Ashuwillticook Rail Trail Massachusetts Department of Conservation and Recreation Ashuwillticook Rail Trail - Railroad Street
Railroad Street, Cheshire, MA

Activites & Features
Information
  • Accessible
  • Dogs allowed
  • Family Friendly
  • Free
  • Near Public Transit
  • Parking
  • Trailhead
Safety Tips
Ashuwillticook Rail Trail - Railroad Street in Cheshire, MA | Berkshires Outside
Ashuwillticook Rail Trail - Railroad Street in Cheshire, MA | Berkshires Outside
Ashuwillticook Rail Trail - Railroad Street in Cheshire, MA | Berkshires Outside
Ashuwillticook Rail Trail - Railroad Street in Cheshire, MA | Berkshires Outside
  • Public Land
  • Private Land
  • Bus Route
  • Trail
  • Major Trail

About Ashuwillticook Rail Trail - Railroad Street

The Railroad Street trailhead for the Ashuwillticook Rail Trail is in downtown Cheshire, a quaint Western Massachusetts town designated as an Appalachian Trail Community. The Ashuwillticook Rail Trail is a 10-foot wide paved, flat path running from Pittsfield to North Adams. The path's smooth pavement is ideal for biking, jogging, or rollerblading, and its surrounding greenery makes the trail perfect for a peaceful walk or even a site for top-tier birding. Snowshoeing is possible during winter and may be favorable on the flat terrain. At Railroad Street, travelers will also cross the Appalachian Trail, which can be taken south through Cheshire Cobble or "The Cobbles," and offers scenic views of Cheshire and Mount Greylock.

Also noteworthy are the benches that line the trailhead at the Railroad Street parking area, allowing visitors to rest or picnic at either end of their journey. Visitors can also find a rest stop where the trail runs alongside Cheshire Reservoir or the Hoosic River - "Ashuwillticook" translates to "river between the hills."

The Ashuwillticook Rail Trail requires users to be courteous to all other visitors and to use the trail cautiously. Proper trail etiquette includes leashing pets, cleaning waste or garbage, stopping at stop signs, and moving on the trail at reasonable speeds.

Massachusetts Department of Conservation and Recreation

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Railroad Street, Cheshire, MA

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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.

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