Art and Performance in the Berkshires: A Look Behind the Scenes - July 14, 2019 - Atlas Obscura Trips


Art and Performance in the Berkshires: A Look Behind the Scenes

In the rolling green hills of the Berkshires, art and history are everywhere: Norman Rockwell’s former studio; a stop on the Underground Railroad that's now a renowned contemporary dance venue; a world-class art collection relocated by its New York City owners safely out of range of Cold War nuclear disaster; and a mountain that provided inspiration to writers like Melville and Thoreau, to name just a few of the highlights. 

In summertime, the region comes alive with festivals celebrating some of the best and most groundbreaking art, music, and theater from around the world. During our time here, we’ll go behind the scenes, meet performers and directors, and have opportunities to engage with insiders and experts in the arts.

This trip is best for people who are...

  • Excited to experience world-class dance, visual art, theater, and music.
  • Ready to explore the beautiful landscape of the Berkshires, whether strolling through town or climbing a grassy hill to take in views of the surrounding mountains. Travelers should be prepared to walk 2 to 3 miles a day, often on grass or dirt paths. 
  • Curious to discover the overlooked corners of local galleries and go behind the scenes at world-class performances.

On our four-day excursion, we’ll indulge our creative sides in these picturesque woodlands that have inspired thinkers and artists for centuries. We’ll dine with a dancer from Jacob’s Pillow, the oldest summer dance festival in the U.S., and discover under-the-radar Picasso works amid wonderful abstract art at the Frelinghuysen Morris Home & Studio. We’ll head to the orchestra and to the theater, each followed by private Q&As with the performers. In between events, we’ll enjoy delicious meals at local landmarks, and explore the bucolic grounds of famed institutions like The Clark, Mass MoCA, and the Norman Rockwell Museum. We’ll also leave plenty of time to relax, soak in the sun, and relish the beautiful mountain views.


  • Dance and dine: Enjoy a performance at Jacob’s Pillow, followed by an exclusive tour of the grounds and dinner with one of the dancers.
  • Exquisite art collections: Discover 19th-century French art, cubist frescos, and lesser-known works by Picasso, with expert-led tours.
  • Norman Rockwell country: Admire the paintings and illustrations of Norman Rockwell while exploring the very same rural American towns he immortalized in his work.

Note: This itinerary will be updated once performance details are announced for the 2019 season. Changes to the schedule may be made as a result.

Day 1
Movement in the Mountains
  • Arrive in Stockbridge at the Red Lion Inn, a Berkshires landmark, where we’ll get to know each other over lunch. Enjoy the fresh fare while learning about the fascinating history of this colonial inn, with some time afterwards to explore its hidden corners.
  • After lunch, we’ll kick off the trip with a matinee performance at the famed Jacob’s Pillow, a world-renowned dance venue with outdoor stages backdropped by wooded hills. Originally a mountaintop farm, the site was a stop on the Underground Railroad before becoming a dance retreat in 1931. Today it is the longest-running dance festival in the U.S. and a National Historic Landmark.
  • Following the performance, we’ll be treated to a private tour of the grounds by Jacob’s Pillow’s director of preservation.
  • To cap off our first day, we’ll enjoy a delicious dinner on-site in the company of one of the dancers, then head back to our rooms at Tourists, a mountain oasis overlooking the Hoosic River.
Day 2
Hidden Art & Otherworldly Acoustics
  • After a leisurely alfresco breakfast on the deck, we’ll head out to Mass MoCA, the largest contemporary art museum in the U.S. We’ll get a private guided tour of the museum’s gigantic gallery spaces, and then you’re free to continue to explore on your own. (Don’t miss James Turrell’s Into the Light exhibit!)
  • Enjoy lunch at your leisure and take a couple of hours to wander the museum’s lovely grounds. You can even take a hike on one of the many nearby trails.
  • Later this afternoon, we’re off to the Frelinghuysen Morris House & Studio for a private guided tour of the abstract artists’ former home and studio. This unique space includes obscure works by Pablo Picasso, as well as one very cool bar tucked under their staircase.
  • After a delectable French dinner, we’ll take in a symphony at the famed Ozawa Concert Hall. The building itself is a thing of beauty, and the wooden interior’s acoustics are otherworldly. Stay in your seats and relax while the rest of the crowd shuffles out. Performers from tonight’s show will spend some time chatting with us and answering questions after the show.
Day 3
Intimate Galleries & Experimental Drama
  • After a leisurely morning, we’re off to see the wonderful collection at the Clark Art Institute, known for its intimate galleries and stunning natural environment. We’ll take a private guided tour, followed by time to roam and explore. Make sure you save some time to climb the hill behind the museum and experience Thomas Schütte’s Crystal. There, you’ll want to wait a bit to not only catch your breath but to take in one of the best views in the Berkshires.
  • After lunch at the museum cafe, we’ll take the afternoon to explore the quaint towns and nature trails of the Berkshires. Our guides will have a bevy of insider recommendations, from art galleries to hiking and everything in between.
  • After dinner at a local bistro, we’ll make our way to the Williamstown Theatre Festival for a brand-new play at the experimental Nikos Stage.
  • Stay in your seats post-performance for an opportunity to speak with the show’s actors and directors.  
Day 4
Norman Rockwell Send-Off
  • After breakfast, we’ll visit the Norman Rockwell Museum. No trip to the Berkshires is complete without a morning at this museum, home to 998 original Rockwell paintings and drawings, including all 323 of his Saturday Evening Post covers. Visit his studio (where it feels like he just stepped out and will return at any moment!), explore the grounds, and take in the scenic sweeping views of the Housatonic Valley.
  • At lunchtime, we’ll reconvene to enjoy our last meal together on the scenic grounds of the museum.
  • After making the trip back to Stockbridge, it’s time to say our farewells.
The Fine Print


  • The services of two expert trip leaders.
  • Accommodations at Tourists.
  • Ground transportation.
  • Private guided tours through museums and other venues.
  • Entry to all performances and activities as mentioned in the itinerary.
  • All dinners and breakfasts at top restaurants, two catered lunches, as well as snacks and beverages between meals.
  • Baggage transfer and porterage.
  • All gratuities at hotels, restaurants, and other group venues.


Travelers should be comfortable standing and walking for several hours each day, often on grassy hills or well-maintained dirt paths. We’ll be outdoors much of the time, so come prepared with sunscreen and a light jacket. 


Our trip begins in Stockbridge, MA, located a three-hour drive north of New York City, or a two-hour drive west of Boston, MA. Travelers should plan to arrive at the Red Lion Inn by 12 p.m. on Sunday, July 14. Our trip will conclude after lunch at the Norman Rockwell Museum on Wednesday, July 17. You're welcome to depart after 1:30 p.m. on the 17th, or stay and explore the Berkshires on your own. 


Itineraries are subject to change. This particular tour has been designed with specific activities and events in mind, whose schedules and availabilities may change in the coming months. If any activity or attraction that is advertised is missed or not available, then we will replace it with another activity or location of significant interest and value.


A deposit of $500 is required to hold your space. The final payment of $1,650 will be due by May 31, 2019. All reservations will be final after this date and subject to our cancellation policy. By submitting your deposit, you agree to the Terms & Conditions. For travelers wishing to have single accommodations during the trip, an additional $450 will be included in the final payment.


  • Airfare, driving and/or other transportation to and from the Berkshires.
  • Two lunches, as well as any additional meals and drinks outside of Atlas Obscura offerings.
  • Travel insurance (recommended).
  • If applicable, applying for a U.S. visa.

Other Trips You Might Like