Cheshire, MA Road Trips

1 Stafford Hill Memorial, HVFM+RR Cheshire, Massachusetts (Stafford Hill Rd/Wells Rd) (accessed on foot from the Stafford Hill Wildlife Area South parking lot.), ☏ +1 413-743-1690 x100, [email protected]. A stone monument on the burial site of Joab Stafford, a founding settler of Cheshire. (updated Nov 2025) 2 Old Churchyard Cemetery (Jenks Road Cemetery / Stafford Hill Cemetery), 918 Jenks Rd (take Jenks Rd off of Wells Rd; access Wells Rd from either Main St in Cheshire town center or MA 116 to the northeast). 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. (updated Nov 2025) 3 Cheshire Town Hall, 191 Church St, ☏ +1 413-743-1690. 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. (updated Nov 2025) 4 Hall's Tavern, 41 North St (MA Rt 8). 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. (updated Nov 2025) 5 Farnams Village Historic District, Lanesboro, Quarry, and Farnam Rds (if coming from Lanesborough, take Summer St, then turn onto Old Cheshire Rd; the destination is where this becomes Lanesborough Rd. If coming from MA Rt 8 in Cheshire, take either Lanesboro Rd near the town center, or, further south, Farnams Rd across Cheshire Reservoir to the junction with Lanesboro Rd).

1 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. (updated Nov 2025) 2 Cheshire Lake Boat Ramp, S State Rd (MA Rt 8) (right on Rt 8, at the Cheshire Reservoir Lookout and parking lot on the northern tip of the reservoir). Boat launch for the northern half of the reservoir. (updated Nov 2025) 3 Cheshire Boat Ramp, Farnams Rd (access Farnams Rd from MA Rt 8 to the east or Lanesboro Rd on the west side). Boat launch for the southern half of the reservoir. Also works as a small swim beach. (updated Nov 2025) 4 Cheshire Road and Gun Club, 310 Curran Rd (from Rt 8, take W Mountain Rd; at the junction with Greylock Rd, turn left onto Greylock Rd. Continue and Curran Rd will be on the right; or, take Greylock Rd from N Main St in Lanesborough; turn onto Quarry Rd, which will turn into W Mountain Rd. Curran Rd will be on the left; Quarry Rd/W Mountain Rd on the Lanesborough side is closed Dec-May), ☏ +1 413-743-3700. M-F 10AM-2PM; Sa noon-5PM. 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 (updated Nov 2025) 5 Rounds Rock Trailhead, 14-18 Rockwell Rd (take W Mountain Rd off of MA Rt 8 to the terminus at Greylock Rd.

1 Common Table Food and Drink, 287 S State Rd (MA Rt 8), ☏ +1 413-776-7141. Tu-Th 4-9PM, F Sa 4-10PM. Pub-style food and bar. Reservation link: https://resy.com/cities/cheshire-ma/venues/common-table $20-30. (updated Nov 2025) 2 Snack Shack, 111 Farnams Rd (take either MA Rt 8 in Cheshire or Old Cheshire Rd off of Summer St in Lanesborough: continue until Farnams Rd, a causeway across Cheshire Reservoir). Summer hours noon-8PM. Serves Uncle Louie G Gourmet Italian Ices, and also food and beverages. Has live music throughout the summer. (updated Nov 2025) 3 Diane's Twist, 13 Main St (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.), ☏ +1 413-743-9776. daily 11AM-PM. Ice cream and dessert shop on the Appalachian Trail and Main St. (updated Nov 2025)

1 Harbour House Inn (Elements Hotel & Spa), 725 North State Road, ☏ +1 413 743-8959, [email protected]. There are also listings on AirBnB and VRBO.

MA Route 8 runs through Cheshire, with Adams to the north and Lanesborough to the south. Lanesborough also runs parallel with the lower half of the western border of Cheshire, and Route 8 can be accessed via US Route 7 from Lanesborough via Old Cheshire Rd off of Summer St. MA Route 116, which originates in Springfield, cuts through northeast Cheshire as it goes from Savoy to Adams. Taking Wells Road off of Route 116 will take you to the town center of Cheshire. The Route 1 line operated by Berkshire Regional Transit Authority stops in Cheshire Center on Railroad St, near the post office. The line runs from Pittsfield to North Adams and makes stops in Lanesborough and Adams. The schedule can be found on the BRTA website: https://berkshirerta.gov/plan-your-trip/route-1-schedule/ You can enter along the Appalachian Trail: from the north take the trail from Mt. Greylock, either in Adams or Williamstown, south into Cheshire, passing through New Ashford (there are no exits on the New Ashford portion). If coming from the south, enter from Dalton. You can also enter from Adams on the Ashuwillticook Rail Trail, and south by the same trail from Berkshire in Lanesborough. Be mindful that snow and ice can make the path treacherous to walk on. The Ashuwillticook Rail Trail is open to bicycle, though snowfall during late fall into early spring sometimes renders the trail impassable.

The best way to get around Cheshire is by car. Most destinations are in the town center or on MA Route 8. You can also traverse the town on foot via the Ashuwillticook Rail Trail. Similarly, the Appalachian Trail runs through the town and has multiple entry and exit points, including in the town center. Much of the Cheshire town center area is paved or otherwise easily navigable on foot. The Ashuwillticook Rail Trail also allows bicycles, and the town center area can be entered and navigated on bicycle; there are no designated bike lanes off of the Ashuwillticook Rail Trail.