Best trails in Chilmark

90 Reviews
Looking for a great trail near Chilmark, Massachusetts? AllTrails has 6 great views 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 Colt State Park or South Cape Beach State Park, we've got you covered. You'll also find some great local park options, like Weetamoo Woods or McBratney Land. Just looking to take a quick stroll? We've got 4 easy trails in Chilmark ranging from 1.1 to 3.7 miles and from 75 to 301 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 Chilmark
Top trails (6)
#1 - Menemsha Hills Reservation Trail
Chilmark, Massachusetts
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(43)
Length: 3.7 mi • Est. 1 h 43 m
Menemsha Hills Reservation Trail is a 3.7 mile moderately trafficked loop trail located near Chilmark, Massachusetts that offers the chance to see wildlife and is good for all skill levels. The trail Show more
#2 - Waskosim's Rock Reservation (Chilmark)
Chilmark, Massachusetts
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(22)
Length: 2.5 mi • Est. 1 h 7 m
Waskosim's Rock Reservation (Chilmark) is a 2.5 mile moderately trafficked loop trail located near Chilmark, Massachusetts that features beautiful wild flowers and is rated as moderate. The trail offeShow more
#3 - Tiasquam Valley to Wiskosim’s Rock
Francis Newhall Woods Preserve
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(7)
Length: 3.7 mi • Est. 1 h 46 m
Tiasquam Valley to Wiskosim’s Rock is a 3.7 mile lightly trafficked out and back trail located near Chilmark, Massachusetts that offers scenic views and is rated as moderate. The trail is primarily usShow more
#4 - Peaked Hill Loop
Chilmark, Massachusetts
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(8)
Length: 1.7 mi • Est. 47 m
Peaked Hill Loop is a 1.7 mile lightly trafficked loop trail located near Chilmark, Massachusetts that offers the chance to see wildlife and is good for all skill levels. The trail is primarily used Show more
#5 - Moshup Beach Trail
Chilmark, Massachusetts
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarGray Star(3)
Length: 0.4 mi • Est. 11 m
Moshup Beach Trail is a 0.4 mile heavily trafficked out and back trail located near Chilmark, Massachusetts that offers the chance to see wildlife and is good for all skill levels. The trail is primarShow more
#6 - Raft and Marl Ponds Loop
Chilmark, Massachusetts
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(7)
Length: 1.1 mi • Est. 32 m
Raft and Marl Ponds Loop is a 1.1 mile loop trail located near Chilmark, Massachusetts that features a lake and is good for all skill levels. The trail is primarily used for hiking and nature trips.Show more