Best trails in Massachusetts

87274 Reviews
Trying to find the best Massachusetts trails? AllTrails has 1,844 great hiking trails, 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 Sudbury, Milton or Plymouth, 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 1,188 easy trails in Massachusetts ranging from 0.6 to 34.4 miles and from -6 to 2,795 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 (1844)
#1 - Great Blue Hill via Skyline Trail
Blue Hills Reservation
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(1099)
Length: 3 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 tShow 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(510)
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 uShow more
#3 - Blue Hills Skyline Trail
Blue Hills Reservation
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(667)
Length: 7.5 mi • Est. 4 h 10 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 onShow more
#4 - Mount Watatic and Nutting Hill via Wapack Trail
Watatic Mountain State Wildlife Area
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(652)
Length: 2.8 mi • Est. 1 h 36 m
Mount Watatic and Nutting Hill via Wapack Trail is a 2.8 mile heavily trafficked loop trail located near Ashburnham, Massachusetts that features beautiful wild flowers and is rated as moderate. The trShow more
#5 - Skyline Trail Loop
Middlesex Fells Reservation
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(787)
Length: 7.6 mi • Est. 3 h 41 m
Skyline Trail Loop is a 7.6 mile heavily trafficked loop trail located near Medford, Massachusetts that features a lake and is rated as moderate. The trail offers a number of activity options and is bShow more
#6 - Charley's Loop Trail
Purgatory Chasm State Reservation
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(448)
Length: 1.7 mi • Est. 48 m
As of April 15, 2019, the Chasm Trail is closed due to slippery snow and ice conditions until further notice. Please refer to the park page for updates. A unique natural landmark, Purgatory Chasm ruShow more
#7 - Race Brook Falls and Mount Everett
Mount Everett State Reservation
hardYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(264)
Length: 6.1 mi • Est. 3 h 58 m
Race Brook Falls and Mount Everett is a 6.1 mile heavily trafficked out and back trail located near Sheffield, Massachusetts that features a waterfall and is only recommended for very experienced adveShow more
#8 - Mount Frissell and Brace Mountain Loop Trail
Mount Washington State Forest
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(255)
Length: 5 mi • Est. 2 h 44 m
A nice afternoon hike hitting all the main attractions on the western side of the Taconic Highlands. Show more
#9 - Mount Norwottuck
Mount Holyoke Range State Park
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(444)
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 VShow more
#10 - Lynn Woods Reservation
Lynn Woods Reservation
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(489)
Length: 4.4 mi • Est. 1 h 59 m
Lynn Woods Reservation is a 4.4 mile heavily trafficked loop trail located near Lynn, Massachusetts that features a lake and is rated as moderate. The trail offers a number of activity options and is Show more
Showing results 1 - 10 of 1844