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Best trails in Milton

5,175 Reviews
Looking for a great trail near Milton, Massachusetts? AllTrails has 32 great hiking trails, trail 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 Borderland State Park or Whitehall State Park, we've got you covered. You'll also find some great local park options, like Blue Hills Reservation or Middlesex Fells Reservation. Ready for some activity? There are 19 moderate trails in Milton ranging from 1.4 to 6 miles and from 101 to 626 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 Milton
Top trails (32)
#1 - Great Blue Hill via Skyline Trail
Blue Hills Reservation
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(1675)
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 the trail is not too technical, trekking poles can help you keep your footing in tricky areas.Show more
#2 - Buck Hill
Blue Hills Reservation
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(395)
Length: 2.9 mi • Est. 1 h 36 m
#3 - Great Blue Hill via Coon Hollow Path
Blue Hills Reservation
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(318)
Length: 1.5 mi • Est. 51 m
#4 - Skyline Loop
Blue Hills Reservation
hardYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(220)
Length: 10.3 mi • Est. 5 h 38 m
#5 - Hancock Hill and Hemenway Hill Loop
Blue Hills Reservation
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(189)
Length: 1.4 mi • Est. 47 m
#6 - Wolcott Hill Loop Trail
Blue Hills Reservation
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(201)
Length: 2.3 mi • Est. 1 h 14 m
The Wolcott Trail is quiet, easy, and gently sloped for a good portion of it and the Eliot Tower has great hill trails but can be very busy. The section of north skyline is fun but not easy! The level forest track back to the beginning is a welcome change of pace. Offline map is recommended to get oriented as several users have reported that this trail is not well marked.Show more
#7 - Houghton's Pond to Buck Hill
Blue Hills Reservation
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(162)
Length: 3.5 mi • Est. 1 h 47 m
#8 - Museum to Skyline Loop
Blue Hills Reservation
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(196)
Length: 4.4 mi • Est. 2 h 37 m
#9 - Houghton's Pond Recreation Area
Blue Hills Reservation
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(269)
Length: 1.1 mi • Est. 27 m
The Houghtons Pond Recreation Area offers a variety of recreational activities, including swimming, fishing, picnicking , and hiking as well as a playground, concession pavilion, and Visitors Center. Located only minutes from the bustle of downtown Boston, the DCR Blue Hills Reservation stretches over 7,000 acres from Quincy to Dedham, Milton to Randolph, providing a green oasis in an urban environment. With its scenic views, varied terrain and 125 miles of trails, the Blue Hills Reservation offers year-round enjoyment for the outdoor enthusiast.Show more
#10 - Buck Hill via Skyline Loop
Blue Hills Reservation
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(169)
Length: 2.6 mi • Est. 1 h 30 m
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