What to Do in the Berkshires: 9 Fun Things To Do

You’ll find endless adventures in the Berkshires, from hiking Massachusetts’s highest peak at Mount Greylock to catching world-class performances at Tanglewood. Explore MASS MoCA’s contemporary art installations, tour Edith Wharton’s stunning estate, and take an easy walk to spectacular Bash Bish Falls. Don’t miss Stockbridge’s historic Main Street, the Norman Rockwell Museum, and Great Barrington’s incredible farm-to-table dining scene. Each destination offers unique experiences that showcase why this region captivates visitors year-round.

Hike to the Summit of Mount Greylock for Appalachian Trail Views

As Massachusetts’s highest peak at 3,491 feet, Mount Greylock delivers some of the state’s most rewarding hiking experiences, especially where 11.5 miles of the Appalachian Trail cross its ridgeline.

You’ll enjoy panoramic views of the Taconic Range, Green Mountains, and Berkshires from the summit’s 90-foot Veterans War Memorial Tower.

Choose your route based on fitness level and time. The Hopper Trail‘s the quickest at 1.7 miles but steep.

Bellows Pipe offers a moderate 5.9-mile round trip, while Gould Trail’s 5.5 miles suit beginners with gentler grades.

The reservation’s 70 miles of trails let you create loops combining AT sections with lower forest paths. The area was originally home to the Mohican people, an Algonquin-speaking tribe who used the region before European settlement.

Pack layers and sturdy boots – summit weather changes quickly, and trails feature rocky, rooty terrain.

Experience World-Class Art at MASS MoCA in North Adams

After soaking in mountain vistas, shift your cultural focus to North Adams, where MASS MoCA transforms a massive 19th-century factory complex into one of America’s most ambitious contemporary art destinations.

You’ll explore 250,000 square feet of exhibition space – the largest contemporary art museum in North America by gallery footage – welcoming 220,000 visitors annually.

Don’t miss Sol LeWitt’s stunning wall drawing retrospective featuring 105 large-scale works across three floors. Reserve timed slots for James Turrell’s immersive light installations like C.A.V.U., which manipulate your perception through carefully controlled environments.

Interactive experiences include Gunnar Schonbeck’s participatory sound installation where you’ll play unconventional handmade instruments. Beyond visual art, MASS MoCA presents live performances throughout the year, adding dynamic theatrical and musical elements to your cultural experience.

The museum’s rotating exhibitions ensure fresh experiences with each visit, while the adaptive reuse of historic industrial buildings creates dramatic backdrops for monumental contemporary works.

Catch a Boston Symphony Orchestra Performance at Tanglewood

While MASS MoCA showcases cutting-edge contemporary art, Tanglewood offers a completely different cultural experience where you’ll hear world-class classical music under the stars.

Since 1937, this sprawling campus in Lenox has been the Boston Symphony Orchestra’s summer home, featuring lush lawns and scenic mountain views.

You’ve got two seating options: covered seats inside the Koussevitzky Music Shed or lawn tickets where you can picnic during performances.

Bring blankets, low chairs, and food for a relaxed evening under the open sky.

The season runs late June through August, with afternoon matinees and evening concerts featuring renowned soloists like Yo-Yo Ma and Lang Lang. This cultural destination contributes over $100 million annually to the local Berkshire economy.

Book early for popular events like Star Wars screenings and holiday performances, as thousands attend these high-demand shows.

Explore Edith Wharton’s Estate and Gardens at The Mount

Step into the world of America’s first female Pulitzer Prize winner at The Mount, where Edith Wharton designed and built her dream estate in 1901. You’ll tour the Georgian Revival mansion where she wrote classics like “The House of Mirth” and “Ethan Frome” during her most productive decade.

The self-guided tours let you explore at your own pace through rooms that hosted literary giants like Henry James.

Don’t miss the stunning 49-acre grounds featuring Italian walled gardens, terraced lawns, and scenic views of Laurel Lake. The estate offers over 100 annual programs including readings and workshops. Browse through The Mount’s Library housing approximately 2,700 volumes from Wharton’s personal collection.

Visit during summer for extended hours, or check their seasonal schedule for special events that won’t break your budget.

Take the Short Walk to Bash Bish Falls

Just a short drive from Lenox’s literary landmarks, you’ll discover Massachusetts’ most spectacular waterfall tucked away in the Berkshire Mountains. Bash Bish Falls drops over 60 feet into a dramatic plunge pool, making it the state’s highest single-drop waterfall.

You’ve got two parking options. The Massachusetts side offers the shortest route at 0.6 miles round trip, but expect steep, rocky terrain with grades up to 25%.

If you prefer easier walking, head to the New York side via Taconic State Park for a gentler 1.5-mile round trip on crushed stone paths. Follow the white blazes that mark this well-maintained trail with its steady but manageable incline.

Both parking lots are free, and you’ll walk through beautiful hemlock forests. The NY trail even crosses the state border, adding a fun geographic element to your waterfall adventure.

Tour the Living History of Hancock Shaker Village

Watch costumed interpreters demonstrate traditional crafts like broom-making and chair construction while learning about Shaker innovations that shaped American design.

The working farm continues historic agricultural practices, and miles of trails let you experience the broader landscape that once supported this self-sufficient community through farming and seed production. The village showcases remarkable architecture including the 1826 Round Stone Barn, one of the few surviving examples in Massachusetts, designed with a circular layout for maximum farming efficiency.

Discover French Impressionist Masterpieces at the Clark Art Institute

After experiencing the simple, functional beauty of Shaker design, you’ll find a striking contrast at the Clark Art Institute in Williamstown, where ornate French Impressionist masterpieces fill elegant galleries.

You’ll discover an exceptional collection featuring over seventy major 19th-century European paintings, including works by Monet, Renoir, Degas, Manet, and Pissarro.

The Clark’s crown jewel is its outstanding Renoir collection—31 major works showcasing the artist’s figure paintings, portraits, and luminous outdoor scenes.

You’ll also see pieces by Bonnard, Toulouse-Lautrec, and Gauguin that extend into Post-Impressionism.

The museum thoughtfully displays academic painters like Bouguereau alongside Impressionist works, letting you compare traditional Salon style with the avant-garde movement that challenged it. The collection reflects the vision of Sterling Clark, a self-trained connoisseur who assembled these masterpieces in the early 20th century.

It’s an affordable way to see world-class art.

Stroll Through Historic Stockbridge and Visit Norman Rockwell Museum

While the Clark Art Institute showcases European masterpieces, you’ll find quintessentially American art just a short drive south in Stockbridge, where Norman Rockwell spent his final 25 years capturing small-town life on canvas.

Start by walking Historic Main Street, which looks remarkably like Rockwell’s 1967 painting “Stockbridge Main Street at Christmas.” You’ll see the same 19th-century storefronts and white church steeple that inspired his work.

The Norman Rockwell Museum houses the world’s largest collection of his art—998 original paintings and drawings. Don’t miss his preserved studio, relocated to the museum’s 36-acre campus. The museum also features works from other American illustrators like Scott Baka, Isabel Bishop, and James Montgomery Flagg, providing a broader perspective on the American illustration tradition.

From May through October, you can tour this 1830s carriage barn filled with his easel, props, and materials, offering insights into his creative process.

Enjoy Farm-to-Table Dining in Great Barrington’s Food Scene

Just thirty minutes south of Stockbridge, Great Barrington has emerged as the Berkshires’ premier dining destination, where farm-to-table isn’t just a trend—it’s a way of life. You’ll find exceptional options for every budget and occasion.

For upscale dining, book cafeADAM, which sources pasture-raised meats and sustainable seafood while harvesting herbs on-site. Prairie Whale offers rustic, ingredient-driven dinners that require Resy reservations. No Comply Foods takes a creative “post-farm-to-table” approach with dinner Wednesday through Saturday and weekend brunch.

Budget-friendly Marketplace Café serves locally sourced sandwiches, salads, and flatbreads perfect for casual meals. Fiddleheads Grille provides family-friendly fare with fresh, hearty dishes.

Most restaurants participate in Berkshire Grown networks, ensuring your meal supports local farmers while delivering peak seasonal flavors. The dining scene also features establishments like MoonCloud, which combines expert mixology with carefully crafted small plates.

The Sum Up

You’ve got plenty of options to fill your Berkshires getaway without breaking the bank. Mix free outdoor adventures like hiking Mount Greylock with affordable cultural experiences. Pack lunches for trail days, visit museums during off-peak hours for better rates, and don’t miss the free outdoor concerts at Tanglewood. Whether you’re drawn to art, nature, or history, the Berkshires deliver unforgettable experiences that’ll keep you coming back for more.