Best Walking in Massachusetts

This list represents the most popular walking in Massachusetts. Use this list to plan your next Massachusetts walking trip. Select a state and/or activity below to find even more top trails.

  • #1 World's End Reservation

    3 Reviews

    Hingham, MA

    World’s End: what a great name. And what a great place. Should a visitor to eastern Massachusetts have time to visit only one natural area, I would recommend World’s End. In my opinion this is ...
    •  3 hours
    •  4.5 miles
    •  Guide

    World’s End: what a great name. And what a great place. Should a visitor to eastern Massachusetts have time to visit only ...

  • #2 Minuteman Bikeway

    5 Reviews

    Arlington, MA

    The Minuteman Bikeway has it all. It’s close to Boston, it’s historic, it’s located in a lush and beautiful area, and it’s great for families. Its historical significance is of particular note. ...
    •  11 miles
    •  Guide

    The Minuteman Bikeway has it all. It’s close to Boston, it’s historic, it’s located in a lush and beautiful area, and it’s ...

  • #3 Falmouth Shining Sea Path

    2 Reviews

    Falmouth, MA

    Enjoy the brilliant views of the Nantucket and Vineyard Sounds on this short trail connecting Falmouth and Woods Hole. Surface: Asphalt. Location: Barnstable County.
    •  4 miles
    •  Guide

    Enjoy the brilliant views of the Nantucket and Vineyard Sounds on this short trail connecting Falmouth and Woods Hole. Surface: ...

  • #4 Wachusett Reservoir

    1 Reviews

    Boylston, MA

    Wachusett Reservoir was created in 1895 to solve the water needs of the greater Boston area. Today, the reservoir still supplies water to Boston (with the help of Quabbin Reservoir), but it also ...
    •  Guide

    Wachusett Reservoir was created in 1895 to solve the water needs of the greater Boston area. Today, the reservoir still supplies ...

  • #5 Alander Mountain Trail

    8 Reviews

    Mount Washington, MA

    Alander Mountain Trail is a hiking trail in Mount Washington, Massachusetts. It is 2.6 miles long and begins at 1,651 feet altitude. Traveling the entire trail is 5.3 miles with a total elevation ...
    •  2.6 miles

    Alander Mountain Trail is a hiking trail in Mount Washington, Massachusetts. It is 2.6 miles long and begins at 1,651 feet ...

  • #6 Along the Charles River: Boston - Cambridge

    0 Reviews

    Boston, MA

    The Charles River is beautiful, historic, conveniently located, and great people-watching territory. Sunsets over the river from Boston are often beautiful. Early mornings are special, too. Sail ...
    •  1.8 hours
    •  3.75 miles
    •  Guide

    The Charles River is beautiful, historic, conveniently located, and great people-watching territory. Sunsets over the river ...

  • #7 Lexington, Lincoln, and Concord along the Minute Man Trail

    0 Reviews

    Lexington, MA

    The battles of Lexington and Concord began the American Revolution. See where much of the action happened, visit restored colonial-era buildings, cross boardwalks over marshy wildlife sanctuaries, ...
    •  2.5 hours
    •  5 miles
    •  Guide

    The battles of Lexington and Concord began the American Revolution. See where much of the action happened, visit restored ...

  • #8 Moose Hill Wildlife Sanctuary

    1 Reviews

    Sharon, MA

    Have you ever longed to find some secluded hilltop and just sit peacefully, letting the breeze and quietness lull your senses? I have, and Moose Hill Wildlife Sanctuary in Sharon has one of the ...
    •  2.5 to 3 hours
    •  4.25 miles
    •  Guide

    Have you ever longed to find some secluded hilltop and just sit peacefully, letting the breeze and quietness lull your senses? ...

  • #9 Southwest Corridor Park, Boston

    0 Reviews

    Boston, MA

    The southwest corridor park was almost a highway. On this walk you can see what happened when the expressway plan was dropped, the narrow corridor became transit lines, and a park was built around ...
    •  3 hours
    •  4.5 miles
    •  Guide

    The southwest corridor park was almost a highway. On this walk you can see what happened when the expressway plan was dropped, ...

  • #10 Upper Charles River Reservation, Boston

    1 Reviews

    Newton, MA

    A natural and wild quality pervades the Charles River’s banks upriver from the dam at Watertown Square. Unlike the riverbanks along the Charles River Basin—the well-known Boston and Cambridge ...
    •  5 hours
    •  6 miles
    •  Guide

    A natural and wild quality pervades the Charles River’s banks upriver from the dam at Watertown Square. Unlike the riverbanks ...

  • #11 Bash Bish Trail

    7 Reviews

    Bash Bish Falls State Park, MA

    Bash Bish Trail is a hiking trail in Mount Washington, Massachusetts. It is within Bashbish Falls State Park and Bash Bish Falls State Park. It is 0.4 miles long and begins at 1,275 feet altitude. ...
    •  0.4 miles

    Bash Bish Trail is a hiking trail in Mount Washington, Massachusetts. It is within Bashbish Falls State Park and Bash Bish ...

  • #12 Race Brook Trail

    6 Reviews

    Berkshire County, MA

    Race Brook Trail is a hiking trail in Berkshire County, Massachusetts. It is 1.8 miles long and begins at 763 feet altitude. Traveling the entire trail is 3.7 miles with a total elevation gain ...
    •  1.8 miles

    Race Brook Trail is a hiking trail in Berkshire County, Massachusetts. It is 1.8 miles long and begins at 763 feet altitude. ...

  • #13 Hull Peninsula, Boston

    1 Reviews

    Hull, MA

    One of Boston's best-kept secrets is the pleasure of walking the Hull peninsula—a long stretch of shoreline and flat, sandy public beach that welcomes discovery. The town’s relative isolation ...
    •  4 hours
    •  6.5 miles
    •  Guide

    One of Boston's best-kept secrets is the pleasure of walking the Hull peninsula—a long stretch of shoreline and flat, sandy ...

  • #14 Marblehead Rail-Trail

    0 Reviews

    Marblehead, MA

    Marblehead is one of the nicest beach communities north of Boston. This trail forks in two directions. Both branches are pretty, and both eventually lead to the Atlantic Ocean. The charm of ...
    •  5 miles
    •  Guide

    Marblehead is one of the nicest beach communities north of Boston. This trail forks in two directions. Both branches are ...

  • #15 Norwottuck Rail Trail (Francis P. Ryan Section)

    6 Reviews

    Northampton, MA

    Norwottuck Rail Trail (Francis P. Ryan Section) is a hiking and biking trail in Northampton, Massachusetts. It is 2.6 miles long and begins at 146 feet altitude. Traveling the entire trail is ...
    •  2.6 miles

    Norwottuck Rail Trail (Francis P. Ryan Section) is a hiking and biking trail in Northampton, Massachusetts. It is 2.6 miles ...

  • #16 Arlington, outside Boston

    0 Reviews

    Arlington, MA

    At first glance Arlington seems to be one more pleasant suburb of Boston—a good place to live without much for visitors to see. Not so. The town played a pivotal role in the American Revolution, ...
    •  4 hours
    •  5 miles
    •  Guide

    At first glance Arlington seems to be one more pleasant suburb of Boston—a good place to live without much for visitors to ...

  • #17 Deer Island, Boston

    0 Reviews

    Boston, MA

    From a high hill on Deer Island, dramatic views spread out across Boston Harbor. You can see Boston’s sparkling skyline, lighthouses near and far, the harbor’s twenty-nine other islands, a new ...
    •  1.5 hours
    •  2.6 miles
    •  Guide

    From a high hill on Deer Island, dramatic views spread out across Boston Harbor. You can see Boston’s sparkling skyline, ...

  • #18 Southwest Corridor

    0 Reviews

    Boston, MA

    This urban rail-trail takes you from downtown Boston to Jamaica Plain. It is used by bicyclists commuting to and from downtown and by outdoor enthusiasts looking for some fun in the sun near ...
    •  5 miles
    •  Guide

    This urban rail-trail takes you from downtown Boston to Jamaica Plain. It is used by bicyclists commuting to and from downtown ...

  • #19 Neponset River and Ashmont Hill, Boston

    1 Reviews

    Boston, MA

    A quiet river flows through a widening estuary to Boston Harbor, past riverfront communities and a public beach. This river—the Neponset—is a little-known sister of the larger Charles River. ...
    •  1 - 3 hours
    •  2 miles
    •  Guide

    A quiet river flows through a widening estuary to Boston Harbor, past riverfront communities and a public beach. This river—the ...

  • #20 Downtown and Back Bay, Boston Marathon

    1 Reviews

    Boston, MA

    This walk takes you to the several historic finish lines of the Boston Marathon and by marathon memorabilia and monuments through the lovely streets of Back Bay. Start at Eliot Hotel on Ma ...
    •  30 minutes
    •  0.8 miles
    •  Guide

    This walk takes you to the several historic finish lines of the Boston Marathon and by marathon memorabilia and monuments ...