Best trails in Winchester, Massachusetts

844 Reviews
Looking for a great trail near Winchester, Massachusetts? AllTrails has 8 great hiking trails, lake 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 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 6 easy trails in Winchester ranging from 0.7 to 3.9 miles and from 16 to 275 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 Winchester, Massachusetts
Top trails (8)
#1 - Willow Spring Path and North Dam Road
Middlesex Fells Reservation
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(260)
Length: 2.3 mi • Est. 1 h 5 m
#2 - Middle and North Reservoir Loop
Middlesex Fells Reservation
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(176)
Length: 4.3 mi • Est. 1 h 43 m
#3 - Molly's Spring Road
Middlesex Fells Reservation
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(225)
Length: 0.7 mi • Est. 16 m
NOTE: Public access to this trail ends at the intersection of the Reservoir Trail. Please do not enter the reservoir area.Show more
#4 - Long Pond Loop via Cranberry Pond Path
Middlesex Fells Reservation
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(67)
Length: 1.3 mi • Est. 31 m
Note: Dogs are not allowed at the large reservoirs.Show more
#5 - Nanepashemet Road Loop
Middlesex Fells Reservation
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(43)
Length: 3.9 mi • Est. 1 h 34 m
#6 - Molly Springs Road to Reservoir Trail
Middlesex Fells Reservation
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(18)
Length: 2.6 mi • Est. 1 h 11 m
#7 - Mystic Lake Trail
Mystic Lakes State Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(25)
Length: 3.1 mi • Est. 1 h 17 m
#8 - Long Pond Nature Trail
Middlesex Fells Reservation
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(4)
Length: 1.6 mi • Est. 39 m
This is a short, two-mile nature trail in Middlesex Fells Reservation with educational stations describing the natural surroundings and forest ecosystems. It is marked by yellow blazes.Show more