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Best Hiking in Massachusetts

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

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#1. 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 Publishing

#2. 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"
Boston , MA - Hiking - 4.5 miles    Best Trail in MA - Click to view all (About Top Trails)
Published by Falcon Publishing

#3. 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 Publishing

#4. 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

#5. 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

#6. 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

#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. 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    Best Trail in MA - Click to view all (About Top Trails)
Published by Falcon Publishing

#9. Bascom Lodge, Mount Greylock

  
A traditional lodge at the top of the highest summit in Massachusetts. A windblown summit looming in mists and tracked by the Appalachian Trail, yet visited by tourists who step out of their cars dres…
From the guidebook "Roughing It Easy in New England: Outdoor Adventures Near Lodgings"
North Adams , MA - Hiking Best Trail in MA - Click to view all (About Top Trails)
Published by Wilderness Press

#10. Appalachian Trail: Sages Ravine to Mount Everett to Jug End

  
Even the drive to the southern trailhead for this spectacular hike will be a delight, up high in the town of Mount Washington, smallest (by population) in the commonwealth. The adjacent Mount Washing…
From the guidebook "Exploring the Appalachian Trail: Hikes in Southern New England"
Mount Washington , MA - Hiking - 11.2 miles    Best Trail in MA - Click to view all (About Top Trails)
Published by Stackpole Books

#11. Appalachian Trail: Cheshire to Mount Greylock

  
The best place to begin climbing Mount Greylock is in your mind. Take a leap of the imagination, as Herman Melville did from his study at Arrowhead in Pittsfield, where he positioned his writing desk…
From the guidebook "Exploring the Appalachian Trail: Hikes in Southern New England"
Cheshire , MA - Hiking - 7.6 miles    Best Trail in MA - Click to view all (About Top Trails)
Published by Stackpole Books

#12. 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 Publishing

#13. Blue Hills Reservation

  
Start at a sea level pond and bog, and in just one half mile, climb nearly 500 feet to Tucker Hill, passing through three separate ecosystems. Follow the high ridge along the much-loved Skyline Trail…
From the guidebook "Hiking Massachusetts"
Randolph , MA - Hiking - 4.75 miles   
Published by Falcon Publishing

#14. 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-…
From the guidebook "Hiking Southern New England"
Amherst , MA - Hiking - 5.5 miles   
Published by Falcon Publishing

#15. 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 - Hiking - 4 miles   
Published by Falcon Publishing

#16. 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

#17. 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

#18. 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 Publishing

#19. Mount Pisgah, Northborough Conservation Lands

  
Mount Pisgah is 715 feet above sea level, but is scarcely elevated at all from the trailhead. This flat hike winds through mature trees and a grid of stone walls, then skirts a steep ridgeline, offeri…
From the guidebook "Hiking Massachusetts"
Northborough , MA - Hiking - 3 miles   
Published by Falcon Publishing

#20. Broadmoor Wildlife Sanctuary

  
Broadmoor is a sanctuary rich in both wildlife and history. Thomas Swain’s mill was built in the 1690s and was powered by the waters of Indian Brook and the holding pond, or millpond. Today you can se…
From the guidebook "Nature Walks in Eastern Massachusetts"
Natick , MA - Hiking - 3 miles   
Published by Appalachian Mountain Club Books

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