Best trails in Massachusetts

160,480 Reviews
Trying to find the best Massachusetts trails? AllTrails has 2,200 great hiking trails, trail running trails, mountain biking trails and more, with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers, and nature lovers like you. If you're looking for the best trails around Plymouth, Sudbury or Milton, we've got you covered. If you're looking for great Massachusetts state park trails, check out Mount Holyoke Range State Park. Or for some great local park options, check out Lynn Woods Reservation near Lynn or Boston Common near Boston. Just looking to take a quick stroll? We've got 1,446 easy trails in Massachusetts ranging from 0.6 to 34.4 miles and from -6 to 2,575 feet above sea level. Start checking them out and you'll be out on the trail in no time!
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Map of trails in Massachusetts
Top trails (2200)
#1 - Great Blue Hill via Skyline Trail
Blue Hills Reservation
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(1995)
Length: 3.0 mi • Est. 1 h 13 m
This relatively short hike in the forests of the Blue Hills Reservation has some great views of the Boston skyline. Eliot Tower is a fantastic lookout point to see the entire Boston region. Although the trail is not too technical, trekking poles can help you keep your footing in tricky areas.Show more
#2 - Mount Greylock via Bellows Pipe and Thunderbolt Trail
Mount Greylock State Reservation
hardYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(960)
Length: 5.1 mi • Est. 3 h 34 m
The trail starts from parking area up to AT via Old Summit Road. A little confusing with the skiing signs, but head east up to AT. Hike along AT to a point where Thunderbolt ties in, and make a push up to the summit of Greylock. Take the thunderbolt trail north until you reach the Appalachian trail (marked while), where you will turn left until you reach the Mount Greylock summit. The Thunderbolt Trail was originally a CCC built ski trail, and in 1936 hosted the United States Eastern Alpine Ski Championships. Its current course has been somewhat altered from the original, but is no less challenging. The Thunderbolt Foot Trail climbs gently west winding through the forest south of Hoxie Brook, and eventually the foot trail will intersect the old ski trail on your right. At about the half mile mark, the trail becomes considerably steeper and heads northwesterly towards the summit ridge. This stretch is quite broad and is recognizable as a steep, tree-lined ski run. At about the 1.5 mile mark the trail reaches the summit ridge, where you have a beautiful view upon the town of Adams from Hadley Lookout.Show more
#3 - Mount Watatic and Nutting Hill via Wapack Trail
Watatic Mountain State Wildlife Area
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(1162)
Length: 2.8 mi • Est. 1 h 36 m
#4 - Skyline Trail Loop
Middlesex Fells Reservation
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(1246)
Length: 8.4 mi • Est. 3 h 22 m
This route uses several different trails to create a loop. There are many intersecting trails that can be confusing so we recommend recording your activity to avoid going off route.Show more
#5 - Blue Hills Skyline Trail
Blue Hills Reservation
hardYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(865)
Length: 15.1 mi • Est. 8 h 4 m
NOTE: The route on this page has the hiker starting at the eastern terminus on Willard Street and going west. Hikers can also start from the western terminus. This alternate route can also be found on AllTrails. Blue Hills Reservation is a popular hiking and mountain biking destination located about 10 miles south of downtown Boston. The Massachusetts State Park offers more than 125 miles of trails and is one of the largest parcels of undeveloped conservation land within the Boston metropolitan area. The park offers spectacular views and is a great place to see fall foliage. Visitors interested in the reservation's ecology will enjoy the numerous swamps, ponds, marshes and meadows, as well as a number of endangered species. The Blue Hills Skyline Trail features varied terrain and fantastic views of Eliot Tower and the Boston Skyline. The hiking trail summits a number of hills including Hancock Hill, Hemingway Hill, Wolcott Hill and Great Blue Hill at an altitude of 635 feet - the highest point in the reservation. The trailhead can be accessed from the Willard Street parking area. Horseback riding, trail running and cross-country skiing are also popular activities. Visitors interested in purchasing a reservation map for the best trails in the park can do so at the Reservation Headquarters office.Show more
#6 - Mount Norwottuck
Mount Holyoke Range State Park
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(802)
Length: 3.4 mi • Est. 1 h 48 m
Highest peak in the Holyoke range, has commanding views of the entire pioneer valley. The loop for Mt. Norwottuck combines the Robert Frost trail (orange) and the M&M trail (white). Start from the Visitor's Center on the combined Robert Frost trail and M&M Trail (orange & white). Stay left on the Robert Frost (orange) when the M&M splits off. Eventually you will reconnect with the M&M, and there you will stay right on go onto the M&M Trail (white). You will then begin an ascent to the summit through ledges. From the summit continue to follow the M&M trail (white) down and eventually you will rejoin the Robert Frost trail (orange) where you split off on the way up. Stay left on the combined Robert Frost (orange) and M&M trail (white) to get back to the visitor center.Show more
#7 - Hickey and Peeskawso Peak Trail
Monument Mountain Reservation
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(636)
Length: 2.8 mi • Est. 1 h 35 m
Note: The term squaw is considered universally offensive by Indigenous groups in America due to its use for hundreds of years in a derogatory context. Indigenous activists have continued to work both locally and in more general educational efforts, to rename the locations across North America that contain the slur, as well as to eliminate the slur from the lexicon in general. See here for more info: https://en.wikipedia.org/wiki/Squaw#Efforts_to_rename_placenames_and_terms_with_squaw_in_themShow more
#8 - Race Brook Falls and Mount Everett
Mount Everett State Reservation
hardYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(401)
Length: 6.1 mi • Est. 3 h 58 m
#9 - Blue Hills Skyline Loop
Blue Hills Reservation
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(767)
Length: 5.4 mi • Est. 2 h 38 m
#10 - Bash Bish Falls Trail
Bash Bish Falls State Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(478)
Length: 2.1 mi • Est. 1 h 12 m
Note: As of August 2020, the Massachusetts side of parking is closed. Bash Bish Falls is a great short hiking trail to the highest waterfall in the state of Massachusetts. The falls are located in Southwestern Massachusetts in the Taconic Mountains of Berkshire County, which neighbors Mount Washington State Forest in Massachusetts and Taconic State Park in New York. The park is maintained by the Massachusetts Department of Conservation and Recreation. There are a few access points to the falls and more than one parking lot. You can choose to start from the New York side and cross the state line into Massachusetts or start at either of the two Massachusetts trailheads. Starting at the lower parking area off of Falls Road, this short hike follows a rugged trail along Bash Bish brook through mature forest and over boulders, tree roots, natural stone stairs, and long wooden steps. You are soon rewarded with a view of the beautiful waterfall. The twin falls cascade into a serene pool. Swimming is not allowed in the pool. Use caution as the stones down around the falls are smooth and slick from years of traffic and it is easy to slip.Show more
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