17 Best Sights in The Berkshires, Massachusetts

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 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 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.

The collection at this fine museum (moving to a new home in 2027) spans a range of eras and cultures, with American and 20th-century art as two major focuses. Get an inside look at Williams students' experience with Object Lab, a hybrid gallery-classroom curated by faculty to coincide with students' studies.

This charming museum traces the career of one of America's most beloved illustrators, beginning with his first Saturday Evening Post cover in 1916. The crown jewel of the 570 Rockwell illustrations is the famed Four Freedoms gallery, although various works—including his Post covers and self-portraits—are equally charming. The museum also mounts exhibits of work by other artists. Rockwell's studio was moved to the museum grounds and is complete in every detail. Stroll the 36-acre site, picnic on the grounds, or relax at the outdoor café (late May–mid-October). There's a children's version of the audio tour and a scavenger hunt.

Passing through the Hoosac River Valley, the paved 12.7-mile Ashuwillticook (pronounced Ash-oo-will-ti-cook) trail links Adams with Pittsfield. The trail follows an old railroad, passing through rugged woodland and alongside Cheshire Reservoir. Walkers, joggers, cyclists, in-line skaters, and cross-country skiers all enjoy this route.

This rock garden beside the Housatonic River (the Native American name means "river beyond the mountains") is a National Natural Landmark, with 5 miles of hiking trails passing through fields of wildflowers. The 277-acre site has a visitor center and a museum, as well as the state's largest cottonwood trees.

The smell of freshly baked cider doughnuts greets you upon entering this orchard's market, which also sells cider and maple syrup. Seasonally you'll find many apple varieties bagged for purchase, but it's more fun to head into the orchard and pick your own.

Opened in 1903, this "universal" museum has a little bit of everything: paintings from the Hudson River School, local artifacts, and natural history specimens both animal and mineral. The Hall of Innovation showcases Berkshires innovators whose creations range from special effects for Star Wars to the paper used for U.S. currency. Don't miss the Egyptian mummy, or the aquarium with a touch tank in the basement.

In a restored 1903 railroad station, the museum's collection includes antique rail equipment, vintage items, a children's area, and a large working model railway. Short rides aboard the Lenox Jitney train from one end of the grounds to the other are available. 

From late June through September, this public-arts project presents visual and performing arts events including exhibitions, video screenings, site-specific installations, and opening galas and performances.

America's third Shaker community, Hancock was founded in the 1790s. At its peak in the 1840s, the village had almost 300 inhabitants who made their living farming, selling seeds and herbs, making medicines, and producing crafts. The religious community officially closed in 1960, but visitors today can still see demonstrations of blacksmithing, woodworking, and more. Many examples of Shaker ingenuity are on display: the Round Stone Barn and the Laundry and Machine Shop are two of the most interesting buildings. The Shaker focus on sustainability has been maintained in the form of water turbines, sustainable gardens, and a solar array. There's also a farm (with a wonderful barn), some period gardens, a museum shop with reproduction Shaker furniture, a picnic area, and a café. Visit in April to catch the baby animals at the farm, or in September for the country fair. Reserve early if you want a spot at the Shaker-inspired suppers in October.

Bring the kids to this 600-acre farm whose family-friendly activities include games and tractor rides. Seasonal offerings range from pick-your-own pumpkins (mid-September–October) to cut-your-own Christmas trees (late November–late December) and a petting farm from late June through August. For a real treat, catch a weekend brunch (late February–early April) with homemade maple syrup atop pancakes, waffles, and French toast.

For great views with minimal effort, hike Monument Mountain, famous as a spot for literary inspiration. Nathaniel Hawthorne and Herman Melville trekked it on August 5, 1850, seeking shelter in a cave during a thunderstorm. There they discussed ideas that would become part of a novel called Moby-Dick. While poet William Cullen Bryant stayed in the area, he penned a lyrical poem, "Monument Mountain," about a lovesick Mohican maiden who jumped to her death from the cliffs. Most hikers find the 2½-mile loop an easy stroll.

Beaver ponds, hardwood forests, and sun-dappled meadows abound at this preserve run by the Massachusetts Audubon Society. Recent wildlife sightings are noted on whiteboards at the entrance and the visitor center, so you'll know what to watch for on the 7 miles of trails. These include loops that range in difficulty from a half-hour stroll around a pond to a three-hour mountain hike. Trails are also open in winter for snowshoeing. At the visitor center there's a nature play area for children.

Raspberries ripen here early July–August, and you can pick your own pumpkins September and October. Grab a roast turkey (or other) sandwich, served on freshly baked bread, for a fine homemade lunch. If you have time to linger, check out the small turtle pond in the plant nursery, and see the animal area replete with goats, chickens, llamas, and more.

In addition to offering pick-your-own blueberries, tomatoes, and pumpkins on a seasonal basis, Whitney's sells fresh produce, herbs, and dairy products. A deli and a bakery are also on-site, as well as an outdoor playground and greenhouse.