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Cheshire (Massachusetts)
Wikivoyage guide · 18 sections
▸Introduction368 chars
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.
▸By car466 chars
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.
▸By bus321 chars
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/
▸On foot462 chars
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.
▸On bicycle140 chars
The Ashuwillticook Rail Trail is open to bicycle, though snowfall during late fall into early spring sometimes renders the trail impassable.
▸Get around581 chars
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.
▸See2,409 chars
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, admin@cheshire-ma.gov. 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). 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. (updated Nov 2025)
6 Cheshire's Mammoth Cheese Monument, 95 School St (at the junction of Church St and School St). Nearly life-size replica of the gigantic cheese that the town of Cheshire gave President Thomas Jefferson in 1802 (updated Nov 2025)
▸Water activities716 chars
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)
▸Range shooting624 chars
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)
▸Outdoor trail and wilderness678 chars
5 Rounds Rock Trailhead, 14-18 Rockwell Rd (take W Mountain Rd off of MA Rt 8 to the terminus at Greylock Rd. Turn right onto Greylock Rd.; continue to the terminus at Rockwell Rd and then turn left onto Rockwell Rd; continue to the destination; Rockwell Rd can also be accessed from Lanesborough via Greylock Rd off of N Main St). A hiking trail that is part of the Mount Greylock State Reservation. (updated Nov 2025)
6 Stafford Hill Wildlife Management Area, Stafford Hill Road, ☏ +1 413-684-1646. 1440-acreage of forest and field wildlife preserve. (updated Nov 2025) 7 Stafford Hill Wildlife Management Area Parking (North), Stafford Hill Road. North lot (updated Nov 2025)
▸Chalet Wildlife Area1,483 chars
8 Chalet Wildlife Area, ☏ +1 413-684-1646. 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. (updated Nov 2025)
9 Cheshire Cobble Trailhead (Chalet Wildlife Management Area Notch Road Parking), Notch Rd (near the junction with Windsor Rd.; take E Main from Church St.; E Main will become Windsor Rd.; turn right at the junction; the parking area is just past the junction), ☏ +1 413-684-1646. 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. (updated Nov 2025)
10 Chalet Wildlife Management Area West Parking, S State Rd (off of MA Rt 8 (S State Rd); turn right onto the road to the car dealer plaza and immediately turn right again onto the driveway for the parking lot). West parking lot for Chalet Wildlife Management Area (updated Nov 2025)
11 Chalet Wildlife Management Area Windsor Road Parking, Windsor Rd (take Windsor Rd from E Main St in Cheshire. Alternatively, take Stafford Hill Road from the junction with Rt 116 Savoy Rd and Wells Rd. At the junction with Windsor Rd, turn right onto Windsor Rd). Windsor Road Parking Lot for Chalet Wildlife Management Area. (updated Nov 2025)
▸Ashuwillticook Rail Trail1,362 chars
12 Ashuwillticook Rail Trail, ☏ +1 413-499-7003. 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. (updated Oct 2025)
1 Nobodys Rd, 18-22 Nobodys Rd. No formal parking; Nobodys Rd is a dead-end with space to park on the side of the road. (updated Oct 2025)
2 Farnham Rd, Farnams Rd (access road cuts through the Cheshire Reservoir). (updated Oct 2025)
3 Route 8 crossing (junction with Route 8). (updated Oct 2025)
4 Railroad St, Railroad St (junction of Railroad St with Church St, Main St, and the Appalachian trail), ☏ +1 413-442-8928. (updated Oct 2025)
▸Appalachian Trail1,533 chars
13 Appalachian Trail. (updated Nov 2025) Entry and exit points, as well as an exclusive campsite, are as follows:
1 Appalachian Trail at Outlook Ave, Outlook Ave. (updated Oct 2025)
2 Appalachian Trail at MA Rt 8 North St, MA Rt 8 (North St). The trail crosses MA Rt 8 here (updated Nov 2025)
3 Appalachian Trail at Fisk St, Fisk St junction with School St. The trail begins running concurrent with Fisk St here, at the junction with School St (updated Nov 2025)
1 Father Tom Campsite, 6 Main St (from the beginning of the Fisk St concurrence, go on Fisk St and then turn right onto Railroad St.; continue until you reach the junction with Church St, Main St, and the Ashuwillticook Rail Trail; the camp is south, across Church St/Main St, behind the Ashuwillticook Rail Trail parking lot). A campsite in the center of town exclusive to Appalachian Trail hikers. Open mid-May to the end of October. (updated Nov 2025)
4 Appalachian Trailhead at Furnace Hill, Furnace Hill (take Main St east across the bridge over the Hoosic River, at the fork in the road take the right onto E Main St, then turn right onto Furnace Hill; continue to the terminus of Furnace Hill, then enter the trailhead). (updated Nov 2025)
1 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. (updated Nov 2025)
▸Buy426 chars
1 Whitney's Farm Market & Garden Center, 1775 S State Rd (MA Rt 8), ☏ +1 413-442-4749. 9AM-6PM daily. Large farm and garden center that includes seasonal pick-your-own fruit orchards and fields (updated Nov 2025)
2 Cheshire Glassworks, 24 South St (MA Rt 8), ☏ +1 413-743-7828, jill@cheshireglassworks.com. Tu 9AM–5PM, W 11AM–5PM, Th F noon–5PM, Sa 11AM–5PM. Handmade jewelry and beads created by the owner. (updated Nov 2025)
▸Eat931 chars
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)
▸Sleep155 chars
1 Harbour House Inn (Elements Hotel & Spa), 725 North State Road, ☏ +1 413 743-8959, harbourhouseinn@aol.com.
There are also listings on AirBnB and VRBO.
▸Cope561 chars
1 Cheshire Public Library, 23 Depot St, ☏ +1 413-743-4746, Cheshire@cwmars.org. M Th 10AM-2PM, Tu noon-7PM, W noon-5PM. Town library. Requires a library card. (updated Nov 2025)
2 Cheshire Post Office, 214 Church St, ☏ +1 413-743-3184, toll-free: +1 800-275-8777. M-F 7:30AM–1PM, 2–4:30PM; Sa 8:30AM-11:30AM. United States Postal Service office in Cheshire. Useful for posting ahead supplies if you are taking the Appalachian Trail. Its position on Church St is conveniently concurrent with the trail as it runs through Cheshire town center. (updated Nov 2025)
▸Go next484 chars
Visit neighboring Adams, New Ashford, Savoy, Windsor, and Lanesborough, or the nearby cities of Pittsfield and North Adams or the nearby towns of Hancock and Williamstown. Further north is Bennington, Vermont and further south are Lee, Stockbridge, and Great Barrington. Westward is Albany and the New York Capital District, and east is Springfield and Amherst. If on the Appalachian Trail, north are New Ashford and Williamstown, and south are Washington, Becket, Tyringham, and Lee.
Facts
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Source
WBP almanac