The Location

Berkshires is one of the most beautiful locations on the East Coast. Cheshire, and the surrounding towns have amazing activities to offer year round.

Year ‘Round:
Visit Mass Moca, Williams College Museum of Art, Clark Art Institute. Enjoy bargains as you shop at the area’s famous antique stores. Go to the movies in North Adams, Pittsfield, Williamstown and the Berkshire Mall. Enjoy the cultural richness of the area, contra dance in Lenox, Adams and Greenfield. Attend the region’s many folk music concerts and art festivals.

In the Summer, Fall and Spring:
Biking on the nearby Ashuwilticook bike trail, hiking on our own 70 acres or on the nearby Appalachian Trail, Mt. Greylock or Bartholomew’s Cobble. Swimming, kayaking or canoing on Cheshire’s many ponds and lakes. Pick in-season berries, apples and peaches at Cheshire’s abundant orchards. Browse nearby farmer’s markets. Take a picnic to Tanglewood and music festivals. Enjoy the area’s wonderful restaurants. Watch free family movies on North Adams’ green. Attend plays performed by Shakespeare and Co. and the Barrington Stage company. In the fall enjoy the brilliant colors of the Berkshire forests.

In the Winter:
Snowshoe or cross country ski the many trails that cover the nearby area. Snow shoe or ski directly from the house. Extensive alpine skiing is available within 3 miles at…. Also sking at Jiminy Peak resort, is only 35 minutes from the house.

Jiminy Peak
The Berkshires


Some of our personal recommendations for the area:


  • There are a lot of nice restaurants in the area. Williamstown has especially nice ones. There is a delicious Indian restaurant called Spice Root (413-458-5200.) There is also a Mexican restaurant, Coyote Flaco (413-458-4240). A few other are The Water Street Grill (413-458-4240) and good pizza at Hot Tomatoes Neapolitan Pizza (413-458-2722).
  • Pittsfield has some good places too. There are also a few coffee shops in the area if you are interested that offer breakfast and lunch, Dottie’s on North Street in Pittsfield and Cup & Saucer on Main Street in North Adams.

Farmer’s Markets

  • Williamstown Farmers’ Market
  • Saturdays 8-12, May 23-October
  • Spring St.
  • Pittsfield Farmers’ Market
  • Thursdays 4-7, May to October
  • 333 North St.
  • North Adams Farmers’ Market
  • Saturdays 8-12, July 12-October 25
  • 77 Holden St.
  • Adams Farmers’ Market
  • Fridays 12-6, May 29-October 23
  • 60 Columbia St.
  • Lanesboro Farmer’s Market                                                                          Wednesdays & Saturdays 8-2, May 2-November 21
  • Berkshire Mall Parking Lot near Sears, Route 8


  • If you take a right out of the driveway and drive up Sandmill Road, follow the paved road as it turns right, then head straight, still on paved road (that will be Windsor Road). You’ll pass some nice old working farms, sometimes see the border collies herding sheep, then, as the road heads downhill, you’ll take a hairpin left onto a dead end road. A parking lot (dirt) on the right before you reach a little pond. This is the trail head to the Cobble. Follow it up and up, beautiful rock outcroppings, and a view of Cheshire and its long lake. This trail ties to the Appalacian Trail, so you can, if you want, walk forever!


  • A few swimming places nearby are Winsor Pond (more secluded) and the Cheshire Reservoir (Hoosac Lake). There are many other places as well; Onota Lake and Silver Lake (Pittsfield), Pontoosuc Lake (Lanesboro).


  • There is a nearby bike trail, Ashuwillticook Rail Trail, that goes through Cheshire and Adams. This same trail goes by Cheshire Lake.

Water rafting/ canoeing/ kayaking

  • Kayaking on Windsor Pond is beautiful. If you are looking for kayak rental, there is Zoar Outdoor in Charlemont. 413-339-4010

Orchards/ farms

  • Lakeview Orchards, (413) 448-6009 in Lanesboro
  • Green River Farms, (413) 458-2470 in Williamstown
  • Cricket Creek Farm, (413) 458-5888 in Williamstown
  • Holiday Farm, (413) 684-2470 in Dalton


  • Downhill skiing: 20 miles to Jiminy Peak, 35 miles to Mt Snow, 48 miles to Stratton. Cross country skiing: 9 miles to Prospect Mountain, 12 miles to Taconic Trail, 21 miles to Mt Greylock, 32 miles to Pineridge, and 37 miles to Notchview. Tubing: 20 miles to Snowy Owl. Snowmobile tours: 17 miles to Twin Brooks.


  • Mass MOCA, Berkshire Museum, Clark Art Institute, Norman Rockwell Museum, Crane Museum, Williams College Museum,

Local Venues

  • Hancock Shaker Village: 32 miles, Tnaglewood Music Center: 35 miles, Norman Rockwell Museum: 43 miles, Jacob’s Pillow Dance Festival: 47 miles

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