Best Trails of Massachusetts

This list represents the most popular trails in Massachusetts (learn more about Top Trails). Use this list to plan your next Massachusetts outdoor trip. Select a state and/or activity below to find even more top trails.

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#1. Blue Hills Reservation


Ten miles south of downtown Boston. Three day hikes of varying length and difficulty explore key features of the Blue Hills chain. Special attractions: vistas, observation towers, historic weather st…
From the guidebook "Hiking Southern New England"
Milton, MA - Hiking - 4.5 miles Best Trail in MA - Click to view all (About Top Trails)
Published by Falcon Guides

#2. Lincoln Conservation Land (Mount Misery)


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…
From the guidebook "Nature Walks in Eastern Massachusetts"
Lincoln, MA - Hiking - 3 miles Best Trail in MA - Click to view all (About Top Trails)
Published by Appalachian Mountain Club Books

#3. Bash-Bish and Alander Mountains


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 Alander…
From the guidebook "Discover the Berkshires of Massachusetts"
Mount Washington, MA - Hiking - 5.6 miles Best Trail in MA - Click to view all (About Top Trails)
Published by Appalachian Mountain Club Books

#4. Duxbury Bay and Back River


Duxbury Bay is an extraordinarily lovely place to paddle. The bay and tidal rivers of the Great Salt Marsh offer exceptional natural beauty and serenity. Duxbury’s seven-mile-long barrier beach is a n…
From the guidebook "Sea Kayaking Coastal Massachusetts"
Duxbury, MA - Sea Kayaking - 11 miles Best Trail in MA - Click to view allBestSea Kayaking Trail - Click to view all (About Top Trails)
Published by Appalachian Mountain Club Books

#5. 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 allBestBirding, Cross-Country Skiing, Fishing, Horseback Riding, Mountain Biking, Rail-Trails, Road Biking, Trail Running Trail - Click to view allBestBirding, Cross-Country Skiing, Fishing, Horseback Riding, Mountain Biking, Rail-Trails, Road Biking, Trail Running Trail - Click to view allBestBirding, Cross-Country Skiing, Fishing, Horseback Riding, Mountain Biking, Rail-Trails, Road Biking, Trail Running Trail - Click to view allBestBirding, Cross-Country Skiing, Fishing, Horseback Riding, Mountain Biking, Rail-Trails, Road Biking, Trail Running Trail - Click to view allBestBirding, Cross-Country Skiing, Fishing, Horseback Riding, Mountain Biking, Rail-Trails, Road Biking, Trail Running Trail - Click to view allBestBirding, Cross-Country Skiing, Fishing, Horseback Riding, Mountain Biking, Rail-Trails, Road Biking, Trail Running Trail - 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

#6. Appalachian National Scenic Trail: CT & 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, fie…
From the guidebook "Hiking Southern New England"
North Adams, MA - Hiking - 138 miles Best Trail in MA - Click to view all (About Top Trails)
Published by Falcon Guides

#7. Mount Greylock


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 ahs…
From the guidebook "Discover the Berkshires of Massachusetts"
Adams, MA - Hiking - 2.2 miles Best Trail in MA - Click to view all (About Top Trails)
Published by Appalachian Mountain Club Books

#8. Alander Mountain Loop


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 overnight loop with side spurs travels the South Taconics,…
From the guidebook "Hiking Southern New England"
South Egremont, MA - Hiking - 15 miles Best Trail in MA - Click to view all (About Top Trails)
Published by Falcon Guides

#9. Race Brook Falls and Mount Everett


A daylong adventure to mountain cascades and up rocky windswept ridges to the very top of the southern Berkshires. This is not a particularly easy tramp, but it’s definitely one of the nicest hikes in…
From the guidebook "Discover the Berkshires of Massachusetts"
Sheffield, MA - Hiking - 5.4 miles Best Trail in MA - Click to view all (About Top Trails)
Published by Appalachian Mountain Club Books

#10. Metacomet-Monadnock Trail, Holyoke Range


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 summits,…
From the guidebook "Hiking Southern New England"
South Hadley, MA - Hiking - 9 miles Best Trail in MA - Click to view all (About Top Trails)
Published by Falcon Guides

#11. Mount Toby State Reservation


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 a 50-m…
From the guidebook "Hiking Southern New England"
Amherst, MA - Hiking - 5.5 miles Best Trail in MA - Click to view all (About Top Trails)
Published by Falcon Guides

#12. World's End Reservation


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 would recommend World’s End. In my opinion this is the mos…
From the guidebook "Nature Walks in Eastern Massachusetts"
Hingham, MA - Walking - 4.5 miles Best Trail in MA - Click to view allBestWalking Trail - Click to view all (About Top Trails)
Published by Appalachian Mountain Club Books

#13. Blue Hills


The Blue Hills Reservation is one of the premiere mountain biking areas in Eastern Massachusetts because of its extensive trail system and varied terrain. Bordered by six cities and towns, the reserva…
From the guidebook "Mountain Bike America: Boston"
Milton, MA - Mountain Biking - 3.8 miles Best Trail in MA - Click to view all (About Top Trails)
Published by The Globe Pequot Press

#14. Cape Cod Canal Striper Fishing


At just under 8 miles long, and averaging 600 feet wide, the Cape Cod Canal, which was planned to accommodate vessels drafting less than 30 feet, offers more productive striper spots for its area than…
From the guidebook "Striper Hot Spots"
East Falmouth, MA - Fishing Best Trail in MA - Click to view allBestFishing Trail - Click to view all (About Top Trails)
Published by Falcon Guides

#15. Minuteman Bikeway


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. Its historical significance is of particular note. The tr…
From the guidebook "Rails To Trails: Connecticut, Rhode Island, Massachusetts, Vermont, New Hampshire, Maine"
Arlington, MA - Mountain Biking, Rail-Trails, Road Biking, Walking - 11 miles Best Trail in MA - Click to view allBestMountain Biking, Rail-Trails, Road Biking, Walking Trail - Click to view allBestMountain Biking, Rail-Trails, Road Biking, Walking Trail - Click to view allBestMountain Biking, Rail-Trails, Road Biking, Walking Trail - Click to view allBestMountain Biking, Rail-Trails, Road Biking, Walking Trail - Click to view all (About Top Trails)
Published by The Globe Pequot Press

#16. Holyoke Range State Park


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, with regular, short, sometimes steep, climbs and descent…
From the guidebook "Mountain Biking Southern New England"
Amherst, MA - Mountain Biking - 10 miles Best Trail in MA - Click to view all (About Top Trails)
Published by Falcon Guides

#17. Wompatuck State Park


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 trail a chance to recover. You should expect numerous pud…
From the guidebook "Mountain Bike America: Boston"
Hingham, MA - Mountain Biking - 9.6 miles Best Trail in MA - Click to view all (About Top Trails)
Published by The Globe Pequot Press

#18. Connecticut River: Riverview Picnic Area to Barton Cove


The trip between Riverview Picnic Area and Barton Cove is an especially nice paddle, in part because the river changes moods, from wide and lazy to deep and narrow. Along the way you will pass between…
From the guidebook "Water Trails of Western Massachusetts"
Northfield, MA - Flatwater Kayaking & Canoeing - 5.3 miles Best Trail in MA - Click to view allBestFlatwater Kayaking & Canoeing Trail - Click to view all (About Top Trails)
Published by Appalachian Mountain Club Books

#19. Lowell-Dracut-Tyngsboro State Park


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 to the occasional horseback rider.…
From the guidebook "Mountain Biking Southern New England"
Lowell, MA - Mountain Biking - 15 miles Best Trail in MA - Click to view all (About Top Trails)
Published by Falcon Guides

#20. Savoy Mountain State Forest


From the guidebook "Best Tent Camping: New England"
Adams, MA - Campgrounds
Published by Menasha Ridge Press