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What's Happening · October 26, 2026

What's Happening in the Berkshires: Local Flavor & Fall Outings

Explore cooking classes, a clarinet-focused season opener, and a film at the Triplex—plus extended transit service and a chance to help shape Sheffield’s future.

Arts, music & culture

Looking for a cultural outing? Check the schedule for Close Encounters With Music’s season opener at the Mahaiwe. The clarinet takes center stage in a program exploring how composers have used its distinctive voice across musical periods and styles.

At the Triplex, “You Can See Everything” blends a detective story with a character study and a look at how the media turns complicated lives into consumable scandals. Confirm performance dates and showtimes before heading out.

Food, drink & new businesses

For a hands-on way to connect with local food, explore Heart & Soil Collective’s cooking classes. These farm-to-table gatherings bring people together to learn cooking skills, prepare a locally grown meal, and share it around the table. Check upcoming class availability before making plans.

Community news to know

Getting around South County gets a boost this week: the South County Connector returns to extended weekday service starting October 26. Great Barrington is also working toward restoring weekend transportation and the Pittsfield FLEX route, but those services are not yet back.

Sheffield residents can help guide the town’s future through its planning survey. It’s an opportunity to share what you love, what needs improvement, and what should matter most in long-term planning.

Residents are seeking answers about the rail transportation plan for Housatonic River remediation, with protesters pushing back against the cleanup project. Another local reminder asks everyone to keep construction debris out of roadsides and woods rather than leaving others to handle the cleanup.

Relocation tip from the team

Moving to or from the Berkshires? Build your home search around your everyday routine—not just the property. Check the trips you’ll make for work, groceries, healthcare, and family visits, and verify transportation options before relying on them. The Real Harmony & Associates team can help you think through those practical questions, whether your next chapter is local or farther down the East Coast.

Thinking about a move in the Berkshires?

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Harmony Edwards

Team Lead, REALTOR®, Real Harmony & Associates

This weekly events roundup was written with AI assistance from the linked local news sources. Visit each source for full details.