9 Best Sights in The Berkshires, Massachusetts

The gardens' 15 acres contain extensive plantings of exotic and native flora—some 2,500 varieties in all—plus greenhouses, ponds, nature trails, and a small gallery. A guided tour, included with admission, leaves daily at 11 am, or grab a self-guided tour at your leisure. October's Harvest Festival is by far the biggest of the facility's annual events.

The sweet scent of the country's premier craft gin permeates the Berkshires' first legal distillery since Prohibition. The retail store, open every afternoon, sells Greylock Gin, a multiple gold-medal winner, and Ethereal Gin, whose ingredients are reimagined every season, among other spirits. Take a self-guided distillery tour and try a complimentary tasting. During the summer, there's live music in the outdoor pavilion where you can sip on craft cocktails. 

One of the nation's notable small art museums, the Clark has won numerous architectural awards for its 2014 redesign by Reed Hilderbrand and for the new Clark Center by Pritzker Prize–winning architect Tadao Ando. The polished concrete of the latter visually connects it to the landscape through glass windows and open spaces. The museum has a large collection of Impressionist works, in particular many significant Renoir paintings. Other strengths include English silver, European and American photography 1840–1920, and 17th- and 18th-century Flemish and Dutch masterworks.

For 10 weeks every summer, the tiny town of Becket, 14 miles southeast of Lenox, becomes a hub of the dance world. The Jacob's Pillow Dance Festival showcases world-renowned performers of ballet, modern, and international dance. Before the main events, works in progress and even some of the final productions are staged outdoors, often free of charge.

Formerly the home of the Sprague Electrical Company, the nation's largest center for contemporary visual and performing arts is one of the finest such facilities in the world, a major draw for its art shows, large music festivals, dance presentations, and film screenings. Expansion in 2017 nearly doubled the amount of gallery space, bringing the total to a quarter million square feet, which includes the wall drawings of Sol LeWitt, an immersive light-based exhibit by James Turrell, and a large room in the main gallery that allows for massive exhibits that wouldn't fit anywhere else. A Kidspace, studios, cafés, shops, and festivals and other special events round out the offerings.

The Berkshire cottage of Joseph Choate (1832–1917), an influential New York City lawyer and the ambassador to Great Britain during President William McKinley's administration, provides a glimpse into the Gilded Age lifestyle. The 44-room gabled mansion, designed by Stanford White and completed in 1887, sits atop Prospect Hill. Its many original furnishings and artworks span three centuries; the collection of Chinese porcelain is particularly noteworthy. The meticulously kept 8 acres of formal gardens, a three-decade project of Choate's daughter, Mabel, and landscape designer Fletcher Steele, alone make this site worth a visit. Creative use of the property now includes a Winter Lights display, with over 200,000 twinkling LED lights; a Halloween-inspired pumpkin trail and haunted house; live music nights with picnics; and a springtime Daffodil Festival.

Jim Schantz's gallery is small and tucked behind a bank, but it displays some of the finest glasswork in the world. With items from nearly five dozen contemporary artists—including Dale Chihuly and Lino Tagliapietra—the museum-quality collection is truly stunning. Call ahead because hours are limited during the winter.

This 1902 mansion with myriad classical influences was the summer home of novelist Edith Wharton. The 42-room house and 3 acres of formal gardens were designed by Wharton, who is considered by many to have set the standard for 20th-century interior decoration. In designing the Mount, she followed the principles set forth in her book The Decoration of Houses (1897), creating a calm and well-ordered home. To date, nearly $15 million has been spent on an ongoing restoration project. Summer is a fine time to enjoy the informal café and occasional free concerts on the terrace. Guided tours take place during regular hours, the private "ghost tour" after hours, and noteworthy authors make regular visits to discuss their latest books.

The collection at this fine museum spans a range of eras and cultures, with American and 20th-century art as two major focuses. The original octagonal structure facing Main Street was built as a library in 1846, and the painted wall above the stairs is by Sol LeWitt—actually the third mural to occupy the wall. Special events take place on the outdoor patio on Thursday night in summer. Get an inside look at Williams students' experience with Object Lab, a hybrid gallery-classroom curated by faculty to coincide with students' studies.