A CREATIVE ESCAPE WORTH PLANNING: THE WILLIAMSTOWN THEATRE FEATIVAL

Contributor - Jack Bartholet | Lifestyle Consultant • 7/17/25

In a season where much of the focus is on where to unwind—be it the Hamptons, the South of France, or your favorite stretch of Mediterranean coast—there’s something uniquely refreshing about seeking out culture over coastline. This year, I’d like to suggest a compelling alternative: a weekend escape to the Williamstown Theatre Festival, tucked into the rolling greens of the Berkshires, running now through August 3.

Yes, the scenery is postcard-worthy. But what makes this annual gathering truly exceptional is the energy behind it—blending bold artistic risks with the intimacy of this special town. This year’s festival, under the creative direction of Jeremy O. Harris (the cooler-than-cool playwright of Slave Play, the most Tony-nominated non-musical in history), leans into that spirit in all the right ways.

Whether you’re a longtime theatergoer or someone who simply appreciates a well-constructed weekend away, this festival hits the sweet spot between cultural depth and aesthetic pleasure.

PAMELA ANDERSON IN A TENNESSEE WILLIAMS CLASSIC:

Let’s start with what everyone’s talking about: Camino Real by Tennessee Williams, staged with both bravado and clarity by director Dustin Wills. At the heart of it is actress Pamela Anderson, who is sure to bring a raw, thoughtful, and layered performance—proving once again her capacity to surprise audiences with emotional resonance and intelligence. Anderson made her Broadway debut as Roxie Hart in Chicago, and her recent buzzy film, The Last Showgirl, has us eager to see her in the world of Tennessee Williams. The set design is immersive, the pacing kinetic, and the overall effect is one of true theatrical beauty—the sort of experience only a festival can usher in.

MORE THAN A HEADLINER:

The festival’s true magic lies in its range. Every show this season adds texture and dimension to the whole.

Not About Nightingales, another rarely staged Tennessee Williams piece, brings urgent themes of confinement, survival, and dignity to the fore. Meanwhile, Spirit of the People offers a meditative, movement-driven experience where sound, nature, and storytelling fuse in a way that feels more ritual than performance.

New works like Many Happy Returns and Vanessa offer a contemporary lens on connection, power dynamics, and identity—often set in intimate spaces where you feel close enough to see every emotional flicker. The Things Around Us, an abstract installation-performance hybrid, invites reflection through movement and sound, while the festival’s late-night programming—Late at The Annex (featuring founding member of Vampire Weekend, Rostam) and The Gig: After Moisés and the World of Reason—lets the boundaries between stage and salon melt away. Think of it as a Greenwich Village speakeasy for the creatively inclined.

WHERE TO STAY:

Convenience and charm meet at The Williams Inn, located right in the heart of Williamstown. It’s recently been redesigned with a modern, rustic aesthetic that fits the Berkshires perfectly. You’ll enjoy soft linens, spacious suites, and windows that frame the treetops.

If you’re looking for a touch of nostalgia and a slower pace, The Red Lion Inn in nearby Stockbridge offers old-world hospitality and wide porches perfect for coffee or a nightcap. It’s about a 30-minute drive from the festival, but it makes the whole trip feel like a retreat from time. Enjoy their pool and hot tub, as well as their seasonal live music and magic shows.

WHERE TO EAT:

Dining in the Berkshires can be just as satisfying as the performances. Mezze Bistro + Bar is a local gem and our top recommendation for a pre-theater dinner. Their rotating seasonal menu features ingredients sourced from nearby farms—expect elegant but approachable dishes and an excellent wine list. Be sure to request a seat on the terrace.

For lunch or a more casual option, consider Pera Bistro, known for its modern Mediterranean plates, or The Break Room at MASS MoCA for simple but delicious meals in a stylish setting. If you’re in the mood for a picnic or want to stock your hotel minibar with thoughtful snacks, The Store at Five Corners offers upscale provisions perfect for an impromptu alfresco moment.

MAKE IT A WEEKEND

If you’re already making the drive (approximately 3.5 hours from New York City or 2.5 from Boston), you might as well lean into the escape. The Berkshires are rich in cultural institutions:

The Clark Institute houses one of the country’s finest collections of European and American art. Take time for the grounds as well—the outdoor paths and wooded trails are reason enough to visit.

MASS MoCA delivers bold, contemporary exhibitions in a cavernous industrial space that somehow feels both raw and curated.

Naumkeag is another favorite for a relaxed afternoon—its landscaped gardens and Gilded Age mansion overlook some of the region’s most scenic hillsides.

Each of these pairs beautifully with a performance-packed itinerary. Consider a trip that builds in leisure, exploration, and curated dining.

Williamstown Theatre Festival describes itself as a “temporary society”—a place where actors, artists, and audience members come together each summer to create and witness something ephemeral but profound. That phrasing feels especially apt this season. This isn’t theater for the sake of tradition; it’s theater in dialogue with the world around us. That it happens in such a beautiful, art-rich pocket of the Northeast only enhances its appeal. If you’re looking for a summer weekend that feels both grounded and elevated, Williamstown might be your perfect next chapter.

Contributor — Jack Bartholet | Lifestyle Consultant

Jack effortlessly transitions from the entertainment industry to the world of luxury hospitality and travel, bringing a rich background of collaboration with celebrated artists and extensive personal travel experiences. When not consulting, he can be seen onstage with cabaret and theatre performances. Jack's enduring passion centers on fostering a sense of belonging for LGBTQ travelers wherever their journey takes them.