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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