Best Horseback Riding in Massachusetts

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

  • #1 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 ...

  • #2 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 ...

  • #3 Upton State Forest

    2 Reviews

    Upton, MA

    Well-marked dirt trails lead you past lady’s slipper flowers and lichen-crusted boulders to Dean Pond, a great place to stop for lunch. Return to your car on the Mammoth Rock Trail, scrambling ...
    •  2 hours
    •  4.3 miles
    •  Guide

    Well-marked dirt trails lead you past lady’s slipper flowers and lichen-crusted boulders to Dean Pond, a great place to ...

  • #4 Mount Pisgah Conservation Area

    2 Reviews

    Northborough, MA

    Mount Pisgah is 715 feet above sea level, but is scarcely elevated at all from the trailhead. This flat hike winds through mature white pine and red oak trees and a grid of stone walls, then ...
    •  1-1.5 hours
    •  2.6 miles
    •  Guide

    Mount Pisgah is 715 feet above sea level, but is scarcely elevated at all from the trailhead. This flat hike winds through ...

  • #5 Blue Hills Reservation

    2 Reviews

    Milton, MA

    Start at a sea-level pond and bog and, in just 0.5 mile, climb nearly 500 feet to Tucker Hill, passing through three separate ecosystems. Follow the high ridge along the much-loved Skyline ...
    •  2.5 to 3 hours
    •  3.8 miles
    •  Guide

    Start at a sea-level pond and bog and, in just 0.5 mile, climb nearly 500 feet to Tucker Hill, passing through three separate ...

  • #6 Boxford State Forest

    1 Reviews

    Boxford, MA

    This walk through the woods doesn’t offer steep climbs or expansive views, but for its proximity to civilization, Boxford State Forest offers quiet trails and glassy ponds, with signs of beaver, ...
    •  About 2 hours
    •  5.2 miles
    •  Guide

    This walk through the woods doesn’t offer steep climbs or expansive views, but for its proximity to civilization, Boxford ...

  • #7 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 ...

  • #8 Maudslay State Park

    2 Reviews

    Newburyport, MA

    This flat loop around a 480-acre park begins with a visit to the ruins of a historic mansion, with commanding views of the Merrimack River and stunning summer flower blooms. The path then traces ...
    •  1.5-2 hours
    •  3.9 miles
    •  Guide

    This flat loop around a 480-acre park begins with a visit to the ruins of a historic mansion, with commanding views of the ...

  • #9 Great Brook Farm State Park

    1 Reviews

    Carlisle, MA

    Located in the town of Carlisle, about 12 miles north of Concord, 25 miles northwest of Boston. The terrain is relatively flat, with small hills. Some of the single-track trails have short, steep ...
    •  8 miles
    •  Guide

    Located in the town of Carlisle, about 12 miles north of Concord, 25 miles northwest of Boston. The terrain is relatively ...

  • #10 Borderland State Park

    2 Reviews

    Sharon, MA

    This wet, sandy land is a typical southeastern Massachusetts ecosystem, with the acidic soil beloved by cranberry bogs and cedar swamps. The park’s many ponds were formed by damming its streams, ...
    •  2.5 to 3 hours
    •  4 miles
    •  Guide

    This wet, sandy land is a typical southeastern Massachusetts ecosystem, with the acidic soil beloved by cranberry bogs and ...

  • #11 Douglas State Forest

    1 Reviews

    Webster, MA

    This 4,640-acre forest sits at the corner of Massachusetts, Connecticut, and Rhode Island. Far from being just a flat, sandy floodplain, the land includes the cedar swamp and basin marsh ...
    •  2 hours
    •  3.8 miles
    •  Guide

    This 4,640-acre forest sits at the corner of Massachusetts, Connecticut, and Rhode Island. Far from being just a flat, ...

  • #12 Freetown/Fall River State Forest

    1 Reviews

    Fall River, MA

    This sprawling, flat, sandy park is a typical Massachusetts coastal forest, filled with deer, pheasants, and freshwater fish, and surrounded by nearby cranberry farms. The hike offers a tour ...
    •  About 2.5 hours
    •  5.6 miles
    •  Guide

    This sprawling, flat, sandy park is a typical Massachusetts coastal forest, filled with deer, pheasants, and freshwater ...

  • #13 Massasoit State Park

    1 Reviews

    Middleboro, MA

    Located on the northern edge of Massachusetts’s coastal sand plain, this park marks a transition from the more thickly forested hills of northeastern Massachusetts to the flat, sandy lands of ...
    •  2 hours
    •  3.4 miles
    •  Guide

    Located on the northern edge of Massachusetts’s coastal sand plain, this park marks a transition from the more thickly forested ...

  • #14 Noanet Woodlands Reservation

    1 Reviews

    Dover, MA

    Like the nearby, affluent town of Dover, this rolling ramble seems built for comfort. Its broad, well-marked trails with their numbered intersections bring you across a brook and over a scenic ...
    •  2 hours
    •  3.2 miles
    •  Guide

    Like the nearby, affluent town of Dover, this rolling ramble seems built for comfort. Its broad, well-marked trails with ...

  • #15 Bald Hill Road

    5 Reviews

    J. C. Phillips Sanctuary, MA

    Bald Hill Road is a hiking, biking, and horse trail in Boxford, Massachusetts. It is within J. C. Phillips Sanctuary (Lockwood) and J. C. Phillips Sanctuary. It is 1.3 miles long and begins at ...
    •  1.3 miles

    Bald Hill Road is a hiking, biking, and horse trail in Boxford, Massachusetts. It is within J. C. Phillips Sanctuary (Lockwood) ...

  • #16 Bradley Palmer State Park

    0 Reviews

    Topsfield, MA

    This loop follows the Ipswich River as it cuts between Bradley Palmer State Park and the adjacent Willowdale State Forest. Together they offer 721 acres and over 20 miles of trails. For a small ...
    •  1.5-2 hours
    •  2.5 miles
    •  Guide

    This loop follows the Ipswich River as it cuts between Bradley Palmer State Park and the adjacent Willowdale State Forest. ...

  • #17 Ward Reservation

    0 Reviews

    Andover, MA

    The reservation is split evenly by the Andover and North Andover town line, with drumlins on either side: Holt Hill in Andover and Boston and Shrub Hills in North Andover. The Cat Swamp lies ...
    •  2 hours
    •  4 miles
    •  Guide

    The reservation is split evenly by the Andover and North Andover town line, with drumlins on either side: Holt Hill in ...

  • #18 Harold Parker Road

    4 Reviews

    Essex County, MA

    Harold Parker Road is a hiking, biking, and horse trail in Essex County, Massachusetts. It is 1.3 miles long and begins at 119 feet altitude. Traveling the entire trail is 2.6 miles with a total ...
    •  1.3 miles

    Harold Parker Road is a hiking, biking, and horse trail in Essex County, Massachusetts. It is 1.3 miles long and begins at ...

  • #19 Eliza Little Trail

    1 Reviews

    Essex County, MA

    Eliza Little Trail is a hiking, biking, and horse trail in Essex County, Massachusetts. It is 0.4 miles long and begins at 11 feet altitude. Traveling the entire trail is 0.8 miles with a total ...
    •  0.4 miles

    Eliza Little Trail is a hiking, biking, and horse trail in Essex County, Massachusetts. It is 0.4 miles long and begins ...

  • #20 Destruction Brook Woods Preserve

    1 Reviews

    Dartmouth, MA

    Located near historic Russell Mills in Dartmouth, this preserve once contained an active farmstead and millworks. Although enveloped in the deep woods, remnants of long-ago human habitation are ...
    •  2.5 hours
    •  3.7 miles
    •  Guide

    Located near historic Russell Mills in Dartmouth, this preserve once contained an active farmstead and millworks. Although ...