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

Railroad Street, Cheshire, MA

About Ashuwillticook Rail Trail - Railroad Street

This trailhead for the Ashuwillticook Rail Trail starts visitors in the quaint Western Massachusetts town of Cheshire. Benches are lined along this part of the trail, making this area perfect for a rest or a lunchtime picnic. At Railroad Street, travelers will also cross the Appalachian Trail: a 2,000+ mile hiking trail from Georgia to Maine. On its way south, the trail leads to Cheshire Cobble or “The Cobbles,” which offers scenic views of Cheshire and Mount Greylock beyond. 

The Ashuwillticook Rail Trail, meanwhile, will bring visitors through a serene forest toward downtown Adams. During the summer, this section of the path turns into a green tunnel. Many wildlife species, especially birds, are visible from the trail as the weather warms. Going southward, visitors will eventually travel along the Cheshire Reservoir. There, scenic views of the Berkshires are extensive at all times of the year.

The Ashuwillticook Rail Trail is a family-friendly paved path from North Adams to Pittsfield. The trail was created from an old railroad line in the early 2000s. Visitors will find the trail ideal for biking, walking, wildlife viewing, or rollerblading. The name “Ashuwillticook” translates to “river between the hills.”

There are two parking areas for this section of the trail, both on Railroad Street as it crosses through downtown Cheshire.