Appalachian Trail: Dalton to Cheshire is a 7.3 mile lightly trafficked point-to-point trail located near Cheshire, Massachusetts that offers the chance to see wildlife. The trail is rated as moderate and primarily used for hiking, trail running, camping, and backpacking. Dogs are also able to use this trail but must be kept on leash.

DISTANCE
7.3 miles
ELEVATION GAIN
1,361 feet
ROUTE TYPE
Point to Point

dogs on leash

backpacking

camping

hiking

trail running

forest

views

wildlife

hiking
9 months ago

Good hike. Not sure why its listed as hard? Ive done this hike probably 20 times (Im local). It is 7+ miles, but not too strenuous. Cheshire to Dalton is a bit harder, because you do much more climbing, including climbing to the cobbles in the beginning. There is also a shelter with a privy about half way.

hiking
Tuesday, October 10, 2017

Nice hike. I'd put it more in the moderate category. I took the BRTA Bus to Main St in Dalton and walked to the trailhead on Gulf RD. Took me 4 hr 40 min (to the Cheshire Post Office bus stop) with 10 minutes at Gore Pond and 30 minutes at Cheshire Cobbles admiring the foliage finally coming in. Bus back to Pittsfield.

hiking
Friday, July 14, 2017

I hiked this on a misty, foggy day, which made Gore Pond (about halfway) look like that place where Yoda lives. The view of Cheshire from the "cobbles" was diminished, but still worth the climb from either direction. A fun 5 hours!

hiking
Sunday, July 02, 2017

hiking
Wednesday, June 28, 2017

hiking
Sunday, April 30, 2017