Things to do in Cheshire

21 activities, venues and outings in Cheshire, from theatres and live music to parks and tours.

Ranked with the travel guide's picks and well-known places first.

Do
Appalachian Trail
Entry and exit points, as well as an exclusive campsite, are as follows:
Do
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.
Do
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.
Do
Chalet Wildlife Management Area Windsor Road Parking
Windsor Road Parking Lot for Chalet Wildlife Management Area.
Do
Cheshire Boat Ramp
Boat launch for the southern half of the reservoir. Also works as a small swim beach.
Do
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.
Do
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.
Do
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
Do
Rounds Rock Trailhead
A hiking trail that is part of the Mount Greylock State Reservation.
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.
Do
Chalet Wildlife Management Area West Parking
West parking lot for Chalet Wildlife Management Area
Do
Cheshire Lake Boat Ramp
Boat launch for the northern half of the reservoir.
Do
Stafford Hill Wildlife Management Area
1440-acreage of forest and field wildlife preserve.
Do
Stafford Hill Wildlife Management Area Parking (North)
North lot
Do Not mapped
Appalachian Trail at MA Rt 8 North St
The trail crosses MA Rt 8 here
Do Not mapped
Appalachian Trail at Outlook Ave
Outlook Ave
Do Not mapped
Appalachian Trailhead at Furnace Hill
Furnace Hill
Do Not mapped
Farnham Rd
Farnams Rd
Do Not mapped
Railroad St
Railroad St
Do Not mapped
Route 8 crossing

Listings from the Wikivoyage guide to Cheshire (CC BY-SA 4.0).