Massachusetts - Outdoor Activities

Massachusetts has approximately 2,836 trails, including 2,051 hiking trails and 1,503 for walking. These trails range from 0 to 383 miles in length. The most popular trails are Alander Mountain Loop, Blue Hills Reservation and Appalachian National Scenic Trail: CT & MA. The last Trails.com member to complete a trail in Massachusetts was Sara B. who completed Gates Pond.

  • Cape Cod Rail-TrailView Trail Details

    11 Reviews

    Harwich, MA

    •  26 miles
    •  Guide

    Among the most scenic recreation trails in Massachusetts and a favorite with cyclists and day hikers, the Cape Cod Trail provides access to beaches, ...

  • Bash-Bish and Alander MountainsView Trail Details

    10 Reviews

    Mount Washington, MA

    • Hiking  
    •  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 region known for spectacular ...

  • Blue Hills ReservationView Trail Details

    9 Reviews

    Milton, MA

    • Hiking  
    •  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 hike options. The skyline ...

  • Alander Mountain LoopView Trail Details

    8 Reviews

    South Egremont, MA

    • Hiking  
    •  15 miles
    •  Guide

    The southwest corner of Massachusetts on the tri-state border of MA, CT, and NY. In Mount Washington State Forest, this demanding all-day or ...

  • Lincoln Conservation Land (Mount Misery)View Trail Details

    8 Reviews

    Lincoln, MA

    • Hiking  
    •  1.5 hours
    •  3 miles
    •  Guide

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

  • Mount Greylock State ReservationView Trail Details

    7 Reviews

    Williamstown, MA

    •  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 deep valleys and ...

  • Race Brook Falls and Mount EverettView Trail Details

    6 Reviews

    Sheffield, MA

    • Hiking  
    •  6 hours
    •  5.4 miles
    •  Guide

    A daylong adventure to mountain cascades and up rocky windswept ridges to the very top of the southern Berkshires. This is not a particularly ...

  • Minuteman BikewayView Trail Details

    5 Reviews

    Arlington, MA

    •  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 great for families. ...

  • Hancock Shaker Village TrailView Trail Details

    5 Reviews

    Pittsfield, MA

    • Hiking  
    •  6.5 miles
    •  Guide

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

  • Holyoke Range State ParkView Trail Details

    4 Reviews

    Amherst, MA

    • Mountain Biking  
    •  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 rolling terrain, ...

  • Wompatuck State ParkView Trail Details

    4 Reviews

    Hingham, MA

    • Mountain Biking  
    •  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 moved on, giving this ...

  • Appalachian National Scenic Trail: CT & MAView Trail Details

    4 Reviews

    North Adams, MA

    • Hiking  
    •  138 miles
    •  Guide

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

  • Metacomet-Monadnock Trail, Holyoke RangeView Trail Details

    4 Reviews

    South Hadley, MA

    • Hiking  
    •  9 miles
    •  Guide

    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 ...

  • Chester-Blandford State ForestView Trail Details

    4 Reviews

    Chester, MA

    •  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 River at Agawam. ...

  • October Mountain State ForestView Trail Details

    4 Reviews

    Lee, MA

    •  3.5 hours
    •  6.7 miles
    •  Guide

    This hike follows the long-distance Appalachian Trail over Becket (2,200 feet) and Walling (2,220 feet) Mountains, then drops down to the shore ...

  • Mount GreylockView Trail Details

    4 Reviews

    Adams, MA

    • Hiking  
    •  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 peak in Massachusetts ...

  • Mount Toby State ReservationView Trail Details

    4 Reviews

    Amherst, MA

    • Hiking  
    •  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), this loop explores ...

  • Borderland State ParkView Trail Details

    4 Reviews

    Sharon, MA

    • Hiking  
    •  7.4 miles
    •  Guide

    Managed from the start for wildlife and nature appreciation, the 1906 estate of botanist Oakes Ames and his artist wife, Blanche, offers present-day ...

  • Blue HillsView Trail Details

    3 Reviews

    Milton, MA

    • Mountain Biking  
    •  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 trail system and varied ...

  • World's End ReservationView Trail Details

    3 Reviews

    Hingham, MA

    • Walking  
    •  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 one natural area, I ...

  • Cape Ann CruiseView Trail Details

    3 Reviews

    Gloucester, MA

    • Road Biking  
    •  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 cottages and grand ...

  • Lowell-Dracut-Tyngsboro State ParkView Trail Details

    3 Reviews

    Lowell, MA

    • Mountain Biking  
    •  15 miles
    •  Guide

    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 ...

  • Chebacco WoodsView Trail Details

    3 Reviews

    Hamilton, MA

    • Mountain Biking  
    •  1 hour
    •  4.8 miles
    •  Guide

    The solitude and stillness found here is remarkably similar to that found in the wilderness areas of Maine, New Hampshire, and Vermont. Though ...

  • Norwottuck Rail-TrailView Trail Details

    3 Reviews

    Northampton, MA

    •  8.5 miles
    •  Guide

    Historians believe that the Native Americans who first lived in the region named the area “Norwottuck,” meaning “in the midst of the river.”The ...

  • Ashuwillticook Rail TrailView Trail Details

    3 Reviews

    Lanesborough, MA

    • Mountain Biking  
    •  1.5 to 3 hours
    •  21.2 miles
    •  Guide

    Highlights: No technical obstacles! No hills! No following directions! Views of Mt. Greylock and wildflowers are grand, and provide a different ...

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