Arts and Culture Weekend Getaway in the Berkshire Mountains

  • Distance from New York City: 169 miles
  • Best time: May to November
  • Best for: Girl's GetawayArts and CultureFood and Wine

It's little wonder culture hounds makes their way to western Massachusetts each summer. The hamlets nestled in the Berkshire Mountains are blessed with terrific art, music, theater, and antiquing. Here, eight museums join renowned stage productions and dance festivals, plus a little music venue called Tanglewood. All that, plus a gorgeous natural setting of mountains and meadows—accessible on foot, bike, raft, balloon, horse, or even llama—is enough to uplift spirits. And there's no shortage of spas here, in the event you need extra help working out the kinks. – By Lisa Oppenheimer


The Berkshire Mountains Cheat Sheet

View a printable list of all sights, restaurants, entertainment, and hotels from this itinerary. View

1 Get your bearings by venturing into Downtown Lenox. Poke your head in and around the shops and galleries located along the main thoroughfares of Main, Franklin, Church, and West streets.

2 Enjoy a lovely dinner in the outdoor courtyard of Cafe Lucia, a Berkshires favorite that's been dishing up Italian specialties based on local ingredients for the last three decades.

3 In season, there's nothing more soothing than al fresco entertainment on the historic grounds of Tanglewood. (Even with no show on, it's still worth visiting to experience the setting.) Classical greats perform at the Koussevitzky Shed, while smaller shows go on at the newer Ozawa Hall. Economical lawn seats are almost always available on the fly, except during big events such as James Taylor nights. Picnics are not only welcomed, they're encouraged; locals haul in all manner of décor, including tables and candelabras. Stake out a stretch of grass and enjoy.


1 Eggs with roasted potatoes or croissant French toast will get your day off to a perfectly glorious start at Haven in downtown Lenox.

2 Just a few minutes outside of town, the thoroughly modern spa at the historic Cranwell estate has all the wraps, massages, and treatments to turn you to mush—in a good way. For true bliss, go for the full Mosaic "envelopment."

3 Those who can't afford a room at the glorious Wheatleigh Hotel—which, let's face it, is most of us—can be consoled with a lunch of gnocchi, lamb loin, and salmon tartar at the Italian villa's splendid Library restaurant. The view is just as tasty. Reservations are strongly recommended.

4 Leave Lenox behind for Williamstown, a quick, less-than-30-mile drive north on US 7. Here, The Clark Art Institute may be small compared to some of its urban brethren, but it's stunning for its collection that includes Monet, Renoir, and Degas, among other masters.

5 Retrace your drive south to reach Stockbridge, just past Lenox, to explore the charming outdoor gardens at Chesterwood. Its studio was the artistic home of Daniel Chester French, most famous for sculpting the Lincoln Memorial.

6 Wend your way further south to Great Barrington for a stellar pre-show dinner at Café Adam. Named for its chef, Adam Zieminski, the small eatery gets raves for its regional ingredients and eclectic menu, ranging from fresh farm burgers and hand-cut fries to divine pastas made on the premises. Reservations are a must.

7Cap off your night with a performance at Great Barrington's century-old Mahaiwe Performing Arts Center, an art house that hosts year-round productions (unlike many of its Berkshire stage siblings). Guest performers include the likes of Betty Buckley and Barbara Cook, with fare ranging from opera and classic films to dance and playful musical sing-alongs.


1 Lenox's modest Spoon has a surprisingly wide-ranging breakfast menu that features everything from omelets and toast to crab cakes and eggs with aioli. Breakfast is served all day, too.

2 Also in Lenox, Edith Wharton's one-time estate, The Mount, has lived almost as dramatic a life as her characters in recent years. It was restored after a closure scare a few years back, but you can still enjoy the dignified manor, including its gardens, living areas, and exhibits beginning in the middle of May.

3 A trip to the Berkshires isn't complete without a visit to the Norman Rockwell Museum in Stockbridge. Enjoy the famed paintings, humor, and cover art from the American master and then grab a giant sandwich or some chowder at the tchotchke-filled Widow Bingham's Tavern at the Red Lion Inn before heading back to New York City.

Where to Stay

Harking back to a bygone era, the stately mansion Cranwell (rooms from $199/night) got its start about 100 years ago as a getaway for the era's wealthy. Take your choice of restored rooms in the main mansion or in any of the luxurious cottages sprinkled about the rolling grounds.

The adorable Shaker Mill Inn (rooms from $109/night) earns points for its lovely rooms and its charming innkeepers. The slightly off-the-beaten-path location (though still only a few short minutes to Tanglewood) also offers good value relative to some of its more centrally located brethren.

Filled with tchotchkes and standing on the site of an old stagecoach stop, the historic Red Lion Inn (rooms from $140/night) gives the impression of a place lovingly frozen in time. The pedigreed grand dame nevertheless manages to offer some modern touches, like an outdoor pool with a heated deck that stays warm all winter long.

When to Go

Certainly, summer is when the Berkshires really shines—when the notes of the Boston Symphony Opera float out of Tanglewood, Jacobs Pillow is alive with dance, and the Williamstown Theatre Festival and other stage companies lift their curtains. If you can get tickets, the Fourth of July at the Tanglewood shed (usually with James Taylor) is an experience to behold. For a full calendar of events, visit

Many museums and several acclaimed companies—including the highly regarded Mahaiwe Performing Arts Center—stay open year round, making the money-saving shoulder seasons (particularly the area's lovely autumn months) excellent times to visit.

Wintertime is typically for those looking for spa experiences or cross-country and downhill skiing. Christmas in Stockbridge—when the town recreates in perfect detail a scene from a Norman Rockwell painting—is a quaint tradition that's worth a visit.

How to Get There

There are other forms of transportation (including public busses, trains, and taxis), but a car here is really a must.

By Car from Boston: The Berkshires are roughly three hours from Boston, due west on the Massachusetts Turnpike. Exit 2 will get you into Lee and Exit 1 into Stockbridge.

By Car from New York City: From NYC, the Berkshires are about three and a half hours north. Take I-87 toward Albany and then I-90 East (the Massachusetts Turnpike). Take Exit 1 for Stockbridge and Exit 2 for Lee.

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