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

33 places

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

See

Cheshire Town Hall

Built in 1898, the town hall complex is an example of Colonial Revival architecture. It is listed on the US National Register of Historic Places.

See

Cheshire's Mammoth Cheese Monument

Nearly life-size replica of the gigantic cheese that the town of Cheshire gave President Thomas Jefferson in 1802

Eat

Common Table Food and Drink

Pub-style food and bar. Reservation link: https://resy.com/cities/cheshire-ma/venues/common-table

Tue-Thu 4-9PM, Fri Sat 4-10PM$20-30

Eat

Diane's Twist

Ice cream and dessert shop on the Appalachian Trail and Main St.

daily 11AM-PM

See

Farnams Village Historic District

A National Register of Historic Places former limestone mining village. Farnams Village was a mining village whose associated mining and lime production was active from the 19th to mid-20th century. The junction of Lanesboro, Quarry, and Farnams Rds is the center of the former village. Remnants of the quarrying activities stretch west up onto Mt. Greylock, and can be accessed via Quarry Rd. Old equipment, work buildings, worker housing, and public buildings can be found. The area is of great interest to industrial archaeology. The village buildings display Greek Revival and Gothic architecture.

See

Hall's Tavern

Now a private residence, this building was once a tavern. Listed on the US National Register of Historic Places, it was built in 1804 and reflects the Federal architectural style of that period.

See

Old Churchyard Cemetery

Jenks Road Cemetery / Stafford Hill Cemetery

One of the oldest cemeteries in Cheshire and on the US National Register of Historic Places. Three of the first settlers of the town are known to be interred here.

Rounds Rock Trailhead

A hiking trail that is part of the Mount Greylock State Reservation.

Eat

Snack Shack

Serves Uncle Louie G Gourmet Italian Ices, and also food and beverages. Has live music throughout the summer.

Summer hours noon-8PM

See

Stafford Hill Memorial

A stone monument on the burial site of Joab Stafford, a founding settler of Cheshire.

Buy

Whitney's Farm Market & Garden Center

Large farm and garden center that includes seasonal pick-your-own fruit orchards and fields

9AM-6PM daily

Do Not mapped

Appalachian Trail at Fisk St

The trail begins running concurrent with Fisk St here, at the junction with School St

Do Not mapped

Nobodys Rd

No formal parking; Nobodys Rd is a dead-end with space to park on the side of the road.

See Not mapped

The Cobbles

View Mt Greylock, Cheshire Lake, the town, and surrounding countryside. Connects with the Cheshire Cobble Trailhead in Chalet Wildlife Area, which can serve as an entry and exit point. For the safety of hikers, this part of Chalet Wildlife Management Area does not permit hunting.