Insiders Guide to the Berkshires

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The colonial towns along Route 7 in western Massachusetts are quintessential New England any time of year. Summer festivals bring out cultural crowds, while late September swarms with leaf-peepers.

Here’s a guide to this American classic, no matter when you visit:

> Where to Eat:

Here, it’s all about the Berkshire farmer—not to mention the cheese-monger, butcher, distiller, and brewer. Chefs source locally at Gramercy Bistro, at the Massachusetts Museum of Contemporary Art in North Adams, and at Williamstown spots.

Mezze Bistro + Bar draws loyal fans to its bucolic farm setting for small plates with a Moroccan-Greek pedigree, and Hops & Vines has oysters, craft beer, and a fireplace—a welcome sight after a day on the road.

> Where to Stay:

In continuous operation since the 18th century, Stockbridge‘s Red Lion Inn remains a classic, with rocking chairs on the porch and doilies and canopy beds in the rooms.

On the other end of the Stockbridge spectrum, the lakefront Kripalu Center for Yoga & Health hosts retreats with a labyrinth, yoga and dance classes, and tai chi on the lawn.

The Williamstown Bed & Breakfast is a five-minute walk from Williams College campus happenings. Outside Lenox, the ultraluxe Blantyre dates to 1901 and was modeled after a Scottish castle.

> When to Go: 

The summer home of the Boston Symphony Orchestra, Tanglewood in Lenox provides a cultured sound track for picnics on the grass and seats in the historic shed.

Jacob’s Pillow in Becket is the nation’s leading summer dance festival (and its longest running). Film and TV talent come to do the standards at the Tony Award–winning
 Williamstown Theatre Festival each summer. Dozens of their productions have transferred to Broadway.

In late October, the Williamstown Film Festival convenes the likes of Sigourney Weaver and Joanne Woodward. The Barrington Stage Company’s Musical Theatre Lab in Pittsfield premieres works from May to August. The one-act musical comedy The 25th Annual Putnam County Spelling Bee started at this theater.

> What to Read:

In Ethan Frome (1911), Edith Wharton makes the winter landscape of Berkshire County a major character in a page-turner about adultery, set during a blizzard in a fictional town inspired by Lenox. Liam Neeson starred in the 1993 film.

While Henry David Thoreau was at Walden Pond, he wrote about a solo hike up Mount Greylock in a passage of A Week on the Concord and Merrimack Rivers (1849). The account inspires an annual summer climb for Thoreau fans.

> Literary Tour: Berkshire Bards

Quiet beauty here has incubated centuries of literature. Edith Wharton wrote The House of Mirth (1905) at the Mount, her Lenox estate popular for its Italian formal garden and ghost tours.

In Cummington, poet William Cullen Bryant’s homestead offers guided tours.

Nathaniel Hawthorne’s “little red house,” where he wrote The House of the Seven Gables (1851), has been rebuilt behind Tanglewood.

In Pittsfield, Herman Melville penned Moby Dick (1851) from his study at Arrowhead, which looks out onto Mount Greylock.

> Travel Trivia: 

  • Every U.S. dollar is printed on cotton-based paper from Crane and Company, a Berkshires producer that’s been the sole supplier to the Treasury since 1879.
  • North America’s earliest recorded reference to baseball appeared in a Pittsfield bylaw dated 1791.
  • Oscar winner Gwyneth Paltrow made her acting debut at the Williamstown Theatre Festival in 1981.

This piece originally appeared in the February/March 2014 issue of National Geographic Traveler magazine.

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