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Things to do in Cheshire

Southeast of Mount Greylock, Cheshire is an Appalachian Trail Community with approximately 6 miles of trail in the town, passing through on its way to the summit of Mount Greylock. Just 1.1 miles south of town on the Appalachian Trail, The Cobbles provides a panoramic view south of Cheshire Reservoir, Lanesborough, and Pittsfield.

The 14-mile Ashuwillticook Rail Trail also passes through the center of town, connecting Cheshire to Lanesborough and Pittsfield to the South, and Adams and North Adams to the north.  Popular with bikers, rollerbladers, joggers, and dog walkers, the trail passes by the eastern edge of Cheshire Reservoir.  At the northern edge of the reservoir, a parking lot provides access to both the rail trail and boat ramp/kayak launch that allows boaters and anglers access to the 418-acre reservoir.

  • Public Land
  • Private Land
  • Bus Route
  • Trail
  • Major Trail

Clubs, Retail & Rentals

Looking to meet up with others for team sports or group activities? Check out our list of clubs and leagues in the Berkshires. We also link to an array of outdoor recreation resources: retail shops for gear, rental facilities for equipment, and guides to get you where you want to go! Our list of summer camps will help you plan an overnight or day camp adventure for your young ones.