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!

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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.

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Event Highlights for the Week Ahead in & Around #StockbridgeMA

June 26 – July 2, 2026

As America commemorates its 250th anniversary, The Red Lion Inn presents two special programs. On June 28 at 2 p.m., historian Richard Skolnik, Ph.D., offers Against All Odds: Victory in the War for Independence, examining how the colonies prevailed against the world’s most powerful military force. Then on July 1, Voices of Democracy: 250 Years Creating America brings actors and musicians together for an inspiring evening of storytelling and song. Festive dinner and cocktails begin at 4 p.m., followed by the performance from 5:30 to 7:30 p.m.

Music lovers will be drawn to Tanglewood Music Festival, where the summer season continues with the return of the Jazz at Lincoln Center Orchestra and Wynton Marsalis on June 26 at 7 p,m,. The weekend brings two evenings with legendary singer-songwriter Paul Simon on June 27 and 28 at 7:30 p.m., and Jerry Garcia Celebration with the Boston Pops on June 30 at 7 p.m.

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SUMMER BEGINS IN THE BERKSHIRES

June 19–25 Event Highlights in and around Stockbridge, MA

Summer officially arrives on June 21, and Stockbridge is ready. From opening nights on legendary stages and Pride celebrations in historic gardens to new exhibitions, author talks, family activities, and live music throughout the county, the week ahead offers countless ways to experience the arts, culture, and beauty of the region.

Tanglewood Kicks Off Summer

The summer season begins in grand style at Tanglewood Music Festival with the Popluar Artist Series. On June 20 at 7 p.m., Jon Stewart takes the stage with special guest Church and State in a phone-free evening of comedy and commentary. The celebration continues on June 21 at 2:30 p.m. when Yacht Rock Revue brings its acclaimed PRIMETIME presented by CANN tour and a nostalgic soundtrack of ’70s and ’80s favorites.

Powerful Stories Take Center Stage

At Berkshire Theatre Group’s Unicorn Theatre, The American Five opens June 18 and runs through July 11, exploring the lives of Dr. Martin Luther King Jr., Coretta Scott King, Bayard Rustin, Stanley Levison, and Clarence B. Jones in the days leading to the March on Washington. In Lenox, MA, Shakespeare & Company opens its 49th season with Fireflies, running June 19–July 19, a touching story of unexpected romance and second chances.

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BOSTON SYMPHONY ORCHESTRA ANNOUNCES 

2026 TANGLEWOOD SEASON (June 21 to Sept. 2)