Visit Stockbridge Massachusetts

10/21/2026

Kate Kortum Quartet Plays the Indigo Room
October 24 | Great Barrington, MA
Jazz singer Kate Kortum brings her quartet to the Mahaiwe’s Indigo Room. The Mahaiwe describes her as combining the intimacy and storytelling of cabaret with classic jazz vocals, and a “knowing, sly playfulness” that gives a distinctly modern female perspective on classic jazz and swing tunes, most written by men generations ago.

10/20/2026

Norman Rockwell Museum Looks at How Black Artists Portray Dignity, Struggle, and Pride
October 23 | Stockbridge, MA
How Black artists have represented the dignity, struggles, and pride of Black Americans is the subject of the “Black Excellence and Everyday Life” talk. The event looks closely at the work of artists like Robert Carter, who used their art to educate and to speak out for political change and social justice.

10/19/2026

Colors are still popping in .

10/18/2026

10/18/2026

🎄 Tickets Are Selling for Stockbridge Main Street at Christmas! 🎄

Don’t miss the magic of the 37th Annual Stockbridge Main Street at Christmas, December 5–6, 2026! Historic Property Tours, Holiday Concert, Main Street Recreation.

Experience the charm of our quintessential New England village transformed into a festive recreation of Norman Rockwell’s beloved Home for Christmas painting.

✨ Holiday traditions, festive activities, and small-town charm await!

🎟️ Get your tickets while they last! www.mainstreetatchristmas.com

10/17/2026

🍁 The fall foliage is beautiful in ! 🍂 Come visit, take in the spectacular autumn colors, explore our charming New England village, and enjoy the beauty of the Berkshires before the leaves are gone!

Make time for a fall getaway—you won’t want to miss it! ❤️

10/16/2026

Fresh voices and kinetic movement Jacob's Pillow
Experience the Doris Duke Theatre in the fall with two weekends of performances. For something new, witness today's emerging choreographers as they present world premieres created for Youth America Grand Prix's inaugural choreographic fellowship. Or, celebrate the 40th anniversary of Doug Varone and Dancers with their emotionally resonant program.
Youth America Grand Prix: Fresh Voices in Dance | October 16-18
Doug Varone and Dancers October 23-25

10/16/2026

What sparks your curiosity?
Single tickets & passes are now on sale for field Lenox, October 23–25 right here at .
From artist Maira Kalman exploring the power of joy, Pulitzer Prize-winning biographer and historian Kai Bird who delves into truth about power, acclaimed novelist Colm Tóibín on the creative process, and Carol Gilligan, pioneering psychologist and author of In a Different Voice, asks what happens when we mistake women’s silence for consent – field brings together remarkable thinkers, writers, artists, and experts for a weekend of ideas, discovery, and conversation across disciplines.

Whether you're drawn to literature, history, psychology, health, or the unexpected connections between them, you can now choose the sessions that interest you most. Join us for conversations that challenge assumptions, open new perspectives, and invite us to listen, stay curious, and hear the other side.

10/16/2026

The Stockbridge Halloween Parade and Pumpkin Walk will take place on Friday, October 30, 2026 for area children. Marchers will meet at the corner of Main & Pine Street at 6:00 p.m. and march up Main Street to the front lawn of the Stockbridge Library for c***r & donuts, and pumpkin walk-about with Jack-O-Lanterns carved by local businesses and area children. The fire truck will be stationed for discovery. A Halloween story time will take place at 6:30PM and Drop-in Halloween crafts inside the library from 6:00-7:30 p.m.

Children and businesses interested in showcasing a Jack-O-Lantern of their own, should drop them off at the library any time before 5:30 p.m. (The library staff will light them and provide candles). You can take them home at the end of the evening.

In case of rain the parade is cancelled, and activities will take place in the library.

These events are sponsored by the Stockbridge Chamber of Commerce, Stockbridge Library, Stockbridge Police & Fire Departments, and Stockbridge Coffee & Tea.

10/15/2026

THE MET: LIVE IN HD
Macbeth
Saturday, October 17, 1 pm
Manton Research Center auditorium
Following past triumphs in many of Verdi’s signature baritone roles, Quinn Kelsey is the Scottish king haunted by the ghosts of his murderous ascent to the throne, opposite Lise Davidsen—the world’s reigning dramatic soprano—as the power-mad Lady Macbeth, whose ruinous ambition damns them both.
3 hours, 30 minutes
The Met: Live in HD is the Metropolitan Opera’s award-winning series of live high-definition cinema simulcasts. Simulcasts feature the full performance along with backstage interviews and commentary.