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

Cheshire, Mass.

Home of “The Father Tom Campsite”
Available for A.T. hikers only

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 ten years, community building has blossomed in Cheshire through the efforts of the Cheshire Community Association (CCA), a 501c3 grassroots organization. One event “Climb the Cobbles”, 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, and most recently the creation of the “Father Tom Campsite” exclusively for A.T. hikers.

Here’s what hikers have to say about the Father Tom Campsite…

~ Hands down the #1 Town hiker campsite on the entire AT. Great model for other towns. Thank you Thank you
~ Wow this is such a sweet blessing to happen upon! Thank you for a place to recharge before tackling the mountain!
~ Thank you Cheshire Community for this wonderful ministry you continue in the name of Father Tom! Your service to the hiking community is a greater blessing than you can know. God Bless you!
~ Thank you Cheshire for this wonderful campsite! The bikes are an incredible touch. ☺
~ Five Star Campsite! Thanks!

Plan Your Visit

The Father Tom Campsite is located across the street from Diane’s Twist, heading NOBO on AT, go left before the Cheshire snow plow. The entrance is on the left. For use by individual hikers only, no organized groups. 12 tents and 2 night stay, maximum. Space for 3 hammocks, bikes available. Port-a-potty, municipal water, and electricity available. No smoking/alcohol/drugs of any kind. No fires. Open May 1 – Oct. 30. No reservations needed. Sponsored by the Cheshire Community Association. For more info contact Eileen – 413 717 0673.

The Ashuwillticook Rail Trail extends 14 miles from Pittsfield, through Lanesborough and 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.

Get Involved

AMC Western Massachusetts

The AMC Western 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