Dance Your Way Into Summer’s Final Moments in #StockbridgeMA

There’s still plenty of time to enjoy a Stockbridge getaway! As summer eases into fall, the Berkshires offer beautiful scenery, inspiring arts and culture, historic places, locally owned shops, and delicious dining.

The coming weeks bring a wonderful calendar of events, performances, exhibitions, and seasonal activities throughout Stockbridge and the surrounding Berkshires. Explore the gardens at Naumkeag and Chesterwood, enjoy concerts at Tanglewood, take in a theater performance, or simply slow down and enjoy the charm of a quintessential New England village.

And then comes fall, when the landscape takes center stage. Experience brilliant foliage, scenic roads and trails, farm-to-table dining, and the many special events that make autumn in the Berkshires so memorable.

Whether you’re planning a weekend escape or a longer stay, Stockbridge is ready to welcome you. Come discover what’s happening and make the most of the season!  See What’s Happening Here

Event Highlights for the Week Ahead in & Around #StockbridgeMA

August 21-27, 2026

Missed last week’s highlights (August 14 – 20)? click here.

This week’s highlights include Cynthia Erivo with the Boston Pops at Tanglewood, Prima Music Foundation: Opera Night at Ventfort Hall, Berkshire Opera Festival’s Lucia di Lammermoor at the Mahaiwe, Free Community Day at Berkshire Botanical Garden, GATO6 featuring Suzi Stern at The Mount, Summer Saturdays at the Norman Rockwell Museum, and Ballet Hispánico at Jacob’s Pillow.

Add performances at ArtsAlive/Chesterwood, Berkshire Theatre Group, and Shakespeare & Company; tours of our historic sites; enjoy family activities; and more, and you’ll find countless ways to experience the arts, history, music, and natural beauty of Stockbridge and the Berkshires this week. Read More

Event Highlights for the Week Ahead in & Around #StockbridgeMA

August 14 – 20, 2026

Missed last week’s highlights (August 7 – 13)? click here.

This week’s highlights include the Kids Summer Sculpture Studio at Chesterwood, 8th Annual Art of Brewing Festival at the Norman Rockwell Museum, Summer Author Series at the Mount Nicholas Boggs, Baldwin: A Love Story, The Martha Graham Dance Company at Jacob’s Pillow, Maestro of the Movies: A Tribute to John Williams and Brandi Carlile at Tanglewood and Indigo Comedy Night with Mike Lebovitz at Mahaiwe Performing Arts Center. Add performances at Berkshire Theatre Group or Shakespeare and Company, readings at Ventfort Hall, tours of our historic sites, enjoy family activities, and more, and you’ll find countless ways to experience the arts, history, music, and natural beauty of Stockbridge and the Berkshires this week. Read More

Event Highlights for the Week Ahead in & Around #StockbridgeMA

August 7 – 13, 2026

Missed last week’s highlights (July 31 – August 6)? click here.

This week’s highlights include the 56th Annual Grow Show at Berkshire Botanical Garden, the opening of Hamlet at Shakespeare & Company, An American Journey with Yo-Yo Ma and Friends and Hugh Jackman with the Boston Pops at Tanglewood, Opera Night! – American Music from the Operatic Stage at Chesterwood, Free Community Day at The Mount, and the Curator Tour: American Stories – Revolution to Rockwell at the Norman Rockwell Museum. There’s something for everyone to enjoy throughout the Berkshires this week!

Learn More!

Event Highlights for the Week Ahead in & Around #StockbridgeMA

July 31 – August 6, 2026

Missed last week’s highlights (July 24 – 30)? click here.

This week’s highlights include Tanglewood on Parade, the Life-Sized Candy Land Board Game at the Stockbridge Library, and the opening of The Legend of Georgia McBride at Berkshire Theatre Group’s Colonial Theatre.

Enjoy world-class dance as Germany’s Gauthier Dance presents The FireWorks Project at Jacob’s Pillow and experience the 2026 Gala: Anthony Roth Costanzo at the Mahaiwe Performing Arts Center. Additional highlights this season include Shake It Up: The Remix at Shakespeare & Company, Music Mondays featuring Misty Blues at the Berkshire Botanical Garden, and Chesterwood’s ArtsAlive! series with five engaging programs celebrating the arts. The Norman Rockwell Museum offers its popular guided Walking Tour of Historic Stockbridge, while The Mount’s Summer Author Series welcomes acclaimed author Jeff Chang for a special presentation.  READ ABOUT ALL EVENTS

Event Highlights for the Week Ahead in & Around #StockbridgeMA

July 24 – 30, 2026

Missed last week’s highlights (July 17 – 23)? click

This week’s highlights include the 6th Annual Community Dog Show at the Stockbridge Library, Music Mondays featuring the Lucky 5 at the Berkshire Botanical Garden, Moth Night at Chesterwood, and Voices of Democracy: Imagining America: The Next 250 at The Red Lion Inn. Enjoy jazz with the Branford Marsalis Quartet at the Mahaiwe Performing Arts Center, the opening of Frankie and Johnny in the Clair de Lune at Shakespeare & Company, and the return of Australia’s Circa Contemporary Circus with Wolf at Jacob’s Pillow. Add performances at Berkshire Theatre Group, concerts, museum exhibitions, garden tours, family activities, and more, and you’ll find countless ways to experience the arts, history, music, and natural beauty of Stockbridge and the Berkshires this week. READ MORE

Event Highlights for the Week Ahead in & Around #StockbridgeMA

July 17 – 23, 2026

Missed last week’s highlights (July 10 – 16)? click here.

This week features the opening of Lovesong at the Unicorn Theatre, A.I.M. by Kyle Abraham presents U.S. premier of White Space at Jacob’s Pillow, Tom Papa: Grateful Bread Tour at Mahaiwe, Garden Tea Party at Chesterwood, Keep MOO’ving 5k at Highlawn Farm, “Weird Al” Yankovic: Bigger & Weirder 2026 Tour at Tanglewood and so much more..  READ MORE

Event Highlights for the Week Ahead in & Around #StockbridgeMA

July 10 – 16, 2026

Missed last week’s highlights (July 3 – 9)? click here.

Summer is in full swing, bringing an exceptional lineup of music, theater, art, gardens, history, and family fun throughout Stockbridge and the Berkshires. This week features the annual book sale at the Stockbridge Library, the opening of Rebel Town the Musical, Popular Artist Series Ziggy Marley and Trombone, Pillow Pride Weekend, Free Community Day and more.  READ MORE

Long summer days bring a full week of music, theater, art, gardens, and history across Stockbridge and the Berkshires. Independence Day programming, America250 reflections, world-class performances, and lively community events fill the holiday week with ways to explore and connect across the region.

INDEPENDENCE DAY

Norman Rockwell Museum — We Hold These Truths

July 4 | 10 a.m.– 4 p.m.

Celebrate Independence Day with one of the week’s most meaningful gatherings, presented in partnership with the W.E.B. Du Bois Freedom Center. We Hold These Truths features a community reading of the Declaration of Independence led by Berkshire residents and civic voices, accompanied by live music from Wanda Houston, Rob Putnam, and Doug Mishkin. Families can take part in hands-on art activities, and visitors are invited to experience the museum’s powerful exhibition American Stories: Revolution to Rockwell, offering a reflection on the nation’s past through illustration and storytelling.

READ MORE ABOUT UPCOMING EVENTS