Cheshire joins three other Berkshire towns as Appalachian Trail Communities: Great Barrington, North Adams, and Dalton.
"There are over 40 communities along the Appalachian Trail's corridor that have been recognized in The Appalachian Trail Community™ program. These towns and cities are considered assets by all that use the A.T., and many of these towns act as good friends and neighbors to the Trail. As a visitor on the Trail, you can enjoy special events and promotions in these designated areas." - Appalachian Trail Conservancy
- July 3, 2018: Cheshire Celebrates Appalachian Trail Community Designation
- May 14, 2018: Cheshire Designated As Appalachian Trail Community