Eat

Diane's Twist

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

Address: 13 Main St
Getting there: take Church St off MA Rt 8, or Wells Rd off of MA Rt 116; if on the Appalachian Trail, take Fisk St and then Railroad St toward the Father Tom Campsite and the shop will be right there on Main St across from the campsite.
Hours: daily 11AM-PM

Updated 28 Sept 2026. Something wrong? Tell us.

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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
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.
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.
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.