Parks and the outdoors in Cheshire

16 parks, gardens, beaches and walks in and around Cheshire.

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
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.
Eat
Diane's Twist
Ice cream and dessert shop on the Appalachian Trail and Main St.
daily 11AM-PM
Do
Rounds Rock Trailhead
A hiking trail that is part of the Mount Greylock State Reservation.
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.
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 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

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