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

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

Coming up in the #StockbridgeMA area: Fete des Fleurs: A Midsummer Night’s Dream fundraiser, Local collaborations of Music, Opening of Outdoor Sculpture exhibition, W.E.B Du Bois events, Timeless classics in Theatre and Movies, Fun Appraisal events of Jewelry and Antiques, Dance, Family activities, and more. Event highlights for (July 18-July 24)  Read More

Read what’s happening here this Fall.

Posted September 15, 2017
By Margaret D. Kerswill

Looking for a festive way to celebrate Halloween with your family? Stockbridge offers a few opportunities to scare up some fun and frights for all ages.

About three quarters of a mile from downtown Stockbridge you’ll find Naumkeag, a Trustees of Reservations property and the former country estate of noted New York City lawyer Joseph Hodges Choate, located at 5 Prospect Hill Road. Creep through the woods at night during the annual Pumpkin Trail on October 13 & 14 as 200 carved jack-o-lanterns light your way. Listen for the woodland creatures on the trail who will greet you and regale you with funny and informative stories of their nocturnal activities. Ideal for kids under 12.

Feeling a little more daring? Ready to be frightened in grand Berkshire style? Visit Naumkeag October 20 & 21 and 27 & 28 for their recently resurrected Annual Halloween Haunted House. Be prepared to be scared as you stroll the gardens and tour all three floors of the Gilded Age “cottage” where ghosts and ghoulish creatures await you. Recommended for ages 12+ (parental discretion). You can contact Naumkeag at 413-298-3239 to learn more about house tours and events.

For more traditional fun, the Stockbridge Chamber of Commerce will host the annual Halloween Parade & Party on October 27. Those looking to participate in the parade should gather in costume at Main & Pine Streets prior to 6 p.m. ready to march up Main Street to the Town Offices where cider and donuts will be served. This event is open to area children and their families. In case of rain, all activities will take place at the library.

Immediately following the Halloween Parade, the Stockbridge Library Association will host the 7th Annual Pumpkin Walk-About in the Stockbridge Library gardens. If you are carving a jack-o-lantern, drop it off at the Library between 5:00 & 6:00 p.m. When you come back after the parade the path will be lit by all the pumpkins carved by local businesses, your neighbors, and you! There will also be some spooky stories and a Halloween treat.

Come out and join in the traditions, both old and new in this quintessential New England town!

Nearby, in the postcard-pretty town of Stockbridge — birthplace of Arlo Guthrie’s “Alice’s Restaurant” — the Norman Rockwell Museum is marking its centenary of the artist’s first Saturday Evening Post cover. From 1916’s “Boy with Baby Carriage” comes “Build a Better Baby Carriage,” a kicky show of contemporary sculpture on its lush grounds. Then duck inside “the room where it happened”: Rockwell’s own, perfectly preserved studio.

See why the NY Post tells you to head to the Berkshires.