Hiking

The Best Hiking Trails in Massachusetts (United States)

1,760 trails

(25)
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

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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

  • 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
    51
    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 ...

  • 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...

  • Cape Cod Great Island Trail

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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

  • Shaw Farm Trail (Mattapoisett, MA)

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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...

  • 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.

  • 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 ...

  • Blue Hills Reservation MA

    Hiking
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    near Camp Sayre, Massachusetts (United States)
    Author
    fredshirley
    Distance
    3.82mi
    Elevation +
    2057f
    TrailRank
    29| Rating 3.0
    Photo ofBlue Hills Reservation MA

    We hiked a section of Blue Hills Reservation in eastern Massachusetts, going over five small mountains: Hancock Hill, Hemenway Hill, Wolcott Hill, Great Blue Hill and Houghton Hill. Click "View more" below for hike info...

    Skyline Trail up & back well marked
    DSonifer01

  • Alander/South Taconic/Ashley trail loop

    Hiking
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    near Alander, Massachusetts (United States)
    Author
    psychonaut7
    Distance
    10.81mi
    Elevation +
    1959f
    TrailRank
    29
    Photo ofAlander/South Taconic/Ashley trail loop Photo ofAlander/South Taconic/Ashley trail loop Photo ofAlander/South Taconic/Ashley trail loop

    Alander/South Taconic/Ashley trail loop - This loop starts at the Mt. Washington State Forest H.Q. The trails are for the most part pretty flat and quite forgiving to those who want to do some trail running.

  • Pumps pond to vale reservation

    Hiking
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    near Andover, Massachusetts (United States)
    Author
    Rachel Scaer
    Distance
    6.38mi
    Elevation +
    141f
    TrailRank
    28
    Photo ofPumps pond to vale reservation Photo ofPumps pond to vale reservation Photo ofPumps pond to vale reservation

    From hidden meadow road walk through the reservation, then take the nature trail around foster pond to vale reservation.

  • Red Trail Frank Knowles/ Little River Reserve (Dartmouth, MA)

    Hiking
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    near Cranberry Bog Corner, Massachusetts (United States)
    Author
    Dantecn
    with fe.vilela
    Distance
    2.18mi
    Elevation +
    23f
    TrailRank
    27
    Photo ofRed Trail Frank Knowles/ Little River Reserve (Dartmouth, MA) Photo ofRed Trail Frank Knowles/ Little River Reserve (Dartmouth, MA) Photo ofRed Trail Frank Knowles/ Little River Reserve (Dartmouth, MA)

    Red Trail of the Frank Knowles/ Little River Reserve. End of winter 2019; Trailhead at the parking lot of Potomska Road. 7km hike on even terrain, with boardwalks to cross over beautiful salt marshes plains. Beware hunti...

  • Blue Hills Hike 08.05.24

    Hiking
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    near North Randolph, Massachusetts (United States)
    Author
    robca2
    Distance
    4.08mi
    Elevation +
    699f
    TrailRank
    27
    Photo ofBlue Hills Hike 08.05.24

    We hiked the eastern Blue Hills reservation, hitting intersections 3013 -> 3030 -> 3044 -> 3073 -> 3121 -> 3111 -> 3090 -> 3042.

  • Mt Tom - M&M Trail

    Hiking
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    near Smiths Ferry, Massachusetts (United States)
    Author
    JCE
    with fredshirley
    Distance
    4.77mi
    Elevation +
    1106f
    TrailRank
    27

    Nice hike with some great views from rocky ridge points. The views are mostly of populated areas, due to its location. That said, if you're in the area this is a really nice hike to do. The hike, which follows a fa...

  • Smiths Ferry mt tom

    Hiking
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    near Smiths Ferry, Massachusetts (United States)
    Author
    mikerobi
    Distance
    4.95mi
    Elevation +
    1099f
    TrailRank
    27
    Photo ofSmiths Ferry mt tom Photo ofSmiths Ferry mt tom Photo ofSmiths Ferry mt tom

    From goats peak to cell tower along ridge. Multiple overlooks of Easthamptpn, Mass with great picnic spots!

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