Just as famous for its landscape as it is for its culture, the Berkshires — a region in Western Massachusetts defined by its rolling mountains — is filled with art, history and a few unexpected adventures.
From world-class performances and festivals to museums celebrating beloved American icons like Norman Rockwell, this scenic New England spot proves to be anything but ordinary.
For some of the best views around, head to Mount Greylock, the highest point in Massachusetts at 3,491 feet. On a clear day, you can see up to 90 miles away across five states, perfect for an enviable selfie.
Nature lovers will want to explore the area’s more than 45 miles of scenic hiking, including a section of the Appalachian Trail.
Always cutting-edge and exciting, the Massachusetts Museum of Contemporary Arts is home to one of the largest collections of modern and mixed-media displays in the country. The sheer amount of artistic talent on offer — with mediums ranging from music, sculpture, dance, film, painting, photography, theater, installations and more — is staggering.
Long-term exhibits, like “Sol DeWitt: A Wall Drawing Retrospective” (on display until 2033) are excellent, but what makes this gallery worth visiting again and again is the variety of temporary shows and events, not to mention an onsite microbrewery that spotlights locally malted grains and hops grown in the Berkshire valley.
To say that Tanglewood is simply the summer home of the Boston Symphony Orchestra doesn’t do it justice. This massive melodic campus is more than a performance venue; it’s an annual ritual for hundreds of thousands of music and dance lovers who come for everything from classical performances by Yo-Yo Ma to a night under the stars with rock legends like John Mellencamp.
Jacob’s Pillow Dance Festival
Another summertime staple in the Berkshires is the Jacob’s Pillow Dance Festival, the country’s longest-running international celebration of all things movement. With more than 50 dance companies and 200 free performances, talks and showcases, the event draws thousands of culture enthusiasts from around the globe each year.
The Mount, Edith Wharton’s Home
Step back in time at The Mount, home of Pulitzer Prize-winning author Edith Wharton, writer of such classics as The Age of Innocence, Ethan Frome and The House of Mirth.
Wharton designed and built The Mount in 1902, based on the principles outlined in her book The Decoration of Houses, which she coauthored with architect Ogden Codman Jr.
Tours of the classical revival house are available, but no visit would be complete without enjoying the three acres of gorgeous formal gardens, also designed by Wharton.
Norman Rockwell Museum
It’s easy to lose yourself in the world of Norman Rockwell at this excellent museum dedicated to the prolific artist. It owns the world’s largest and most significant collection of his work, with nearly 1,000 original paintings and drawings.
Exhibits in the museum include Rockwell’s studio, with his original art materials, library, furnishings and personal items. The gallery also boasts an archive of more than 100,000 pieces documenting the artist’s life.
But perhaps the most interesting display features the illustrator’s 323 Saturday Evening Post covers spanning from 1916 to 1963.
This stunning property is the former Gilded Age home of Joseph Choate, a leading 19th-century attorney. The 44-room mansion and National Historic Landmark was deeded to the nonprofit Trustees of Reservations fully intact, so everything from tools in the barn to clothes in the closets remained as they were in the late 1800s.
While the house is fascinating, the grounds are jaw dropping. The Blue Steps, a series of art-deco-style deep-blue fountain pools flanked by four flights of stairs and a grove of white birches, is easily the most-visited spot on the property.
Be sure to grab your camera before exploring it and the other gorgeous greenery on the grounds, including the Afternoon Garden, Tree Peony Terrace, Rose Garden, Evergreen Garden and the Chinese Garden.
The Clark Art Institute
What was once a private collection in the home of Singer sewing machine heir Sterling Clark and his wife, Francine, during the 1940s is now a unique and incredibly popular Berkshires museum.
Situated within walking distance of Williams College, the gallery features a variety of European and American pieces that spans from the Renaissance to the early 20th century. Works by Winslow Homer, George Inness and John Singer Sargent are among its many highlights.
Hancock Shaker Village
Founded in 1960, the Hancock Shaker Village honors the history of the religious group who thrived here in the 1840s. Step back in time and visit the 20 historic Shaker buildings set among acres of farm, woodland and pasture.
The onsite museum houses hundreds of examples of Shaker furniture, crafts and household items and provides tours of the 750-acre town. Explore the grounds to speak with artisans working in authentic shops with traditional methods.
You also can check out the heritage breed animals roaming the pastures and the heirloom crops planted in the gardens.
This exciting and adventurous aerial park, offering eight different treetop courses, is a blast. Each layout features multiple elements, including high wires, zip lines, balancing logs, rope ladders, cargo nets and suspended bridges that take you through a beautiful hemlock forest.
If heights aren’t your thing, the action-packed playground also has more grounded activities, such as hiking and snowshoeing.