Overview
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.
7 sights · 21 things to do · 3 places to eat · 2 places to stay
Updated from Wikivoyage on 1 October 2026 · Something wrong or missing? Improve it on Wikivoyage
Best things about Cheshire
Stafford Hill Memorial
A stone monument on the burial site of Joab Stafford, a founding settler of Cheshire.
Old Churchyard Cemetery
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.
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.
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.
Farnams Village Historic District
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 Lanes…
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 …
Plan your trip
Best time to visit & weather
Most comfortable: May–Oct. Summer highs reach about 84°F; winter lows dip to about 16°F. Cold months (Jan, Feb, Dec) can bring snow and ice; check road conditions. Wettest: Jul and Jun. (climate data from nearby Albany)
Blue bars: average daily high and low (°F). Purple columns: average monthly rain and melted snow (inches).
Getting there
- From you: to see whether to drive or fly, and how long it takes.
- ALB Albany International Airport, Albany — 35 mi away (major hub). Directions
- BDL Bradley International Airport, Hartford — 49 mi away (major hub). Directions
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.
Full “Get in” guide ↓Budget & where to stay
No prices are listed for this place yet. See the Sleep guide ↓ for options.
Sample 3-day itinerary
Day 1
- Morning Cheshire Town Hall, Cheshire's Mammoth Cheese Monument, Ashuwillticook Rail Trail
- Lunch Common Table Food and Drink
- Afternoon Cheshire Lake Boat Ramp, Chalet Wildlife Management Area West Parking
- Dinner Diane's Twist
Day 2
- Morning Stafford Hill Memorial, Stafford Hill Wildlife Management Area, Stafford Hill Wildlife Management Area Parking (North)
- Lunch Snack Shack
- Afternoon Old Churchyard Cemetery, Farnham Rd
Day 3
- Morning Cheshire Cobble Trailhead, Chalet Wildlife Management Area Windsor Road Parking
- Afternoon The Cobbles, Route 8 crossing
Stops are grouped by area so each day needs little backtracking. Check opening hours before you go.
Food for you
Cuisine (tap to filter)
What to ask about, for your diet
Diet labels come from each listing's description and cuisine; “likely” means the cuisine usually has good choices, not a promise. Check with the restaurant. Open the food finder
Photos
Map
Every listing with a location. Tap a pin for its Google Maps link.
Get in
By car
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 bus
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 foot
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 bicycle
The Ashuwillticook Rail Trail is open to bicycle, though snowfall during late fall into early spring sometimes renders the trail impassable.
Get around
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.
See
See Old Churchyard Cemetery (Jenks Road Cemetery / Stafford Hill Cemetery)
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.
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.
See Farnams Village Historic District
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.
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
Do
Water activities
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 Boat Ramp
Boat launch for the southern half of the reservoir. Also works as a small swim beach.
Range shooting
Outdoor trail and wilderness
Chalet Wildlife Area
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 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 Chalet Wildlife Management Area West Parking
West parking lot for Chalet Wildlife Management Area
Do Chalet Wildlife Management Area Windsor Road Parking
Windsor Road Parking Lot for Chalet Wildlife Management Area.
Ashuwillticook Rail Trail
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 Nobodys Rd
No formal parking; Nobodys Rd is a dead-end with space to park on the side of the road.
Do Farnham Rd
Do Route 8 crossing
Do Railroad St
Appalachian Trail
- Entry and exit points, as well as an exclusive campsite, are as follows:
Do Appalachian Trail
Do Appalachian Trail at Outlook Ave
Do Appalachian Trail at Fisk St
The trail begins running concurrent with Fisk St here, at the junction with School St
Do Appalachian Trailhead at Furnace Hill
See 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.
Buy
Eat
Eat Common Table Food and Drink
Pub-style food and bar. Reservation link: https://resy.com/cities/cheshire-ma/venues/common-table
Eat Snack Shack
Serves Uncle Louie G Gourmet Italian Ices, and also food and beverages. Has live music throughout the summer.
Eat Diane's Twist
Ice cream and dessert shop on the Appalachian Trail and Main St.
Sleep
There are also listings on AirBnB and VRBO.
Go next
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.
Nearby
Lanesborough
City / town · 30 listings · 5 mi away
Adams
City / town · 14 listings · 5 mi away
New Ashford
City / town · 11 listings · 5 mi away
Dalton
City / town · 51 listings · 6 mi away
Hancock
City / town · 25 listings · 8 mi away
Pittsfield
City / town · 39 listings · 9 mi away
Hinsdale
City / town · 21 listings · 9 mi away
North Adams
City / town · 12 listings · 10 mi away
My experience
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