Historic Property Tours, Holiday Concert and Main Street Reenactment

October 15, 2026 — Stockbridge, MA — The Stockbridge Chamber of Commerce is seeking volunteers for the 37th Annual Stockbridge Main Street at Christmas, taking place December 5–6, 2026. This beloved holiday tradition features historic property tours, a holiday concert, and the live recreation of Norman Rockwell’s iconic Stockbridge Main Street at Christmas painting.

Volunteers play an important role in making this special weekend possible, and several opportunities are available.

HISTORIC PROPERTY TOUR — SATURDAY, DECEMBER 5

The Historic Property Tour is a popular highlight of the weekend, offering visitors a chance to experience some of the area’s distinctive historic properties. This year’s tour includes Merwin House, Chesterwood, the Inn at Stockbridge, the Tappan House at Tanglewood, and Ventfort Hall Mansion and Gilded Age Museum.

We need at least two volunteers per shift at each location. Shifts are scheduled for 10:30 a.m.–1:00 p.m. and 1:00–3:30 p.m.

Volunteers will work alongside property owners, greeting visitors, helping manage visitor flow, and providing an extra presence at each site. No tour-guiding experience is necessary. As a thank-you, volunteers will receive a complimentary ticket to visit the other participating properties before or after their shift.

When responding, please provide your mailing address, phone number, and email address, along with your preferred shift. Please also let us know if you are flexible about your assigned property or shift.

HOLIDAY CONCERT — SATURDAY, DECEMBER 5

First Congregational Church | 4:15–6:30 p.m.

Volunteers are needed to check tickets, distribute concert programs, and assist with closing after the performance. Volunteers will also have the opportunity to enjoy the concert.

SUNDAY TICKET/BUTTON STATION — DECEMBER 6

10:00 a.m.–2:00 p.m.

Volunteers are needed to verify tickets and distribute event buttons at the outdoor ticket station during Sunday’s Main Street celebration.

PLEASE VOLUNTEER BY NOVEMBER 1

If you are available to help, please contact the Stockbridge Chamber of Commerce at 413-298-5200 or info@stockbridgechamber.org. Please indicate which volunteer opportunity interests you and your availability.

Your time and support help the Chamber continue this cherished Stockbridge holiday tradition. Gather a friend, lend a hand, and be part of a festive weekend celebrating our historic New England village.

For additional event details, visit www.stockbridgechamber.org.