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.

Learn more about Top Trails

#1. Cape Cod Rail-Trail


Among the most scenic recreation trails in Massachusetts and a favorite with cyclists and day hikers, the Cape Cod Trail provides access to beaches, fresh water ponds, cranberry bogs and wild wetlands…
From the guidebook "Rails To Trails: Connecticut, Rhode Island, Massachusetts, Vermont, New Hampshire, Maine"
Harwich, MA - Birding, Cross-Country Skiing, Fishing, Horseback Riding, Mountain Biking, Rail-Trails, Road Biking, Trail Running - 26 miles Best Trail in ma - Click to view allBestBirding, Cross-Country Skiing, Fishing, Horseback Riding, Mountain Biking, Rail-Trails, Road Biking, Trail Running Trail - Click to view all (About Top Trails)
Published by The Globe Pequot Press

#2. Skinner State Park


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 traverse…
From the guidebook "Hiking Massachusetts"
Northampton, MA - Cross-Country Skiing, Hiking, Horseback Riding, Mountain Biking - 4.7 miles
Published by Falcon Guides

#3. Upton State Forest


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 bet…
From the guidebook "Hiking Massachusetts"
Upton, MA - Hiking, Horseback Riding, Mountain Biking - 4.3 miles
Published by Falcon Guides

#4. Mount Pisgah Conservation Area


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 skirts…
From the guidebook "Hiking Massachusetts"
Northborough, MA - Hiking, Horseback Riding, Mountain Biking - 2.6 miles
Published by Falcon Guides

#5. Blue Hills Reservation


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 Trail t…
From the guidebook "Hiking Massachusetts"
Milton, MA - Cross-Country Skiing, Hiking, Horseback Riding, Mountain Biking - 3.8 miles
Published by Falcon Guides

#6. Boxford State Forest


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, deer,…
From the guidebook "Hiking Massachusetts"
Boxford, MA - Birding, Cross-Country Skiing, Hiking, Horseback Riding - 5.2 miles
Published by Falcon Guides

#7. Marblehead Rail-Trail


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 this trai…
From the guidebook "Rails To Trails: Connecticut, Rhode Island, Massachusetts, Vermont, New Hampshire, Maine"
Marblehead, MA - Cross-Country Skiing, Horseback Riding, Rail-Trails, Road Biking, Walking - 5 miles
Published by The Globe Pequot Press

#8. Maudslay State Park


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 t…
From the guidebook "Hiking Massachusetts"
Newburyport, MA - Cross-Country Skiing, Hiking, Horseback Riding, Mountain Biking, Trail Running - 3.9 miles
Published by Falcon Guides

#9. Great Brook Farm State Park


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 asce…
From the guidebook "Mountain Biking Southern New England"
Carlisle, MA - Cross-Country Skiing, Horseback Riding, Mountain Biking - 8 miles
Published by Falcon Guides

#10. Borderland State Park


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, first…
From the guidebook "Hiking Massachusetts"
Sharon, MA - Cross-Country Skiing, Hiking, Horseback Riding, Mountain Biking, Trail Running - 4 miles
Published by Falcon Guides

#11. Douglas State Forest


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 ecosystem…
From the guidebook "Hiking Massachusetts"
Webster, MA - Cross-Country Skiing, Hiking, Horseback Riding, Mountain Biking - 3.8 miles
Published by Falcon Guides

#12. Freetown/Fall River State Forest


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 of th…
From the guidebook "Hiking Massachusetts"
Fall River, MA - Hiking, Horseback Riding, Mountain Biking - 5.6 miles
Published by Falcon Guides

#13. Midstate Trail Northbound - Day One


Cedar and hemlock trees fill this swampy, sandy land, which drains through many streams into nearby ponds and reservoirs. The trail follows wide, flat paths as it crosses MA 16 and ends at the village…
From the guidebook "Hiking Massachusetts"
Webster, MA - Cross-Country Skiing, Hiking, Horseback Riding, Mountain Biking - 7.8 miles
Published by Falcon Guides

#14. Noanet Woodlands Reservation


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 vista a…
From the guidebook "Hiking Massachusetts"
Dover, MA - Hiking, Horseback Riding, Mountain Biking, Trail Running - 3.2 miles
Published by Falcon Guides

#15. Massasoit State Park


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 Cape Co…
From the guidebook "Hiking Massachusetts"
Middleboro, MA - Cross-Country Skiing, Hiking, Horseback Riding, Mountain Biking - 3.4 miles
Published by Falcon Guides

#16. Bradley Palmer State Park


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 samp…
From the guidebook "Hiking Massachusetts"
Topsfield, MA - Birding, Cross-Country Skiing, Hiking, Horseback Riding, Mountain Biking, Snowshoeing - 2.5 miles
Published by Falcon Guides

#17. Midstate Trail Northbound - Day Two


Pass by corn fields, river basins, and a flood control dam on flat trails before switching to a section of paved roads and finishing at a tunnel crossing under US 20.…
From the guidebook "Hiking Massachusetts"
Webster, MA - Cross-Country Skiing, Hiking, Horseback Riding, Mountain Biking - 10.6 miles
Published by Falcon Guides

#18. Ward Reservation


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 betwe…
From the guidebook "Hiking Massachusetts"
Andover, MA - Cross-Country Skiing, Hiking, Horseback Riding - 4 miles
Published by Falcon Guides

#19. Noanet Woodlands


This 800-acre preserve offers a good mix of passive recreation like fishing in the mill pond for blue gills, summit views of the Boston skyline, and an historic ironwork site. This is all possible due…
From the guidebook "Best Hikes Near Boston"
Dover, MA - Birding, Fishing, Hiking, Horseback Riding, Mountain Biking, Snowshoeing - 2.6 miles
Published by Falcon Guides

#20. Rocky Narrows Preserve


Hike down the shores of the Charles River, starting at a canoe launch before climbing high within a short time up on a granite ridge above the narrows with 50-foottall rock walls on either side of the…
From the guidebook "Best Hikes Near Boston"
Sherborn, MA - Birding, Fishing, Hiking, Horseback Riding, Snowshoeing - 2.7 miles
Published by Falcon Guides