Cheshire was first settled in 1766 and officially incorporated in 1793.

Cheshire, Mass.

Cheshire has long been a hiker–friendly town. Serving as a central location for all kinds of A.T. hikers as well as cycling and walking on the Ashuwillticook Rail Trail, which intersects the A.T. right in town.

Cheshire is a starting point for A.T. day hike destinations. The Cobbles (1.1 miles south) is a vista with sweeping views of Mt Greylock, Cheshire Lake, the town and surrounding countryside. A similar distance north, an open farm field offers views east, and a 30ft. high glacial erratic, Reynolds Rock. The town also serves as a starting location with ample parking for more ambitious hikes to the summit of Mt Greylock, 7.7 miles north on the A.T.

Over the past five years, community building has blossomed in Cheshire. The Cheshire Community Association (CCA) was born, (a 501c3 grassroots organization, dedicated to building community) and more recently the Cheshire Community Action Team (CAT) was formed. These groups initiated a community event “Climb the Cobbles”, which introduced several residents to the A.T. for the first time. Since then, participants have taken an interest in making Cheshire an A.T. Community. That initiative became official in June 2018. The local A.T. committee worked with the Mass AT Committee to officially adopt the Cobbles, and the adjacent section of the trail.

Will forever remember your town for providing shelter from the worst thunderstorm I experienced during my hike. Glad to see this!”  . . . Mike Vogel

“I stayed in Cheshire 3 nights while hiking the trail a few months ago. In fact, I had a melanoma under my backpack strap and the woman who lived directly across the cathedral, where I slept, was a great trail angel. She drove me to the surgeon in Pittsfield who excised my melanoma. So, your little community is dear to me…so is the gal at the general store there. Love the lake. Good luck. If you need a volunteer to come and work in a hostel, let me know.” . . . Peace, Kay Rutherford

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The Ashuwillticook Rail Trail extends 13 miles from Lanesborough, through Cheshire, passing by the beautiful Cheshire Lake, continues through and ends in Adams. The A.T. directly intersects the Rail Trail right in town. Residents and visitors enjoy running, cycling and walking on this beautiful trail.

Cheshire Lake is another recreation resource for kayaking, canoeing, paddleboard, swimming, fishing, and boating. In the winter the Ice Fishing Derby is also a popular event.


These businesses support the Trail by taking part in the A.T. Community Supporter program.

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AMC Berkshire

AMC Berkshire’s ‘Massachusetts Appalachian Trail Management Committee’ is responsible for the maintenance, management, and protection of the almost 90 miles of Appalachian Trail within Massachusetts, coordinating the extensive volunteer effort that keeps the trail open and beautiful. Learn more and become a member today at

Appalachian Trail Conservancy

ATC Volunteer Program

The Appalachian Trail Conservancy is always looking for dedicated volunteers to help maintain the A.T. and assist in our visitor center and headquarters. Opportunities range from greeting visitors and providing information about local hikes to joining a Trail crew for week-long maintenance trips, gaining first-hand experience in what it takes to keep the A.T. open and enjoyable for millions each year. Learn more at