December 4, 5 & 6, 2020

FULL Details and Events coming in April 2020

The town of Stockbridge, made famous by Norman Rockwell’s painting of the village during the holidays, becomes a magical New England setting decorated with holiday wreaths and festive lights, as the town celebrates Stockbridge Main Street at Christmas December 6, 7 & 8, 2019.

Sponsored by the Stockbridge Chamber of Commerce, the holiday celebration offers a full range of activities, with highlights including holiday readings, house tours, caroling, and a holiday concert.

Capping off the weekend is a recreation on Sunday of the scene depicted in Main Street at Christmas, complete with vintage automobiles parked in the spots occupied in the painting. The day’s activities are sure to delight the the child in everyone.

The festivities celebrate Rockwell’s popular depiction of what for many is the quintessential small New England Town, with all the longing for a simpler time that it represents. Rockwell began painting the popular image in 1956, but did not complete it until December 1967.

The image and character of Stockbridge has changed little over the years, thanks to the great care and affection of its residents, and it is that special ambience which draws so many.

2020 Calendar Coming in April

FRIDAY, December 6, 2019

Readings Around The Hearth ~ 5:00-6:30pm Gather ’round to hear classic stories of the season presented by the Stockbridge Library, Museum & Archives held at the library.  Free Admission.


Holiday House Tour ~ 11:00am-4:00pm Visit some of the area’s Historic Properties, Inns and Private Homes. This self-guided tour is one of our most popular events. Highlights of this years tour will be the Stockbridge Country Inn, Old Corner House, Naumkeag, Seven Hills Inn, the Kniffen House, West Stockbridge Congregational Church, West Stockbridge Historical Society. Tickets are $20.00 per person.

Children’s Holiday Sing Along ~ 11:00-11:30am  Enjoy a fun winter themed sing along at the Stockbridge Library, Museum & Archives. Free admission.

Caroling & Luminaria Walk ~ 6:00-7:00pm Meet in front of The Red Lion Inn, Main Street with your candle or flashlight and join the festive caroling followed by a Luminaria walk to the First Congregational Church.

Holiday Concert ~ 7:30pm  Exciting New Performers! Celebrate the magic of the season with a joyful holiday musical program featuring Winter Song, an instrumental ensemble led by Joe Rose with singers Beth Rose and John Demler. Also singing will be a women’s group from Simon’s Rock College, led by Berkshire Lyric’s long-time director Jack Brown. The event is held at the First Congregational Church of Stockbridge. General Admission Seating.  Concert is Sold Out!  There are no tickets available at the Red Lion Inn or at the Church the evening of the concert. There is no waiting list.  If you missed tickets for the concert, you may be interested in going to WinterLights at Naumkeag. For more information and tickets click here.


Stockbridge Main Street at Christmas Recreation ~ 12 Noon-2:00pm See Main Street as Norman Rockwell did when he painted the famous Stockbridge Main Street at Christmas. Main Street becomes a magical New England village with over 50 antique cars parked along the street (weather permitting) and a full range of festive activities to delight the child in everyone. Enjoy Roger the Jester and photo ops with Norman Rockwell in a “Triple self portrait” selfie or show your face in a Norman Rockwell painting. Hear holiday music by Monument Mountain Regional High School and the Berkshire Victorian Carolers. Children may create holiday fun at Santa’s workshop sponsored by the Norman Rockwell Museum or have their faces painted. Complete the day with a visit from Santa. Commemorative Buttons offering admittance to Sunday’s Main St. activities are $5.00 per person. Children under 12 free. .  Commemorative Buttons offering admittance to Sunday’s Main St. activities are $5.00 per person. Children under 12 free. Horse drawn wagon rides by Clay Hill Farm will also be available for an additional fee.
There are parking restrictions on Sunday, please refer to Parking & Directions for details.


The weekend events are sponsored in part with generous donations from
The Red Lion Inn

*Photo Credit: Norman Rockwell, Stockbridge Main Street at Christmas. From the Permanent collection, and on view at Norman Rockwell Museum. © 1967, Norman Rockwell Family Agency