Best Trails of Massachusetts

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

  • #1 Blue Hills Reservation

    9 Reviews

    Milton, MA

    At this 7,000-acre open space south of Boston proper, some 100 miles of interlocking trails offer visitors a plethora of hike options. The skyline hills prove natural destinations and centerpieces ...
    •  4.5 miles
    •  Guide

    At this 7,000-acre open space south of Boston proper, some 100 miles of interlocking trails offer visitors a plethora of ...

  • #2 Lincoln Conservation Land (Mount Misery)

    8 Reviews

    Lincoln, MA

    The Mount Misery conservation land provides excellent views of the Sudbury River and Fairhaven Bay, while passing through a deeply shaded hemlock forest and a patch of open marsh. Wildlife flourishes ...
    •  1.5 hours
    •  3 miles
    •  Guide

    The Mount Misery conservation land provides excellent views of the Sudbury River and Fairhaven Bay, while passing through ...

  • #3 Bash-Bish and Alander Mountains

    10 Reviews

    Mount Washington, MA

    A hard hike over secluded terrain and long stretches of open ridge to perhaps the very best view in the Berkshires. In a region known for spectacular views, the hike along the summit ridge of ...
    •  6 hours
    •  5.6 miles
    •  Guide

    A hard hike over secluded terrain and long stretches of open ridge to perhaps the very best view in the Berkshires. In a ...

  • #4 Duxbury Bay and Back River

    1 Reviews

    Duxbury, MA

    Duxbury Bay is an extraordinarily lovely place to paddle. The bay and tidal rivers of the Great Salt Marsh offer exceptional natural beauty and serenity. Duxbury’s seven-mile-long barrier beach ...
    •  Day trip
    •  11 miles
    •  Guide

    Duxbury Bay is an extraordinarily lovely place to paddle. The bay and tidal rivers of the Great Salt Marsh offer exceptional ...

  • #5 Appalachian National Scenic Trail: CT & MA

    4 Reviews

    North Adams, MA

    This 2,155-mile national scenic trail, journeying from Springer Mountain, Georgia to Mount Katahdin, Maine, traverses the northwest corner of Connecticut and western Massachusetts, touring forest, ...
    •  138 miles
    •  Guide

    This 2,155-mile national scenic trail, journeying from Springer Mountain, Georgia to Mount Katahdin, Maine, traverses the ...

  • #6 Mount Greylock

    4 Reviews

    Adams, MA

    Mount Greylock is a fascinating place to explore—from endangered plants and animals to travels with Thoreau. This highest peak in Massachusetts has something memorable for everyone. Mount Greylock ...
    •  2 hours
    •  2.2 miles
    •  Guide

    Mount Greylock is a fascinating place to explore—from endangered plants and animals to travels with Thoreau. This highest ...

  • #7 Metacomet-Monadnock Trail, Holyoke Range

    4 Reviews

    South Hadley, MA

    Five miles north of South Hadley. This fragment of the long-distance Metacomet-Monadnock(M-M) Trail offers a rolling ridge tour, with both challenging and comfortable stretches. It tags bald ...
    •  9 miles
    •  Guide

    Five miles north of South Hadley. This fragment of the long-distance Metacomet-Monadnock(M-M) Trail offers a rolling ridge ...

  • #8 Mount Toby State Reservation

    4 Reviews

    Amherst, MA

    Ten miles north of Amherst. Traveling part of the Robert Frost Trail and Summit Road (a restricted road closed to vehicles), this loop explores rich woods and obtains a summit panorama sweeping ...
    •  5.5 miles
    •  Guide

    Ten miles north of Amherst. Traveling part of the Robert Frost Trail and Summit Road (a restricted road closed to vehicles), ...

  • #9 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 ...

  • #10 Blue Hills

    3 Reviews

    Milton, MA

    The Blue Hills Reservation is one of the premiere mountain biking areas in Eastern Massachusetts because of its extensive trail system and varied terrain. Bordered by six cities and towns, the ...
    •  30 minutes
    •  3.8 miles
    •  Guide

    The Blue Hills Reservation is one of the premiere mountain biking areas in Eastern Massachusetts because of its extensive ...

  • #11 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 ...

  • #12 Gates Pond

    1 Reviews

    Berlin, MA

    Finding a lake left in its natural state is rare indeed here in eastern Massachusetts. Here’s a pond that doesn’t have a single cottage on its shoreline, and the trail that circles it is open ...
    •  1 hour
    •  2.5 miles
    •  Guide

    Finding a lake left in its natural state is rare indeed here in eastern Massachusetts. Here’s a pond that doesn’t have a ...

  • #13 Holyoke Range State Park

    4 Reviews

    Amherst, MA

    The town of Amherst is about 6 miles east of Interstate 91, 10 miles east of Northhampton, and 95 miles west of Boston. Expect rolling terrain, with regular, short, sometimes steep, climbs and ...
    •  10 miles
    •  Guide

    The town of Amherst is about 6 miles east of Interstate 91, 10 miles east of Northhampton, and 95 miles west of Boston. Expect ...

  • #14 Connecticut River: Riverview Picnic Area to Barton Cove

    3 Reviews

    Northfield, MA

    The trip between Riverview Picnic Area and Barton Cove is an especially nice paddle, in part because the river changes moods, from wide and lazy to deep and narrow. Along the way you will pass ...
    •  Day use, camping available
    •  5.3 miles
    •  Guide

    The trip between Riverview Picnic Area and Barton Cove is an especially nice paddle, in part because the river changes moods, ...

  • #15 Wompatuck State Park

    4 Reviews

    Hingham, MA

    This ride was developed on the route of a race that took place in the park during the summer of 1996. The race has since moved on, giving this trail a chance to recover. You should expect numerous ...
    •  1.5 hours
    •  9.6 miles
    •  Guide

    This ride was developed on the route of a race that took place in the park during the summer of 1996. The race has since ...

  • #16 Lowell-Dracut-Tyngsboro State Park

    3 Reviews

    Lowell, MA

    Just north of Lowell, off Massachusetts Highway 113, and 30 miles north of Boston. The terrain is relatively flat, with a few short climbs. Yield to the occasional horseback rider.
    •  15 miles
    •  Guide

    Just north of Lowell, off Massachusetts Highway 113, and 30 miles north of Boston. The terrain is relatively flat, with a ...

  • #17 Cape Cod Rail Trail

    12 Reviews

    Nickerson State Park, MA

    Cape Cod Rail Trail is a hiking and biking trail in Barnstable County, Massachusetts. It is within Cape Cod Rail Trail and Nickerson State Park. It is 16.6 miles long and begins at 113 feet altitude. ...
    •  16.6 miles

    Cape Cod Rail Trail is a hiking and biking trail in Barnstable County, Massachusetts. It is within Cape Cod Rail Trail and ...

  • #18 Cape Ann Cruise

    3 Reviews

    Gloucester, MA

    This ride explores Boston's North Shore. The shorter 22-mile loop circles the rocky shores of Cape Ann, where fishermen's cottages and grand summer homes now share the ocean views. The route ...
    •  36.4 miles
    •  Guide

    This ride explores Boston's North Shore. The shorter 22-mile loop circles the rocky shores of Cape Ann, where fishermen's ...

  • #19 Blackstone River and Canal Heritage

    2 Reviews

    Uxbridge, MA

    East of Massachusetts 122 in Uxbridge and Northbridge. Two hikes explore the park, traveling multiple-use trails: The Towpath Hike tours a scenic, mostly natural corridor through the old industrial ...
    •  8 miles
    •  Guide

    East of Massachusetts 122 in Uxbridge and Northbridge. Two hikes explore the park, traveling multiple-use trails: The Towpath ...

  • #20 Jamaica Pond

    3 Reviews

    Brookline, MA

    An easy recreational trail offers a popular and pleasant circuit around historic Jamaica Pond.
    •  45 minutes
    •  1.5 miles
    •  Guide

    An easy recreational trail offers a popular and pleasant circuit around historic Jamaica Pond.