Whether you’re visiting for a weekend or an extended getaway, the Berkshires offer something to discover around every corner. You can spend the morning hiking, the afternoon visiting museums or historic estates, and the evening enjoying a concert at Tanglewood. With our Stockbridge bed and breakfast as your home base, many of the region’s top Berkshire activities are just a short drive away.
Music & Theater
From iconic summer concerts to award-winning theater productions, the Berkshires offer unforgettable performances in every season.
- Tanglewood: The undisputed crown jewel of the region. As the summer home of the Boston Symphony Orchestra (BSO), it offers an essential Berkshires experience: buying lawn tickets, grabbing one of our gourmet picnic packages, and listening to world class classical or contemporary music under a canopy of stars. The season runs from June through September.
- Jacob’s Pillow: Nestled in the woods, this historic site hosts one of the most prestigious dance festivals in the world every summer. You can catch everything from classical ballet to cutting edge hip-hop and international troupes.
- The Theater Scene: For incredible acting, standard setting productions, and thought-provoking storytelling, check out the region’s powerhouse resident theater companies like Barrington Stage Company, Shakespeare & Company, and WAM Theatre
- Mahaiwe Performing Arts Center: A beautifully restored historic theater offering year-round music, dance, comedy, and classic movies.
Museums & Historical Landmarks
History and creativity run deep in these hills. You can spend days hopping between Gilded Age mansions and massive, world-renowned art spaces.
- MASS MoCA: One of the largest contemporary art museums in the country. Housed in a sprawling, converted 19th-century factory complex, the scale of the installations here is breathtaking. A full day can easily disappear as you explore the massive, multi-story galleries.
- The Clark Art Institute: Renowned for its exceptional Impressionist paintings, stunning architecture, and peaceful walking trails that integrate the museum right into the landscape.
- Norman Rockwell Museum: Houses the world’s largest collection of original artwork by Rockwell, offering a nostalgic and insightful look at American culture.
- The Mount: The gorgeous estate designed and lived in by author Edith Wharton. The gardens alone are worth the visit.
- Naumkeag & Chesterwood: Naumkeag is famous for its stunning, whimsical architectural gardens and seasonal celebrations—including the incredible Naumkeag Pumpkin Show, Winterlights, and the Daffodil & Tulip Festival. Meanwhile, Chesterwood preserves the historic home and studio of Daniel Chester French, the sculptor of the Lincoln Memorial.
- Hancock Shaker Village: A living history museum with 20 historic buildings (including the famous Round Stone Barn) that brings the beautifully simple heritage of the Shakers to life.
Outdoors & Hiking
When you need to unplug, the natural terrain of the Berkshires offers everything from manicured botanical walkways to rugged stretches of the Appalachian Trail.
- Mountain Greylock: The highest peak in Massachusetts. Features panoramic multi-state views, a historic summit lodge, and a crossing point for the famous Appalachian Trail.
- Pleasant Valley Wildlife Sanctuary: Miles of pristine trails, active beaver ponds, and a vibrant educational nature center perfect for families.
- Berkshire Botanical Garden: A gorgeous, peaceful collection of public display gardens, perfect for a slower-paced afternoon.
- Olivia’s Outlook & Gould Meadows: Olivia’s Outlook offers easily accessible, postcard-perfect views over the Stockbridge Bowl, while Gould Meadows features tranquil lakeside trails.
Breweries, Distilleries, & Local Farms
You can’t visit the area without tasting the local flavor. The Berkshires’ agricultural scene seamlessly blends historic, working family farms with modern craft beverage producers.
- Balderdash Cellars: Bring a blanket and find a spot on the grass at this beautiful hillside winery. It’s the perfect place to pair exceptional craft wines with breathtaking, panoramic lake and mountain vistas, often accompanied by the sounds of local live music.
- Bright Ideas Brewing: Located right on the MASS MoCA campus, making it the perfect spot to grab a refreshing craft beer after a long day of looking at art.
- Berkshire Mountain Distillers: Award-winning regional pioneers in craft spirits, producing fantastic artisanal gin, bourbon, and rum.
- Hilltop Orchards: A historic farm where you can hike or cross-country ski the trails, pick your own apples in the fall, and enjoy fresh cider donuts and hard cider.
- High Lawn Farm: A beautiful historic farmstead offering exceptional farm-to-table dairy products, from artisanal cheeses to decadent gourmet ice cream. It is a true working farm experience, complete with high-quality treats and the chance to visit the baby calves in the barn.
FAQ About Berkshire Activities
What are the most popular Berkshire activities?
Some of the most popular Berkshire activities include attending a concert at Tanglewood, visiting the Norman Rockwell Museum or MASS MoCA, hiking Mount Greylock, touring historic estates like The Mount and Naumkeag, and enjoying local wineries, farms, and scenic drives throughout the region.
What attractions are closest to Stockbridge?
Many of the Berkshires’ most popular attractions are just minutes from Stockbridge, including Norman Rockwell Museum, Naumkeag, The Mount, Berkshire Botanical Garden, Tanglewood, and Chesterwood.
How many days should I spend in the Berkshires?
A three- to four-day getaway gives you enough time to experience the area’s museums, outdoor recreation, restaurants, and performing arts while still enjoying a relaxing pace.
Are the Berkshires good for couples?
Absolutely. The Berkshires are a favorite destination for romantic getaways thanks to scenic mountain views, charming small towns, wineries, fine dining, luxury inns, live performances, and peaceful hiking trails.
What is there to do in the Berkshires year-round?
Every season offers something unique. Spring brings gardens into bloom, summer features concerts and festivals, fall showcases spectacular foliage and apple orchards, and winter offers snowshoeing, cross-country skiing, holiday events, and cozy fireplaces.
Stay Near the Berkshires’ Top Attractions
After a day filled with unforgettable Berkshire activities, there’s nothing better than returning to a peaceful place to unwind. Inn at Stockbridge is centrally located near many of the region’s most popular attractions, making it easy to spend less time driving and more time exploring. Whether you’re planning a romantic getaway, an arts-focused vacation, or an outdoor adventure, our welcoming accommodations provide the perfect home base for experiencing the very best things to do in the Berkshires.
