Best trails in Chestnut Hill

295 Reviews
Looking for a great trail near Chestnut Hill, Massachusetts? AllTrails has 6 great hiking trails, walking trails, forest 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 5 easy trails in Chestnut Hill ranging from 1.6 to 4.4 miles and from 111 to 259 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 Chestnut Hill
Top trails (6)
#1 - Chestnut Hill Reservoir Trail
Chestnut Hill, Massachusetts
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(81)
Length: 1.6 mi • Est. 40 m
1.5 loop around Chestnut Hill Reservoir. Nice views of Boston College and of Boston skylineShow more
#2 - Hammond Pond Reservation
Webster Conservation Area
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(115)
Length: 1.6 mi • Est. 43 m
Hammond Pond Reservation is a 1.6 mile moderately trafficked loop trail located near Chestnut Hill, Massachusetts that features a lake and is rated as moderate. The trail offers a number of activity oShow more
#3 - Lost Pond Trail
Lost Pond Conservation Area
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(34)
Length: 2.1 mi • Est. 58 m
Lost Pond Trail is a 2.1 mile moderately trafficked loop trail located near Chestnut Hill, Massachusetts that features beautiful wild flowers and is good for all skill levels. The trail offers a numbeShow more
#4 - Allandale Woods Trail
Allendale Glen Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(31)
Length: 2 mi • Est. 56 m
Allandale Woods Trail is a 2 mile moderately trafficked loop trail located near Chestnut Hill, Massachusetts that features a lake. The trail is good for all skill levels and is primarily used for hikShow more
#5 - Lost Pond Conservation Area
Chestnut Hill, Massachusetts
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(15)
Length: 4.4 mi • Est. 1 h 58 m
Lost Pond Conservation Trail Lost Pond Conservation TrailShow more
#6 - Hammond Pond Loop
Webster Conservation Area
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(19)
Length: 2.6 mi • Est. 1 h 10 m
Hammond Pond Loop is a 2.6 mile moderately trafficked loop trail located near Chestnut Hill, Massachusetts that features a lake and is good for all skill levels. The trail is primarily used for hikingShow more