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Best trails in Cheshire

592 Reviews
Looking for a great trail near Cheshire, Massachusetts? AllTrails has 7 great hiking trails, views 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 Peebles Island State Park or Grafton Lakes State Park, we've got you covered. You'll also find some great local park options, like Mount Greylock State Reservation or Mount Tom State Reservation. Ready for some activity? There are 6 moderate trails in Cheshire ranging from 1.7 to 7.5 miles and from 961 to 3,490 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 Cheshire
Top trails (7)
#1 - Mount Greylock and Saddle Ball Mountain
Mount Greylock State Reservation
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(232)
Length: 7.5 mi • Est. 4 h 12 m
#2 - Cheshire Cobbles via Appalachian Trail
Chalet Wildlife Management Area
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(131)
Length: 2.9 mi • Est. 1 h 11 m
#3 - Rounds Rock Trail
Mount Greylock State Reservation
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(59)
Length: 0.9 mi • Est. 26 m
#4 - Appalachian Trail: Dalton to Cheshire
Chalet Wildlife Management Area
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(52)
Length: 7.3 mi • Est. 3 h 52 m
#5 - The Cobbles via Appalachian Trail
Cheshire, Massachusetts
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(48)
Length: 1.7 mi • Est. 1 h 10 m
#6 - Cheshire Cobbles Loop
Chalet Wildlife Management Area
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(42)
Length: 4.1 mi • Est. 2 h 18 m
#7 - Saddle Ball Mountain via Appalachian Trail
Mount Greylock State Reservation
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(7)
Length: 7.3 mi • Est. 4 h 5 m
This is a great opportunity to enjoy the Mt Greylock Reservation without actually following the crowds that go around the Greylock summit. The trail starts easy, going downhill on easy trails. Upon reaching the Cheshire Harbor trail, the trail gets a bit rough, and gains some elevation quickly. To return, you will use a nice portion of the Appalachian Trail. From Saddle Ball Mountain you can see beautiful views of Mt. Greylock, and just south of the mountaintop you will find another vista spot that will allow you to see upstate New York. There is plenty of opportunities to enjoy the flora and fauna of Massachusetts. Almost all of the microclimates are represented. Plenty of varieties of trees. And at the end of the hike, on the Jones Nose trail you can enjoy bird watching on a lightly wooded area (mostly a plain with beautiful wildflowers and scattered trees).Show more