Trail- south sugarloaf to poet's seat tower

    Hiking
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    near Sunderland, Massachusetts (United States)
    Author
    Jon Dinsmore
    Distance
    15.23mi
    Elevation +
    2444f
    TrailRank
    32
    Photo ofPocumtuck Ridge Trail- south sugarloaf to poet's seat tower Photo ofPocumtuck Ridge Trail- south sugarloaf to poet's seat tower Photo ofPocumtuck Ridge Trail- south sugarloaf to poet's seat tower

    Pocumtuck Ridge Trail- south sugarloaf to poet's seat tower Well blazed and not too strenuous. I've marked as moderate more for length than for any kind of technical difficulty. The one bad part is that between kee...

  • Bay Circuit Trail - Sharon - Walpole

    Hiking
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    near Sharon Heights, Massachusetts (United States)
    Author
    ksizzo
    Distance
    6.29mi
    Elevation +
    1007f
    TrailRank
    32
    Photo ofBay Circuit Trail - Sharon - Walpole Photo ofBay Circuit Trail - Sharon - Walpole Photo ofBay 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 ...

  • Mystic River Race 5/18/2014

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