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Best trails in Chester

151 Reviews
Explore the most popular trails near Chester with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.
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Map of trails in Chester
Top trails (4)
#1 - Pattaconk Reservoir
Cockaponset State Forest
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(100)
Length: 2.7 mi • Est. 1 h 13 m
Pattaconk Reservoir is a 2.7 mile moderately trafficked loop trail located near Chester, Connecticut that features a lake and is good for all skill levels. The trail offers a number of activity optionShow more
#2 - Blue Cockaponset Trail
Cockaponset State Forest
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(31)
Length: 5.2 mi • Est. 2 h 23 m
Blue Cockaponset Trail is a 5.2 mile moderately trafficked loop trail located near Chester, Connecticut that features a lake and is good for all skill levels. The trail offers a number of activity optShow more
#3 - Cockaponset Trail and Pattaconk Loop
Chester, Connecticut
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(11)
Length: 7.6 mi • Est. 3 h 37 m
There is parking on Rte 148, room for 5 or 6 cars on the other side of the road from the trailhead. Take the blue-blazed Cockaponset Trail as far as Old County Road, 4 miles, and then return via the bShow more
#4 - Blue Cockaponset Trail
Cockaponset State Forest
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(9)
Length: 6.9 mi • Est. 3 h 19 m
Blue Cockaponset Trail is a 6.9 mile point-to-point trail located near Chester, Connecticut that features a lake and is rated as moderate. The trail is primarily used for hiking, walking, and running.Show more