How to Plan an Art-Filled Day Trip to the Berkshires

For those willing to venture further afield from New York City than the Hudson Valley or Long Island, there’s a wealth of cultural sites to explore in the Berkshires. This mountainous stretch of western Massachusetts is a popular destination for leaf-peepers in the fall. But don’t sleep on the region during the summer, when outdoor festivals, performances, and events supplement the year-round offering of museums, galleries, and areas of natural beauty. 

The area’s cultural linchpin is MASS MoCA, a vast art museum housed within a complex of former warehouses and textile factory buildings between two branches of the Hoosic River. Situated in the town of North Adams, which is a hub for independent artists and galleries, the 250,000-square-foot museum is one of the country’s largest dedicated to contemporary art. Its permanent collection features an impressive collection of Sol Lewitt’s Wall Drawings, a long-standing exhibition of sculptures by Anselm Kiefer, various marble works by Louise Bourgeois, and James Turrell’s largest free-standing circular Skyspace, titled C.A.V.U.

Current exhibitions include a Vincent Valdez retrospective, “Just a Dream…”, the American artist’s first major museum survey spanning two decades of work, and the first-phase manifestation of Alison Pebworth’s “Cultural Apothecary” inspired by a 19th-century neurological disorder called Americanitis. Meanwhile, an immersive installation by Jeffrey Gibson that follows his U.S. representation at the 60th Venice Biennale will culminate in a dance party on August 30, hosted with multimedia performance artist MX Oops.

At the end of July, MASS MoCA is hosting the 2025 edition of the multi-day music festival, LOUD Weekend, which invites artists and performers from multiple genres to its campus, while the FreshGrass Festival taking place September 19-21 will fill the galleries—as well as the fields and courtyards around North Adams—with local art, music, and food.

Speaking of food, the museum campus has a cafe, a Mexican restaurant, an ice cream shop, and a brewery all on-site, catering to any appetite during opening hours. Another potential stop for lunch is boutique hotel Tourists, which serves sandwiches, salads, and snacks at its restaurant—conveniently located on the route from North Adams to Williamstown, which is a perfect next destination.

A small town that revolves around its liberal arts college, Williamstown’s most popular attraction is the Clark Art Institute. This center combines a public art museum with research and academic programs, including a major art history library, and comprises a neoclassical white-marble building Museum Building that contrasts the contemporary concrete Clark Center building by Tadao Ando amongst beautifully landscaped grounds.

This summer, The Clark is presenting “Ground/work 2025,” the second edition of its outdoor sculpture exhibition, featuring newly commissioned, site-specific works by six international contemporary artists, curated by Glenn Adamson. Other exhibitions currently running include a solo show by Philadelphia artist Mariel Capanna; an overview of mid-century modern graphic design; and a series of works by Isamu Noguchi that explore his relationship with time. These are on view concurrently with the institute’s permanent collection, which is particularly rich in French Impressionist and Academic paintings; British oil sketches, drawings, and silver; and works by American artists Winslow Homer, George Inness, and John Singer Sargent.

The Williams College Museum of Art also runs an exhibition program, titled “Object Lab,” which visualizes the institution’s liberal arts curriculum through its museum collection. Faculty work with WCMA staff to select art that connects with course concepts, which this year include Color Theory, and the works are then installed in the galleries, grouped by course. Visitors are encouraged to discover the variety of public art around the college campus, such as Louise Bourgeois’s “Eyes” and Jenny Holzer’s “715 molecules,” at their leisure too.

Smaller regional art hubs include the towns of Great Barrington and Lenox, both home to several independent galleries. The latter also offers a plentiful supply of music and theater over the summer, via packed event programs at multi-venue center Tanglewood, a series of women-focused productions at the WAM Theatre, and daily evening performances of Romeo & Juliet organized by Shakespeare & Company under the Berkshire skies.