Best Hiking in Massachusetts

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

  • #1 Blue Hills Reservation

    10 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)

    9 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 Mount Greylock

    5 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 ...

  • #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 Toby State Reservation

    5 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), ...

  • #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 Gates Pond

    2 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 ...

  • #9 Mount Watatic Trail

    3 Reviews

    Winchendon, MA

    A not-too-tough climb to the top of Mount Watatic in Ashburnham will give kids the opportunity to do some safe summit exploring (there is no danger of them toppling off a cliff) while adults ...
    •  2.5 hours
    •  3 miles
    •  Guide

    A not-too-tough climb to the top of Mount Watatic in Ashburnham will give kids the opportunity to do some safe summit exploring ...

  • #10 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 ...

  • #11 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.

  • #12 Monument Mountain

    4 Reviews

    Great Barrington, MA

    The signature Berkshire hike featuring spectacular cliffs, breathtaking views, history, and ever-present raptors soaring overhead. Over the past few years the trail system at Monument Mountain ...
    •  2.5 hours
    •  2.4 miles
    •  Guide

    The signature Berkshire hike featuring spectacular cliffs, breathtaking views, history, and ever-present raptors soaring ...

  • #13 Mount Tom State Reservation - Dinosaur Footprints Reservation

    3 Reviews

    Northampton, MA

    West bank of the Connecticut River at Northampton. Three short hikes present the appeal of these two reservations. Special attractions: vistas, Triassic-period dinosaur footprints, floral fossils, ...
    •  4.5 miles
    •  Guide

    West bank of the Connecticut River at Northampton. Three short hikes present the appeal of these two reservations. Special ...

  • #14 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 ...

  • #15 Mount Greylock State Reservation

    7 Reviews

    Williamstown, MA

    In the rolling hillscape of western Massachusetts, 3,491-foot Mount Greylock stands alone, an isolated massif carved by deep valleys and awash with diverse flora. A loop around the peak, ...
    •  1-2 Days
    •  11 miles
    •  Guide

    In the rolling hillscape of western Massachusetts, 3,491-foot Mount Greylock stands alone, an isolated massif carved by ...

  • #16 Hancock Shaker Village Trail

    5 Reviews

    Pittsfield, MA

    Five miles west of Pittsfield. Constructed and maintained by the Boy Scouts of America, this circuit travels wooded, stream, and hilltop sites key to a 19th-cintury Shaker society. The tour ...
    •  6.5 miles
    •  Guide

    Five miles west of Pittsfield. Constructed and maintained by the Boy Scouts of America, this circuit travels wooded, stream, ...

  • #17 Chester-Blandford State Forest

    4 Reviews

    Chester, MA

    The Westfield River begins as three streams draining the eastern slope of the Berkshire Hills, and then flows into the Connecticut River at Agawam. State highways and railroads run parallel along ...
    •  3 hours
    •  7.1 miles
    •  Guide

    The Westfield River begins as three streams draining the eastern slope of the Berkshire Hills, and then flows into the Connecticut ...

  • #18 Skinner State Park

    1 Reviews

    Northampton, MA

    The Holyoke Range, including Skinner State Park and the adjacent Holyoke Range State Park, is one of the only east–west mountain ranges in the country—most others run north–south. This hike ...
    •  3 hours
    •  4.7 miles
    •  Guide

    The Holyoke Range, including Skinner State Park and the adjacent Holyoke Range State Park, is one of the only east–west mountain ...

  • #19 Mount Grace State Forest

    3 Reviews

    Warwick, MA

    With a tall, eight-platform fire tower at its peak and the long-distance Metacomet- Monadnock (M-M) Trail running up its flank, Mount Grace deserves more attention than it gets. But located ...
    •  2 hours
    •  4.2 miles
    •  Guide

    With a tall, eight-platform fire tower at its peak and the long-distance Metacomet- Monadnock (M-M) Trail running up its ...

  • #20 Elm Bank Reservation

    1 Reviews

    Wellesley, MA

    Don’t let the soccer fields fool you; this reservation has miles of hiking trails through a forest that borders the Charles River. The fact that up until recently these wild acres could have ...
    •  0.75 to 1 hour
    •  2 miles
    •  Guide

    Don’t let the soccer fields fool you; this reservation has miles of hiking trails through a forest that borders the Charles ...