Trails.com offers a list of the best hiking in Massachusetts. These are there recommendations:
#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.
North Adams, MA – Hiking – 138 miles
(About Top Trails)
#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 station
#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
South Egremont, MA – Hiking – 15 miles
(About Top Trails)#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 (About Top Trails)
#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 Alande
Mount Washington, MA – Hiking – 5.6 miles
(About Top Trails)#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 definitely one of the nicest hikes
Sheffield, MA – Hiking – 5.4 miles
(About Top Trails)#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
Adams, MA – Hiking – 2.2 miles
(About Top Trails)#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 area
#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 dressed.
North Adams, MA – Hiking
(About Top Trails)
#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 Washington
From the guidebook “Exploring the Appalachian Trail: Hikes in Southern New England”
Mount Washington, MA – Hiking – 11.2 miles (About Top Trails)
#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 (About Top Trails)
#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.
South Hadley, MA – Hiking – 9 miles
(About Top Trails)#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
Randolph, MA – Hiking – 4.75 miles
#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
Amherst, MA – Hiking – 5.5 miles
#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 mature trees.
Princeton, MA – Hiking – 4 miles
#16. Gates Pond
Finding a lake left in its natural state is rare indeed here in eastern Massachusetts. Here is a pond that does not have a single cottage on its shoreline, and the trail that circles it is open for all
Berlin, MA – Hiking – 2.5 miles
#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.
Stockbridge, MA – Hiking – 1.4 miles
#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.
Northampton, MA – Hiking – 4.5 miles
#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, offering terrific views.
Northborough, MA – Hiking – 3 miles
#20. Broadmoor Wildlife Sanctuary
Broadmoor is a sanctuary rich in both wildlife and history. Thomas Swain mill was built in the 1690s and was powered by the waters of Indian Brook and the holding pond, or millpond.
Natick, MA – Hiking – 3 miles
