It would be inaccurate to call the Berkshires—the rural, mountainous region of western Massachusetts—an undiscovered vacation spot. After all, the Berkshires has been a popular summer hideaway for well-heeled New Yorkers and Bostonians since the mid-19th century, when city folk flocked to the area in the summer for its restorative mountain breezes and natural springs. But compared to Massachusetts's other tourist hotspots (Boston, Cape Cod, Martha's Vineyard, and Nantucket), the Berkshires has a lower, softer profile: It's well-known regionally, but it's not a marquee resort destination.
The Berkshires's appeal chiefly lies in its juxtaposition of sophistication and rusticity. In the course of a day, it's possible to hike the state's tallest peak, view world-class art, dine at restaurants that rival any of Manhattan or Boston's best, and take in a performance featuring stars of music, dance, film, television, and/or Broadway. But why jam it all into one day when you don't have to? The Berkshires, after all, is a place for rest and relaxation, as well as recreation.
When people say, "the Berkshires," they're actually referring to a few separate but intertwined entities. First, there is Berkshire County, the westernmost county in Massachusetts, which encompasses 32 towns as it runs along the New York border from Connecticut to Vermont. The name also refers to the area's defining geologic feature—the Berkshire Mountains—actually the southern continuation of Vermont's Green Mountains. Primarily though, when people say "the Berkshires," they are describing an area bound by its high concentration of cultural, historical, and recreational activities.
"You could spend a week in the Berkshires and still not see all there is to see," says Barbara Dowling, curator of Naumkeag, the historic house and garden in Stockbridge, Massachusetts.
She's not wrong, but I had to start somewhere.
North Adams And Williamstown
After renting a car (chip in the extra few bucks for a GPS), I decided to wend my way through the Berkshires from north to south starting with the neighboring townships of North Adams and Williamstown. Both are college towns. (Williamstown is home to Williams College, and North Adams has the Massachusetts College of Liberal Arts.) Both lie in the shadow of Mt. Greylock, the state's highest peak at 3,491 feet. And both are home to world-class art institutions. But Williamstown is genteel to North Adams's funky, blue-collar casualness.
What to See: First stop in North Adams has to be MASS MoCA (Massachusetts Museum of Contemporary Art, 87 Marshall St., 413-662-2111, massmoca.org). Housed in a complex of restored factory buildings in downtown North Adams, it is the nation's largest center devoted to contemporary art: 110,000 square feet of gallery space, with a single gallery running the length of a football field; an outdoor cinema with a 50-foot-wide movie screen and a 70-millimeter projector; and two performance courtyards, one of which spans 22,500 square feet. In all, the campus spans 13 acres—or about one-third—of North Adams's downtown. On the walls this summer is Badlands: New Horizons in Landscape, a mixed media exhibit looking at land usage, environmental politics, and the relativity of aesthetic beauty.
Just 15 minutes west on Route 2, Williamstown boasts its own first-class art museums: The Sterling and Francine Clark Art Institute (225 South St., 413-458-2303, clarkart.edu) and The Williams College Museum of Art (15 Lawrence Hall Dr., Suite 2, 413-597-2429, wcma.org). Unlike Mass MoCA, these museums devote much of their gallery space to established masters rather than up-and-coming provocateurs.
The Clark opened in 1955 and is named for Singer sewing-machine heir, Robert Sterling, and his wife, Francine. Originally, the museum was built to house their extensive collection of French Impressionist art. But in the decades since, the museum has acquired impressive holdings of American and European paintings, drawings, sculpture, and photography. The museum is also renowned for its collections of English silver and decorative arts and its world-class art-history library, which is open to the public.
Smaller in scale, but no less impressive is The Williams College Museum of Art. The WCMA is home to 5,500 works in the American collection alone, including pieces by Winslow Homer, Georgia O'Keeffe, and Edward Hopper, as well as ever-expanding collections of antiquities and African art.
Sure, the galleries are inspiring, but the best views in the Berkshires will always be of the Berkshires. And there is no better vantage point than the summit of Mt. Greylock. Part of the 12,500-acre Mt. Greylock State Reservation, the state's highest peak provides 90-mile views in all directions. Because of road repairs, the summit is not accessible by car until 2009, but the hiking and mountain biking trails, which form a section of the Appalachian Trail, remain open. The best points of access are Greylock Glen in Adams or Haley Farm in Williamstown.
No trip to the Berkshires in summer would be complete without a visit to the Williamstown Theatre Festival (62 Center for Theatre and Dance of Williams College, 1000 Main St., wtfestival.org). Broadway and Hollywood converge in the Berkshires for this summer-long festival. Performances this year include Anton Chekhov's Three Sisters and a revival of the rom-com musical She Loves Me. Stars already confirmed include Kate Burton of Grey's Anatomy, SNL's Darrell Hammond, and Ed's Tom Cavanagh.
Where to Sleep: For an exceptional experience, book a stay at The Porches Inn at MASS MoCA (231 River St., 413-664-0400, porches.com) in North Adams. Located across the street from the museum in renovated Victorian row houses, the Porches is a perfect blend of quaint charm and modern convenience. There are beadboard walls and ornately carved banisters, but also free wi-fi, a year-round outdoor heated lap pool, and sumptuous continental breakfast.
Where to Shop: Stroll through downtown North Adams. Stores like Persnickety Toys (13 Eagle St., 413-662-2990) reveal the hip quotient in this working-class town. In preppy Williamstown, nearly all the shopping is contained on Spring Street, where you'll find furniture, rare books, and more at Library Antiques (70 Spring St., 413-458-3436,libraryantiques.com) and unexpected gift items at Where'd You Get That!? (100 Spring St., 413-458-2206, wygt.com).
Pittsfield, the government seat of Berkshire County, lies south of Williamstown and has been enjoying a renewed vibrancy downtown.
What to See: The Colonial Theatre (111 South St., 413-997-4444, thecolonialtheatre.org), a recently renovated 1903 vaudeville theater, now hosts national touring productions and concerts.
The Berkshire Museum (39 South St., 413-443-7171, berkshiremuseum.org) is a must-stop for families traveling with curious little ones. A mixture of natural science, local history, and art, the museum includes an aquarium, a dinosaur and paleontology gallery, exhibits featuring works by Norman Rockwell and Hudson River School painters, and a gallery of Alexander Calder-designed toys, including replicas kids can actually play with.
Also worth a visit is Arrowhead (780 Holmes Rd., 413-442-1793, mobydick.org), Herman Melville's one-time farm located just outside of the downtown. Melville lived here from 1850-1863, during which time he wrote Moby Dick and several other works. The house is a registered National Historic Landmark, and tours are available from Memorial Day to Columbus Day.
Just west of Pittsfield, in the tiny hamlet of Hancock, lies Hancock Shaker Village (34 Lebanon Mountain Rd., 413-443-0188, hancockshakervillage.org). Here you can experience the grace and simplicity of the Shakers on 1,200-acres of pasture, forest, and farmland with 20 restored, authentic Shaker buildings.
Lenox And Stockbridge
These two towns form the cultural nexus of the southern Berkshires. Lenox still feels like the Gilded Age-era resort town it was in those heady pre-federal income tax years. Stockbridge also has its share of Gilded Age "summer cottages" but simultaneously keeps much of its Colonial New England charm. In fact, so adorably quaint is the village that Norman Rockwell—a resident of the town from 1953 until his death in 1978—chose to immortalize its all-American hominess in many of his most famous paintings, including Stockbridge Main Street at Christmas.
What to See: Author Edith Wharton was one of the Gilded Age New Yorkers who took up residence in the Berkshires. The Mount (2 Plunkett St., 413-551-5111, edithwharton.org), the beloved summer estate that she designed and decorated herself, still stands and, after extensive renovation work, is open to the public. Unfortunately, The Mount is experiencing financial difficulties, so go this year, because its future is uncertain.
Just north of The Mount is Shakespeare & Co. (70 Kemble St., 413-637-1199, shakespeare.org), a theater company specializing in Shakespearean productions as well as more contemporary playwrights. Aside from its busy production schedule, Shakespeare & Co. hosts actors' workshops that have attracted A-listers like Sigourney Weaver, Keanu Reeves, and Andie MacDowell.
Located in nearby Beckett, Massachusetts, Jacob's Pillow (358 George Carter Rd., 413-243-9919, jacobspillow.org) is the nation's first and longest running dance festival. It's celebrating its 76th year with a full summer slate of performances, classes, lectures, book signings, and exhibits.
Arguably the center of the Berkshire's cultural universe is Tanglewood (297 West St., 413-637-1600, bso.org). Every summer, for three glorious months, the Boston Symphony Orchestra relocates to the sweeping lawns and shaded groves of Tanglewood's campus. Led by maestro James Levine, the BSO (well, the other BSO) will tackle a program of Mozart, Beethoven, Schubert, and Brahms this summer. Plus, the BSO will cede the stage some nights to luminaries like Yo-Yo Ma, Joshua Bell, James Taylor, and Garrison Keillor, who will broadcast a live edition of A Prairie Home Companion from Tanglewood on June 28.
The man who celebrated his affection for the Berkshires and its inhabitants in some of the country's most beloved images is now the subject of much celebration himself. The Norman Rockwell Museum (9 Glendale Rd., Rte. 183, 413-298-4100, nrm.org) contains the largest collection of Rockwell's work—including his 323 The Saturday Evening Post covers—in the world. Also onsite is Rockwell's studio.
Another historic home worth a visit is Naumkeag (5 Prospect Hill Rd., 413-298-8146), the summer residence of Joseph Hodges Choate, who was the U.S. ambassador to Great Britain from 1899-1905. The home is a blend of Norman castle and Gilded Age seaside cottage designed by noted Beaux-Arts architectural firm McKim, Mead & White. Perched above Stockbridge's village center, the estate's grounds, designed by celebrated landscape architect Fletcher Steele, offer beautiful views.
You also don't want to miss the Berkshire Theatre Festival (413-298-5576, berkshiretheatre.org), which is celebrating its 80th season this year with plays by Harold Pinter, Noël Coward, and Robert Bolt.
Where to Stay: In general, there is no shortage of bed and breakfasts in the Berkshires, and nowhere is that more true than in Lenox and Stockbridge.
The Inn at Stockbridge (30 East St., 888-466-7865, stockbridgeinn.com) is the essence of Berkshire hospitality. Innkeepers Alice and Len Schiller keep the vibe welcoming and homespun, with nightly cocktail hours and a freshly prepared full breakfast every morning, where you'll likely be greeted by their seven-year-old standard poodle, Mia.
The venerable Red Lion Inn (30 Main St., 413-298-5545, redlioninn.com) is a Stockbridge landmark, providing lodging to weary travelers since the late 1700s. Originally just eight rooms, the inn, with its rocking chair-strewn wide front porch, now boasts more than 100 individually decorated rooms in its main house, including extra suites and guest houses. Its restaurants (an elegant Main Dining Room, the cozy Widow Bingham's Tavern, the casual Lion's Den pub, and, in warmer months, the verdant Courtyard) draw patrons from all over the area, hungry for the inn's ever-changing menu of New American cuisine.
For those who want to splurge, Canyon Ranch (165 Kemble St., 413-637-4100, canyonranch.com) in Lenox is the way to go. Located on 120 lush acres, Canyon Ranch is a full-service spa/resort. Its sprawling campus of buildings, connected by climate-controlled, glass-enclosed walkways (yes, you can walk outside, too), is highlighted by the renovated Bellefontaine mansion, built in 1897 as a replica of Le Petit Trianon, Louis XV's Versailles chateau. The list of amenities and services is epic, ranging from a hair salon to kayaking expeditions.