Cheshire is a town in the Berkshire Hills region of Massachusetts.
- Ashuwillticook Rail Trail A 10-foot wide, 11 mile paved rail trail path. The Ashuwillticook (ash-oo-will-ti-cook) Rail Trail runs parallel to Route 8 through the towns of Cheshire, Lanesborough and Adams. The southern end of the trail begins at the entrance to the Berkshire Mall off Route 8 in Lanesborough. The northern end is at Adams center. The Trail passes Cheshire Reservoir, the Hoosic River, and several wetland habitats with abundant wildlife. Parking lots and restrooms are available along the way. A pamphlet with maps is widely available.
- Appalachian Trail
- Cheshire Guest House, Lanesboro Road, ☎ 1 413 743 4918, . Quiet country setting,backyard with gardens and a stream. 3 bedrooms 1 bath, Sleeps 6, Laundry room, Cable TV, High speed Internet, cell phone reception.4 miles to the Berkshire Mall, 10 minutes to Pittsfield MA.