Berkshire Daily: Stockbridge Homes, Lee Festivities & Transit Updates

Real estate & housing

This week’s property coverage features a six-acre contemporary retreat in Stockbridge, with views and privacy highlighted in the listing 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

Lee is marking its 249th anniversary while beginning a year of festivities leading toward its 250th. The planned events and activities are intended to bring the community together.

Coming up October 29 through November 1, Tanglewood Learning Institute’s “Close to Home” series will bring student musicians, Berkshire jazz artists, former Boston Symphony Orchestra players, and young choreographers together for classical music, jazz, and dance.

In a look back at the local arts calendar, Stockbridge’s inaugural film festival ran October 16–18 and featured 56 films from around the world, bringing both films and filmmakers to town.

• Lee embarks on 250th anniversary festivities by marking its 249th anniversary · The Berkshire Edge
• PREVIEW: Tanglewood Learning Institute’s ‘Close to Home’ series spotlights Berkshire musicians, students, and dancers Oct. 29 through Nov. 1 · The Berkshire Edge
• Stockbridge Film Festival brings filmmakers and films to town · The Berkshire Edge

Notable local news

The South County Connector is set to return to extended weekday service on October 26. Great Barrington is also working toward restoring weekend transportation and the Pittsfield FLEX route, though those returns remain dependent on operational readiness.

Sheffield residents have an opportunity to help guide the town’s future through its planning survey. The survey invites input on what residents value, what they would like improved, and their priorities for town planning.

Residents are also seeking answers about the rail transportation plan associated with Housatonic River remediation. An event on the issue drew protesters pushing back against the cleanup project.

• 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

Relocation tip from the team

Before moving to or from the Berkshires, map out your everyday routines—not just your commute. Check current transportation options, visit prospective neighborhoods during your usual travel times, and consider how you will reach groceries, appointments, and favorite activities. Share those priorities with your real estate team as you narrow your search.