Best Walking in Massachusetts

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

Learn more about Top Trails

#1. 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

#2. 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 all (About Top Trails)
Published by The Globe Pequot Press

#3. Norwottuck Rail-Trail


Historians believe that the Native Americans who first lived in the region named the area “Norwottuck,” meaning “in the midst of the river.”The rail line originated as a Massachusetts Central Railroad…
From the guidebook "Rails To Trails: Connecticut, Rhode Island, Massachusetts, Vermont, New Hampshire, Maine"
Northampton, MA - Cross-Country Skiing, Rail-Trails, Road Biking, Walking - 8.5 miles
Published by The Globe Pequot Press

#4. Falmouth Shining Sea Path


Enjoy the brilliant views of the Nantucket and Vineyard Sounds on this short trail connecting Falmouth and Woods Hole. Surface: Asphalt. Location: Barnstable County.…
From the guidebook "Rails To Trails: Connecticut, Rhode Island, Massachusetts, Vermont, New Hampshire, Maine"
Falmouth, MA - Cross-Country Skiing, Rail-Trails, Road Biking, Walking - 4 miles
Published by The Globe Pequot Press

#5. Weir Hill Reservation


Weir Hill Reservation combines the best of woodlands, fields, and water. A hiker gets treated to views not only from the hilltop but also from the shores of beautiful Lake Cochichewick, a water-supply…
From the guidebook "Nature Walks in Eastern Massachusetts"
North Andover, MA - Walking - 3 miles
Published by Appalachian Mountain Club Books

#6. Wachusett Reservoir


Wachusett Reservoir was created in 1895 to solve the water needs of the greater Boston area. Today, the reservoir still supplies water to Boston (with the help of Quabbin Reservoir), but it also serve…
From the guidebook "Nature Walks in Eastern Massachusetts"
Boylston, MA - Walking
Published by Appalachian Mountain Club Books

#7. Lexington, Lincoln, and Concord along the Minute Man Trail


The battles of Lexington and Concord began the American Revolution. See where much of the action happened, visit restored colonial-era buildings, cross boardwalks over marshy wildlife sanctuaries, all…
From the guidebook "Walking Boston"
Lexington, MA - Walking - 5 miles
Published by Falcon Guides

#8. Along the Charles River: Boston - Cambridge


The Charles River is beautiful, historic, conveniently located, and great people-watching territory. Sunsets over the river from Boston are often beautiful. Early mornings are special, too. Sail or…
From the guidebook "Walking Boston"
Boston, MA - Walking - 3.75 miles
Published by Falcon Guides

#9. Moose Hill Wildlife Sanctuary


Have you ever longed to find some secluded hilltop and just sit peacefully, letting the breeze and quietness lull your senses? I have, and Moose Hill Wildlife Sanctuary in Sharon has one of the best v…
From the guidebook "Nature Walks in Eastern Massachusetts"
Sharon, MA - Walking - 4.25 miles
Published by Appalachian Mountain Club Books

#10. Southwest Corridor Park, Boston


The southwest corridor park was almost a highway. On this walk you can see what happened when the expressway plan was dropped, the narrow corridor became transit lines, and a park was built around it.…
From the guidebook "Walk Boston"
Boston, MA - Walking - 4.5 miles
Published by Appalachian Mountain Club Books

#11. Upper Charles River Reservation, Boston


A natural and wild quality pervades the Charles River’s banks upriver from the dam at Watertown Square. Unlike the riverbanks along the Charles River Basin—the well-known Boston and Cambridge Esplanad…
From the guidebook "Walk Boston"
Newton, MA - Walking - 6 miles
Published by Appalachian Mountain Club Books

#12. Hull Peninsula, Boston


One of Boston's best-kept secrets is the pleasure of walking the Hull peninsula—a long stretch of shoreline and flat, sandy public beach that welcomes discovery. The town’s relative isolation has cont…
From the guidebook "Walk Boston"
Hull, MA - Walking - 6.5 miles
Published by Appalachian Mountain Club Books

#13. 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

#14. Eliza Little Walking Trail


A pastoral walk across old farmland from a seventeenth-century farmhouse to the Merrimack estuary. The Eliza Little Walking Trail is part of the 170-mile Bay Circuit Walking Trail, which makes a half…
From the guidebook "Nature Walks along the Seacoast: Massachusetts, New Hampshire, & Maine"
Newbury , MA - Walking - 1 mile
Published by Appalachian Mountain Club Books

#15. Arlington, outside Boston


At first glance Arlington seems to be one more pleasant suburb of Boston—a good place to live without much for visitors to see. Not so. The town played a pivotal role in the American Revolution, as th…
From the guidebook "Walk Boston"
Arlington, MA - Walking - 5 miles
Published by Appalachian Mountain Club Books

#16. Southwest Corridor


This urban rail-trail takes you from downtown Boston to Jamaica Plain. It is used by bicyclists commuting to and from downtown and by outdoor enthusiasts looking for some fun in the sun near Boston.…
From the guidebook "Rails To Trails: Connecticut, Rhode Island, Massachusetts, Vermont, New Hampshire, Maine"
Boston, MA - Rail-Trails, Road Biking, Walking - 5 miles
Published by The Globe Pequot Press

#17. Deer Island, Boston


From a high hill on Deer Island, dramatic views spread out across Boston Harbor. You can see Boston’s sparkling skyline, lighthouses near and far, the harbor’s twenty-nine other islands, a new windmil…
From the guidebook "Walk Boston"
Boston, MA - Walking - 2.6 miles
Published by Appalachian Mountain Club Books

#18. Neponset River and Ashmont Hill, Boston


A quiet river flows through a widening estuary to Boston Harbor, past riverfront communities and a public beach. This river—the Neponset—is a little-known sister of the larger Charles River. The two r…
From the guidebook "Walk Boston"
Boston, MA - Walking - 2 miles
Published by Appalachian Mountain Club Books

#19. Downtown and Back Bay, Boston Marathon


This walk takes you to the several historic finish lines of the Boston Marathon and by marathon memorabilia and monuments through the lovely streets of Back Bay. Start at Eliot Hotel on Massachusett…
From the guidebook "Walking Boston"
Boston, MA - Walking - 0.8 mile
Published by Falcon Guides

#20. Boston Charlestown


Charlestown is Boston’s oldest neighborhood—and over the years has been arguably its most volatile. This single square mile of turf bred and witnessed conflicts almost from the arrival of European set…
From the guidebook "Walk Boston"
Charlestown, MA - Walking - 3.5 miles
Published by Appalachian Mountain Club Books