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 November 30, December 1 & 2, 2018.

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 include horse drawn rides, a visit from Santa, Roger the Jester, lunch at the Christmas Food Booth and much more.

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 ambiance which draws so many visitors.

2021 Calendar To Be Announced

This was the 2018 Sechedule

FRIDAY, NOVEMBER 30, 2018

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.

SATURDAY, DECEMBER 1, 2018

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.  Tickets are $20.00 per person. This years featured properties are Naumkeag, Whitney House, Windermere, Applegate Inn, Devonfield Inn, National Shrine of the Divine Mercy and High Lawn Farm Museum.

Children’s Holiday Sing Along ~ 11:00-11:30am Join special guest Julie Stepanek for 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 Celebrate the magic of the season with a joyful holiday musical program by the Berkshire Lyric and the Blafield Children’s Chorus held at the First Congregational Church.  Tickets are $25.00 per person. General Admission Seating. 

SUNDAY, DECEMBER 2, 2018

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 lunch at the Christmas Food Booth sponsored by the Red Lion Inn. Take 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.  Children may create holiday fun at Santa’s workshop sponsored by the Norman Rockwell Museum and have their face 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. Horse drawn wagon rides by Clay Hill Farm will also be available for an additional fee.