When warm weather sets in, performing artists from New York, Boston and the rest of the world find their way to the Berkshires, where the life of the mind flourishes among the rolling, wooded hills of western Massachusetts.

The Tanglewood Music Festival is the Berkshires’ pre-eminent event. The summer home of the Boston Symphony Orchestra, Tanglewood attracts top-flight artists from around the globe, who perform works in a wide variety of genres. The lush 500-acre estate encompasses four lovely performance venues with plenty of seating, but Tanglewood’s calling card is a glamorous picnic dinner. Some music lovers spread out blankets and gourmet meals on The Lawn, dining by candlelight, sometimes with china, silver and crystal. Others bring the children and tuna sandwiches.

The Tanglewood Music Festival

The season culminates in early September with the annual Tanglewood Jazz Festival. The internationally acclaimed Jacob’s Pillow Dance Festival offers dance performances, lectures, demonstrations, films and live music. ‘The Pillow’, a long-time haunt of the legendary Martha Graham, is famed for encouraging the dance world’s rising stars. You can enjoy ballet one night and hip-hop, modern jazz or Spanish flamenco the next. Close to Lenox in the small town of Becket, the 161-acre property, a National Historic Landmark, is home to multiple performance spaces, a dance school and carefully preserved wetlands that can be enjoyed on a self-guided tour of the grounds.

Shakespeare & Company’s focus is—not surprisingly—on the Bard, but its three performance spaces also schedule contemporary works and revivals. The celebrated actor-training programme gives the company an energy that makes it as irresistible to established stars as talented unknowns. Literature is another art closely associated with the Berkshires. The Mount was the home of novelist Edith Wharton from 1902 to 1911. Wharton claimed to be “a better landscape gardener than novelist”—the judges who made her the first woman to win the Pulitzer Prize for fiction might disagree—and the Mount preserves her legacy.

The venerable Berkshire Theatre Festival in Stockbridge presents revivals of plays and musicals, as well as original productions. Top-notch actors, directors, set designers and playwrights make and build on their reputations on the festival’s two stages. The company makes its home in the 1888 Stockbridge Casino, designed by Stanford White. In another part of this tiny town is the Norman Rockwell Museum, home to the world’s largest collection of works by the beloved 20th-century American artist. The iconic Four Freedoms and numerous Saturday Evening Post covers form the heart of the collection of more than 500 paintings and drawings by Rockwell, who lived in Stockbridge for the last 25 years of his life (he died in 1978).

Anchoring Stockbridge’s Rockwell-perfect Main Street is the friendly Red Lion Inn, a landmark since the late 1700s. The inn offers a variety of accommodation, some with shared baths and some in houses adjoining the main building. There’s even a guest room in an 1899 firehouse down the block.
 

 
 

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