Cheshire

Cheshire is a town in the Berkshires of Massachusetts. Portions of the town are on Mount Greylock and must be accessed from adjacent towns if traveling by vehicle. Cheshire has a small population; restaurant and lodging options are limited, but the town has extensive offerings for outdoor activities including hiking, cycling, boating, swimming, fishing, and hunting.

See: 7
Do: 21
Eat: 3
Buy: 2

21 places match

Appalachian Trail

Entry and exit points, as well as an exclusive campsite, are as follows:

Ashuwillticook Rail Trail

A 10-foot wide, 11-mile long 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. Walking, cycling, and rollerblading are all common activities, the trail is pet-friendly and wheelchair accessible. Accessibility for the respective activities and disability can be limited by seasonality and weather. Cheshire has multiple access points for the trail. Access points with parking are listed below.

Chalet Wildlife Area

Nearly 8,000 acres of forest stretched across Cheshire, Dalton, Lanesborough, and Windsor. Open for fishing, hunting, trapping, hiking, and wildlife viewing. For hiker safety, hunting is not allowed in the hiking trail areas.

Chalet Wildlife Management Area Windsor Road Parking

Windsor Road Parking Lot for Chalet Wildlife Management Area.

Cheshire Boat Ramp

Boat launch for the southern half of the reservoir. Also works as a small swim beach.

Cheshire Cobble Trailhead

Chalet Wildlife Management Area Notch Road Parking

East parking lot for the Chalet Wildlife Area, and the trailhead for the Cheshire Cobble Trail. Cheshire Cobble Trail goes west uphill to a junction with the Appalachian Trail at The Cobbles, which offers a breathtaking view of the town and surrounding hillsides.

Cheshire Reservoir

A dammed portion of the Hoosic River that offers boating, swimming, and fishing activities. It is bisected by Farnams Rd, which is a barrier to watercraft. There are boat launches for the northern and southern halves of the reservoir.

Cheshire Road and Gun Club

Shooting ranges for guns and archery; memberships required. One guest is permitted if accompanied by a member. Memberships can be purchased at Cheshire Sporting Goods

Mon-Fri 10AM-2PM; Sat noon-5PM