There’s no single way to experience a Berkshire summer—but in Stockbridge, MA and its neighboring towns, the season unfolds as one continuous cultural journey. A morning in the galleries can lead to an afternoon in the gardens, followed by an evening concert beneath the stars or a late-night jazz set in a historic inn.

In summer 2026, that rhythm carries special resonance as many of the Berkshires’ leading institutions reflect on America’s story in honor of the nation’s 250th anniversary. Across the region, museums, theaters, music venues, and historic estates are presenting exhibitions, performances, conversations, and celebrations that connect past and present in fresh and inspiring ways.

Whether you arrive for a weekend or linger for the summer, the Berkshire calendar offers countless ways to move between inspiration, relaxation, and discovery.

The calendar is full! Read the Full schedule here.

Stockbridge, MA blends rich culture, breathtaking outdoor experiences, and historic small-town charm for the ultimate spring escape. Picture yourself wandering through our museums, charming shops, and vibrant galleries. If you’re feeling adventurous, lace up those hiking boots and embark on scenic trails that reveal nature’s splendor. As you meander through our blooming gardens or indulge in delicious local bites and brews, you’ll find that every corner of Stockbridge invites you to engage, explore, and enjoy. Our New England Inns, B&Bs and Hotels offer specials and packages. Stockbridge is easily accessible, making it the ideal destination for a weekend getaway or an extended stay. Read the entire Schedule

Rediscover the joys of the holidays in Stockbridge, MA, where the town transforms into a magical New England village, adorned with twinkling lights and charming holiday wreaths that evoke the spirit of the season. This enchanting destination offers a delightful array of family-friendly activities that promise to create cherished memories for all. From captivating live performances and historic property tours to bustling holiday markets and the mesmerizing Winterlights display, there’s truly something for everyone to enjoy. Don’t miss the Rockwell Holidays at the Museum, where art and tradition come alive, or the unique shops and restaurants that showcase the best of local commerce. And of course, Santa himself will be making appearances, adding an extra sprinkle of joy to this festive season. Join us in celebrating the warmth and community spirit that makes Stockbridge a quintessential holiday experience, where every moment spent here is sure to inspire and delight! LEARN MORE

Looking for a fun fall getaway? When the air turns crisp and the leaves start to change, there’s no better place to be than in Stockbridge, MA. Whether your perfect day involves fall festivals, shopping in one-of-a-kind boutiques, getting outdoors in all that nature has to offer, experiencing history and art, Stockbridge is guaranteed to please. Come & Stay in our quintessential New England town! Plan a weekend escape or an extended getaway to see the Autumn Leaf Show. Start your visit at StockbridgeChamber.org. READ MORE

Event highlights for the week ahead in and around #StockbridgeMA (August 22-31)

Coming up in the #StockbridgeMA area: Keith Lockhart 30th anniversary concert at Tanglewood, Judy Collins in conversation with Andre Bernard at the Mount, Berkshire Woodworkers Guild at Berkshire Botanical Garden, Shakespeare’s Circus & the Bard, Bidwell’s Private Garden tour, The Knights return to the Clark and more!  Read the entire Schedule

Coming up in the #StockbridgeMA area: Dying is No Excuse opens at the Unicorn Theatre, Emanuel Ax, Leonidas Kavakos, Yo-Yo Ma, and Antoine Tamestit perform at Tanglewood, Touch of RED by Shamel Pitts | TRIBE at Jacob’s Pillow, The BTU’s at Berkshire Botanical Garden Music Mondays, Pulitzer Prize finalist Dava Sobel presents The Elements of Marie Curie at the Mount, 5th Annual Community Dog Show at The Stockbridge Library, Ghost Tours, Tea Talks, Family activities, and so much more. Event Highlights for August 1-7, 2025. Read more

Coming up in #StockbridgeMA area:  A very special evening with Emmylou Harris & Graham Nash, Keep MOOving 5 K Race, Paul Reiser, Gary Gulman, opening of August Wilson’s The Piano Man and Agatha Christie’s The Mousetrap, Afro Latin Dance Company Sekou McMiller & Friends, Author Tess Chakkalakal, Fun Appraisal events of Jewelry and Antiques, Ghost Tours, Tea Talks, Family activities, and so much more. Event highlights for (July 25-31) Read More