Best Hiking in Massachusetts

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

Learn more about Top Trails

#1. Blue Hills Reservation


At this 7,000-acre open space south of Boston proper, some 100 miles of interlocking trails offer visitors a plethora of hike options. The skyline hills prove natural destinations and centerpieces for…
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. 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

#5. 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

#6. 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

#7. 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

#8. 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

#9. 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

#10. Jamaica Pond


An easy recreational trail offers a popular and pleasant circuit around historic Jamaica Pond.…
From the guidebook "AMC's Best Day Hikes Near Boston"
Brookline, MA - Hiking - 1.5 miles
Published by Appalachian Mountain Club Books

#11. Blackstone River and Canal Heritage


East of Massachusetts 122 in Uxbridge and Northbridge. Two hikes explore the park, traveling multiple-use trails: The Towpath Hike tours a scenic, mostly natural corridor through the old industrial b…
From the guidebook "Hiking Southern New England"
Uxbridge, MA - Hiking - 8 miles
Published by Falcon Guides

#12. Ice Glen


A short walk through a magnificent gorge of boulders, caves, ancient pines, and hemlocks. Though the Berkshires have been molded by geologic activity extending over hundreds of millions of years, some…
From the guidebook "Discover the Berkshires of Massachusetts"
Stockbridge, MA - Hiking - 1.4 miles
Published by Appalachian Mountain Club Books

#13. Mount Tom State Reservation - Dinosaur Footprints Reservation


West bank of the Connecticut River at Northampton. Three short hikes present the appeal of these two reservations. Special attractions: vistas, Triassic-period dinosaur footprints, floral fossils, Ey…
From the guidebook "Hiking Southern New England"
Northampton, MA - Hiking - 4.5 miles
Published by Falcon Guides

#14. Hancock Shaker Village Trail


Five miles west of Pittsfield. Constructed and maintained by the Boy Scouts of America, this circuit travels wooded, stream, and hilltop sites key to a 19th-cintury Shaker society. The tour visits a…
From the guidebook "Hiking Southern New England"
Pittsfield, MA - Hiking - 6.5 miles
Published by Falcon Guides

#15. Mount Watatic Trail


A not-too-tough climb to the top of Mount Watatic in Ashburnham will give kids the opportunity to do some safe summit exploring (there is no danger of them toppling off a cliff) while adults take in t…
From the guidebook "Best Hikes with Kids: Connecticut, Massachusetts, & Rhode Island"
Winchendon, MA - Hiking - 3 miles
Published by The Mountaineers Books

#16. Chester-Blandford State Forest


The Westfield River begins as three streams draining the eastern slope of the Berkshire Hills, and then flows into the Connecticut River at Agawam. State highways and railroads run parallel along its…
From the guidebook "Hiking Massachusetts"
Chester, MA - Hiking, Mountain Biking - 7.1 miles
Published by Falcon Guides

#17. Gates Pond


Finding a lake left in its natural state is rare indeed here in eastern Massachusetts. Here’s a pond that doesn’t have a single cottage on its shoreline, and the trail that circles it is open for all…
From the guidebook "Nature Walks in Eastern Massachusetts"
Berlin, MA - Hiking - 2.5 miles
Published by Appalachian Mountain Club Books

#18. Mount Grace State Forest


With a tall, eight-platform fire tower at its peak and the long-distance Metacomet- Monadnock (M-M) Trail running up its flank, Mount Grace deserves more attention than it gets. But located on the…
From the guidebook "Hiking Massachusetts"
Warwick, MA - Cross-Country Skiing, Hiking, Mountain Biking - 4.2 miles
Published by Falcon Guides

#19. 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

#20. Wachusett Mountain State Reservation


A ridgeline ascent to the highest point in Massachusetts east of the Berkshires, this hike is located on a state reservation with over 17 miles of trails. The loop passes through a succession of matur…
From the guidebook "Hiking Massachusetts"
Princeton, MA - Birding, Hiking - 3.9 miles
Published by Falcon Guides