New England’s Cultural Mecca: A Guide to The Berkshires

You probably know about Upstate New York’s creative mecca, Hudson Valley, but have you heard of the nearby Massachusetts Berkshires?

A rural region in the mountains of western Massachusetts dotted with villages and towns, the Northern Berkshires is known for its rich cultural and artistic scene, as well as its fall foliage and overall rustic idyll. 

We spoke with Nina Keneally, a former theater producer and gallerist and friend of All Roads North, to get the intel on this flourishing artistic oasis.

“You could probably find a new trail to hike every day of the year for at least three or four years because there is so much nature, but especially in the summer season, you also couldn’t begin to do everything that’s offered here artistically,” Keneally said. 

History of the Arts in the Berkshires

Jacob's Pillow

Jacob’s Pillow

The Berkshires’ convenient location just a few hours away from Boston and New York City has long provided the perfect country escape for wealthy city folk. Where the money went, the arts soon followed. 

“Especially in the Southern Berkshires, a lot of arts developed here because people had summer homes here. It’s always been a summer escape for those artists– classical artists, musicians and dancers,” Keneally said.

Centers of education like Williams College also contributed to the cultural scene by supplying strong arts programs and attracting young creatives. Thomas Krens was director of the Williams College Museum of Art and an integral figure in the Berkshires’ artistic renaissance. During his time at Williams, inspiration struck him for an unlikely contemporary art museum in the Berkshires.  

“Thomas Krens knew about this building in North Adams, which had once been an electric plant but had been vacant since the 70’s,” Keneally said. “He had the idea to put this contemporary art museum there that could handle very large works of art that really didn’t have anywhere else to go. That was the genesis of MASS MoCA.”

Krens’ latest vision is for a new museum focused on model railroads and architecture in the Northern Berkshires, which is currently under construction. The project, called the Extreme Model Railroad and Contemporary Architecture Museum, promises to deliver a “museum-theme park” experience, completed as early as 2025.

Our Favorite Art and Music in The Berkshires

The Clark Institute

The Clark Institute

As for now, the galleries, museums, festivals and showings in the Berkshires are endless across seemingly every artistic category– from visual arts to dance to music. From monumental museums to trendy galleries, here are a few of the top attractions: 

  • Massachusetts Museum of Modern Art (aka MASS MoCA): A modern art museum in North Adams housed in a former electric plant with an emphasis on large-scale, immersive works
  • Tanglewood: The famed summer home of the Boston Symphony Orchestra and one of the world’s most beloved music festivals.
  • Ferrin Contemporary: A 40-year old modern ceramic art gallery, located on MASS MoCA’s 16-acre campus.
  • Jacob’s Pillow: The 220-acre home to America’s longest-running international dance festival which hosts performances, talks, and events, as well as dance training.
  • The Clark Art Institute: Both an art museum and a distinguished center for research and higher education. Keneally said The Clark is the best in the area in regards to the landscape and architecture.
  • MCLA Gallery 51: Run by the Massachusetts College of Liberal Arts, Gallery 51 exhibits art from an international mix of both emerging and mid-career artists.
  • Bang on a Can: The Bang on a Can Summer Music Festival at MASS MoCA is a 3-week musical fest dedicated to adventurous, contemporary music.


Suggested Itineraries in The Berkshires:

Mass Moca exhibit


Explore the captivating artistic scene in the Massachusetts Berkshires yourself. All Roads North will pair you with artists and expert guides to introduce you to the heart of the region. 

Start with some inspiration from these itineraries: 

Luxury New England Road Trip Meet Boston academics, Maine lobstermen, and brewers from Vermont, while staying in style at some of the region’s top hotels.

New York to Montreal Road Trip: Where Past Meets Present – Whether exploring the Great Camps of the Adirondacks, cheering on your horse at Saratoga Springs or biking amongst the outdoor exhibits of a forward-thinking art center in Hudson Valley, this New York to Montreal road trip balances the glamor of an era gone by with the area’s forward-thinking, contemporary heart.


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