Northern Berkshires, MA

From Poughkeepsie: 2 hours

While the Berkshires are renowned for their unparalleled fall-foliage displays (especially in the northern half), the region is also host to a number of cultural attractions worthy of inclusion on your itinerary — not just as “Plan B” indoor activities when Mother Nature isn’t cooperating. After a 130,000 sq ft expansion in May, the Massachusetts Museum of Contemporary Art — lovingly known as Mass MoCA — is now the largest contemporary-art museum in the nation. Housed in an interconnecting series of former factory buildings, the museum presents exhibits and installations of oversize, immersive, and otherwise avant-garde visual art, as well as a robust roster of performing arts in dance, music, film, and theater. In neighboring Williamstown, the Clark Art Institute recently completed its own $145 million expansion. The museum’s eclectic collections include European and American visual and decorative art from the Renaissance to the early 20th century, featuring French Impressionist paintings (with more than 30 by Renoir), fine British and American silver, photography, and sculpture.

(L to R) Mass MoCA; Clark Art Institute

- Advertisement -

Around the corner, the Williams College Museum of Art presents more than 14,000 works, most notably Native American, Egyptian, Greco-Roman, and Assyrian art. When you’re ready for some fresh air, drive to the top of Mount Greylock. At 3,491 feet, its summit is the highest point in Massachusetts, offering breathtaking views of five states, along with myriad walking, hiking, horse, and biking trails. Before leaving the summit, be sure to duck into Bascom Lodge for a coffee or a hot cider, and sit in front of a roaring fire to take the chill off. Back in North Adams, take a fun side trip to Natural Bridge State Park, site of the only natural marble bridge/arch in North America.

STAY: Porches Inn

Located directly across the street from Mass MoCA in North Adams, this boutique inn personifies funky. Spanning a series of beautifully restored 19th-century Victorian row houses that used to shelter factory workers during the town’s industrial heyday, Porches delivers lots of comfort with a shabby-chic vibe. Its rooms and bi-level suites offer colorful, whimsical décor, plus touches like Apple TVs, stocked mini-bars, and Jacuzzis. Some have lofts and spiral staircases, while others have private porches and kitchens. In the fall, the Inn’s heated pool, heated stone patio, and bonfire pit are especially welcome amenities, while its farm-to-table continental breakfast is a great way to start the day. From $299/night;

Our Westchester Home Design Awards event is June 26!

Our Wine & Food Festival returns June 4-9!

Our Wunderkinds event takes place on May 23!

Our Best of Business Ballot is open through May 15!

Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

Our Best of Westchester Elimination Ballot is open through March 6!

Holiday flash sale ... subscribe and save 50%

Limited time offer. New subscribers only.