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Best trails in Brewster

513 Reviews
Looking for a great trail near Brewster, Massachusetts? AllTrails has 13 great hiking trails, trail running 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 Nickerson State Park or Ellisville Harbor State Park, we've got you covered. You'll also find some great local park options, like Scusset Beach State Reservation or Trotting Park. Just looking to take a quick stroll? We've got 10 easy trails in Brewster ranging from 0.7 to 3.3 miles and from 16 to 137 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 Brewster
Top trails (13)
#1 - Cliff Pond Trail
Nickerson State Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(166)
Length: 2.7 mi • Est. 1 h 8 m
Cliff Pond Trail is a 2.7 mile moderately trafficked loop trail located near Brewster, Massachusetts that features beautiful wild flowers and is good for all skill levels. The trail offers a number ofShow more
#2 - Silas Road Trail
Nickerson State Park
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(70)
Length: 4.1 mi • Est. 1 h 49 m
Silas Road Trail is a 4.1 mile lightly trafficked loop trail located near Brewster, Massachusetts that features beautiful wild flowers and is rated as moderate. The trail is primarily used for hiking,Show more
#3 - Nickerson State Park Long Trail
Nickerson State Park
hardYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(50)
Length: 9.4 mi • Est. 4 h 12 m
Nickerson State Park Long Trail is a 9.4 mile out and back trail located near Brewster, Massachusetts that features a lake and is rated as difficult. The trail is primarily used for hiking, nature triShow more
#4 - Eagle Point Blue Trail
Punkhorn Parklands
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(45)
Length: 4.7 mi • Est. 2 h 2 m
Eagle Point Blue Trail is a 4.7 mile moderately trafficked out and back trail located near Brewster, Massachusetts that features a lake and is rated as moderate. The trail is primarily used for hikinShow more
#5 - Higgins Pond Loop
Nickerson State Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(38)
Length: 2.2 mi • Est. 1 h
Higgins Pond Loop is a 2.2 mile moderately trafficked loop trail located near Brewster, Massachusetts that features a lake and is good for all skill levels. The trail is primarily used for hiking, walShow more
#6 - Cliff Pond and Little Cliff Pond Loop
Nickerson State Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(15)
Length: 2.5 mi • Est. 1 h 6 m
Cliff Pond and Little Cliff Pond Loop is a 2.5 mile moderately trafficked loop trail located near Brewster, Massachusetts that features a lake and is good for all skill levels. The trail offers a numShow more
#7 - Lee Baldwin Loop
Cape Cod Museum of Natural History
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(20)
Length: 0.7 mi • Est. 19 m
Lee Baldwin Loop is a 0.7 mile loop trail located near Brewster, Massachusetts that offers the chance to see wildlife and is good for all skill levels. The trail is primarily used for hiking, walking,Show more
#8 - Punkhorn Yellow and Orange Loop
Punkhorn Parklands
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(54)
Length: 1.8 mi • Est. 47 m
Punkhorn Yellow and Orange Loop is a 1.8 mile moderately trafficked loop trail located near Brewster, Massachusetts that features a lake and is good for all skill levels. The trail is primarily used Show more
#9 - Cliff Pond And Forest Loop Trail
Nickerson State Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(6)
Length: 3.3 mi • Est. 1 h 28 m
Cliff Pond And Forest Loop Trail is a 3.3 mile lightly trafficked loop trail located near Brewster, Massachusetts that features a lake and is good for all skill levels. The trail is primarily used forShow more
#10 - Woodlands Trail
Sheep Pond Woodlands
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(19)
Length: 1.4 mi • Est. 37 m
Woodlands Trail is a 1.4 mile moderately trafficked out and back trail located near Brewster, Massachusetts that features a lake and is good for all skill levels. The trail is primarily used for hikinShow more
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