Best Trail Running in Massachusetts

This list represents the most popular trail running in Massachusetts. Use this list to plan your next Massachusetts trail running 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. 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

#3. 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

#4. 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

#5. Rocky Woods Reservation


This loop tours three small lakes in a loop from Chickering Pond to Notch Pond to Echo Pond. As the path passes Whale Rock, it shows off the park’s low swamplands and their bog-loving trees, frogs, an…
From the guidebook "Hiking Massachusetts"
Medfield, MA - Cross-Country Skiing, Hiking, Mountain Biking, Trail Running - 1.9 miles
Published by Falcon Guides

#6. Monument Mountain


Monument Mountain attracts over 20,000 visitors per year and it is no wonder why, given the awe-inspiring 360-degree views of the Taconic Range, Mount Greylock, and the Housatonic River valley. Well-m…
From the guidebook "Best Easy Day Hikes: Berkshires"
Great Barrington, MA - Cross-Country Skiing, Hiking, Snowshoeing, Trail Running - 2.7 miles
Published by Falcon Guides

#7. Field Farm


Field Farm is a 316-acre property owned and maintained by The Trustees of Reservations. Field Farm encompasses 4 miles of hiking trails through a working hayfield and pasture, offering up some of the…
From the guidebook "Best Easy Day Hikes: Berkshires"
Adams, MA - Cross-Country Skiing, Hiking, Snowshoeing, Trail Running - 2.9 miles
Published by Falcon Guides

#8. Pond Loop: Beartown State Forest


The Berkshires are located in the far west section of Massachusetts, in the rolling hills between New York and Boston. Well known for their natural beauty and ease of access, the Berkshires have inspi…
From the guidebook "Best Easy Day Hikes: Berkshires"
Great Barrington, MA - Hiking, Snowshoeing, Trail Running - 1.8 miles
Published by Falcon Guides

#9. Ashuwillticook Rail Trail


The Ashuwillticook (ash-oo-will-ti-cook) Rail Trail is a former railroad corridor converted by the Massachusetts Department of Recreation and Conservation into a paved multiuse trail. This 10.9-mile p…
From the guidebook "Best Easy Day Hikes: Berkshires"
Lanesborough, MA - Cross-Country Skiing, Hiking, Rail-Trails, Road Biking, Trail Running - 10.9 miles
Published by Falcon Guides

#10. Burbank Trail


The Burbank Trail takes you through one of Berkshire Natural Resources Council’s premier properties. This 407-acre parcel is located on the southern slopes of Lenox Mountain. This hike will take you…
From the guidebook "Best Easy Day Hikes: Berkshires"
Stockbridge, MA - Cross-Country Skiing, Hiking, Mountain Biking, Snowshoeing, Trail Running - 3.2 miles
Published by Falcon Guides

#11. The Cascades


This short hike is just minutes from downtown North Adams and Williamstown. The Cascades, sometimes referred to as North Brook Falls, are a favorite cool-off spot for the locals, and one of the northe…
From the guidebook "Best Easy Day Hikes: Berkshires"
North Adams, MA - Hiking, Trail Running - 1.5 miles
Published by Falcon Guides

#12. Canoe Meadows Wildlife Sanctuary


Just minutes from downtown Pittsfield, Canoe Meadows offers a true wilderness feel. A very popular bird-watching spot in the Berkshires, hike along the Sackett Brook and view wildlife from the observa…
From the guidebook "Best Easy Day Hikes: Berkshires"
Pittsfield, MA - Cross-Country Skiing, Hiking, Snowshoeing, Trail Running - 1.8 miles
Published by Falcon Guides

#13. Old Mill Trail


This river walk mixes the natural beauty of the river with the rich history of a business that once thrived here in the Berkshires. This short walk takes you along the river’s edge, passing the ruins…
From the guidebook "Best Easy Day Hikes: Berkshires"
Pittsfield, MA - Hiking, Snowshoeing, Trail Running - 1.6 miles
Published by Falcon Guides

#14. Bartholomew’s Cobble


Hike through fields and forests on this nice route. Pass through beautiful fields of wildflowers on your way to Hurlburt’s Hill, a pristine scenic overlook. Stroll along the banks of the Housatonic Ri…
From the guidebook "Best Easy Day Hikes: Berkshires"
Great Barrington, MA - Cross-Country Skiing, Hiking, Snowshoeing, Trail Running - 3.8 miles
Published by Falcon Guides

#15. Back Bay Fens: Isabella’s Loop


What once was the mansion of Isabella Stewart, a wealthy Boston arts patron who at the turn of the twentieth century accumulated a massive collection of classical art from around the world, is now a m…
From the guidebook "Best Hikes Near Boston"
Boston, MA - Birding, Hiking, Trail Running - 1.7 miles
Published by Falcon Guides