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Berkshires towns homepages

How to get to the Berkshires

Here are inks for local and regional public transportation depots and stops, plus where to get Peter Pan bus and Amtrak train schedules and tickets: how to get to the Berkshires.

Cheshire, Mass

The Berkshires town of Cheshire, Mass. boasts a 500 acre lake, spectacular views from Stafford Hill, and one of the most unusual monuments anywhere, which celebrates the 1,235 pound cheese presented to President Jefferson by Cheshire farmers. Cheshire is located within the valley of the Hoosic River, and is the site of a dammed reservoir on the river. To the west, parts of Mount Greylock State Reservation take up sections of town, and includes a section of the auto road.

To the southeast, North Mountain peaks just outside town limits before descending to the valley. The Appalachian Trail crosses through the center of town, heading from North Mountain to Mount Greylock. The southern foothils of the Hoosac Range make up much of the eastern side of town, and much of the land is dotted with sections of the Chalet and Stafford Hill Wildlife Management Areas. Several other brooks feed into the river along the way.

“The Great Cheese symbolized Cheshire’s satisfaction with the election of Thomas Jefferson to the Presidency in 1800. The idea of creating this monster among edibles was put forth by a baptist clergyman of Cheshire, Elder John Leland. A friend of Jefferson, he thought the town should send the new executive a testimonial of esteem.” (The Berkshire Hills, by Federal Writers’ Project, © 1939, Berkshire Hills Conference, Inc.)

The popular Ashuwillticook Rail Trail runs along the shore of Cheshire reservoir, and many Appalachian Trail through-hikers receive mail and provisions at the village post office.

Cheshire, MA facts:

  • Town Hall: 80 Church St.
  • Phone: (413)743-1690
  • Population: 3,401
  • Settled/Inc’d: 1766
  • Named for: Cheshire, England
  • Elevation: 945′
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