Best trails in Chester

423 Reviews
Looking for a great trail near Chester, Massachusetts? AllTrails has 5 great hiking trails, forest trails, 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 Mount Riga State Park or Mount Holyoke Range State Park, we've got you covered. You'll also find some great local park options, like Mount Greylock State Reservation or Mount Everett State Reservation. Ready for some activity? There are 5 moderate trails in Chester ranging from 1.9 to 5.4 miles and from 515 to 1,466 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 Chester
Top trails (5)
#1 - Keystone Arch Bridges Trail
Walnut Hill Wildlife Management Area
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(144)
Length: 4.5 mi • Est. 2 h 10 m
Keystone Arch Bridges Trail is a 4.5 mile moderately trafficked out and back trail located near Chester, Massachusetts that features a waterfall and is rated as moderate. The trail offers a number of Show more
#2 - Sanderson Brook Falls Loop
Chester Blandford State Forest
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(158)
Length: 4.8 mi • Est. 2 h 40 m
The route shown here traverses the H. Newman Marsh Trail, Memorial Trail, Mica Mine Road, Observation Hill Road, C.C.C. Trail, and the Sanderson Brook Road. The falls are near the intersection of the Show more
#3 - Sanderson Brook Falls Trail
Chester Blandford State Forest
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(82)
Length: 1.9 mi • Est. 59 m
This route traverses the unpaved Sanderson Brook Road to the falls and then returns to the parking area. The road is closed to motor vehicles. Hikers wishing to extend their hike could make this intoShow more
#4 - Memorial Trail via H. Newman Marsh Trail
Chester Blandford State Forest
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(24)
Length: 2.2 mi • Est. 1 h 27 m
The route shown here is a quick climb up to some sweeping vistas along the Memorial Trail. There are other trails and sights including the Sanderson Brook Falls in this area, if you wish to extend youShow more
#5 - Beulah Land Road Loop via Sanderson Brook Road
Chester Blandford State Forest
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(12)
Length: 5.4 mi • Est. 2 h 53 m
Beulah Land Road Loop via Sanderson Brook Road is a 5.4 mile moderately trafficked loop trail located near Chester, Massachusetts that offers the chance to see wildlife. The trail is rated as moderateShow more