Best trails in Boston

870 Reviews
Looking for a great trail near Boston, Massachusetts? AllTrails has 20 great hiking trails, running trails, walking 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 Whitehall State Park or Great Brook Farm State Park, we've got you covered. You'll also find some great local park options, like Blue Hills Reservation or Middlesex Fells Reservation. Just looking to take a quick stroll? We've got 18 easy trails in Boston ranging from 0.6 to 10 miles and from 0 to 177 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 Boston
Top trails (20)
#1 - Boston's Freedom Trail
Boston Common
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(268)
Length: 7.6 mi • Est. 3 h 16 m
Users have reported this trail has a temporary closure due to COVID-19. Please see the park's website for up to date information. Discover the roots of the revolution and Boston's rich history on thiShow more
#2 - Boston Harbor and Castle Island
Marine Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(127)
Length: 2.2 mi • Est. 55 m
This is a great walk around a causeway to a historic fort that you won't want to miss This is a very beautiful area just south of Boston. You will walk around an enclosed bay past a beach, a WWII meShow more
#3 - Deer Island Trail
Boston Harbor Islands National Recreation Area
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(74)
Length: 2.7 mi • Est. 1 h 8 m
Deer Island Trail is a 2.7 mile heavily trafficked loop trail located near Boston, Massachusetts that features a great forest setting and is good for all skill levels. The trail is primarily used for Show more
#4 - Boston's Emerald Necklace Trail
Boston, Massachusetts
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(18)
Length: 32.5 mi • Est. Multi-day
Discover Frederick Law Olmsted's famous system of parks on this bicycle tour of the historic Emerald Necklace. From the shaded boulevard on Commonwealth Avenue to the popular shores of Jamaica Pond toShow more
#5 - Paul Revere Ride to Freedom Bike Tour
Boston, Massachusetts
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(5)
Length: 45.8 mi • Est. Multi-day
This guide takes you from the Old North Church in Boston's North End and follows Revere's ride on April 18, 1775. The Paul Revere Ride to Freedom takes you from the Old North Church in Boston's North Show more
#6 - Millenium Park
Cutler Park Reservation
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(51)
Length: 3.6 mi • Est. 1 h 33 m
Millenium Park is a 3.6 mile moderately trafficked loop trail located near Boston, Massachusetts that features a river and is good for all skill levels. The trail offers a number of activity options aShow more
#7 - Jamaica Pond and Victorian Jamaica Plain
Emerald Necklace
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(30)
Length: 3.2 mi • Est. 1 h 21 m
Jamaica Pond and Victorian Jamaica Plain is a 3.2 mile heavily trafficked loop trail located near Boston, Massachusetts that features a lake and is good for all skill levels. The trail offers a numberShow more
#8 - Public Garden Monument Walking Tour
Boston Public Gardens
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(39)
Length: 1.1 mi • Est. 27 m
Monuments, sculptures beckon in Boston Public GardenShow more
#9 - Neponset
Neponset River Reservation
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(68)
Length: 3.2 mi • Est. 1 h 21 m
Neponset is a 3.2 mile moderately trafficked out and back trail located near Boston, Massachusetts that features beautiful wild flowers and is good for all skill levels. The trail is primarily used foShow more
#10 - Jamaica Pond
Olmsted Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(51)
Length: 1.5 mi • Est. 38 m
Jamaica Pond is a 1.5 mile moderately trafficked loop trail located near Boston, Massachusetts that offers scenic views and is good for all skill levels. The trail offers a number of activity options Show more
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