Berkshire Daily: Stockbridge Homes, Mahaiwe Music & Transit Updates

Real estate & housing

This week’s property coverage features a six-acre Stockbridge retreat with contemporary architecture, privacy, and views, presented by Leslie Chesloff of William Pitt Sotheby’s International Realty’s Great Barrington Brokerage.

The October 23 real estate sales roundup also covers transactions across Berkshire County, Massachusetts; Litchfield County, Connecticut; and Columbia County, New York.

• 6-Acre Stockbridge Retreat: Contemporary Luxury with Views · The Berkshire Edge
• Berkshire region real estate sales – October 23, 2026 · The Berkshire Edge

Local events

Close Encounters With Music opens its season at the Mahaiwe with a clarinet-centered program exploring how composers have used the instrument’s distinctive sound 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 media turns complicated lives into scandal-driven content. Meanwhile, a recap of the inaugural Stockbridge Film Festival looks back on 56 films from around the world, shown October 16–18.

• PREVIEW: Close Encounters With Music opens season with clarinet-centered program at Mahaiwe · The Berkshire Edge
• AT THE TRIPLEX: The elusive truth of ‘You Can See Everything’ · The Berkshire Edge
• Stockbridge Film Festival brings filmmakers and films to town · The Berkshire Edge

Notable local news

The South County Connector returns to extended weekday service tomorrow, October 26. Great Barrington is also working toward restoring weekend transportation and the Pittsfield FLEX route, with both anticipated in the coming weeks as operations allow.

Sheffield residents have an opportunity to help guide the town’s future through a planning survey about what they value, what needs improvement, and their priorities for the years ahead.

Residents are seeking answers about the rail transportation plan for Housatonic River remediation, with protesters pushing back against the cleanup project. A separate commentary urges proper disposal of construction debris rather than leaving it along roads or in woods for others to clean up.

• South County Connector returns to extended weekday service starting Oct. 26 · The Berkshire Edge
• Help shape Sheffield’s future by taking the town’s planning survey · The Berkshire Edge
• Berkshire residents seek answers for Housatonic River remediation rail transportation plan · The Berkshire Edge
• Keep construction waste out of our woods · The Berkshire Edge

Relocation tip from the team

Before moving to or from the Berkshires, make a checklist of your everyday travel needs: work, groceries, appointments, and visits with loved ones. Check current transportation options directly with providers, and use those routines to guide your home search.