THE 37th ANNUAL

STOCKBRIDGE MAIN STREET AT CHRISTMAS

December 5 – 6, 2026

Rediscover the magic of the holidays in Stockbridge, where a classic New England village sparkles with twinkling lights, festive wreaths, and timeless charm. This beloved Berkshire destination offers a full weekend of family-friendly experiences designed to create lasting memories.
Enjoy live performances, historic property tours, holiday markets, and the enchanting Winterlights display. Stroll through distinctive local shops, dine at inviting restaurants, and keep an eye out for Santa as he makes a cheerful appearance.
The celebration culminates on Sunday with a beloved tradition inspired by Norman Rockwell’s iconic painting Home for Christmas, a nostalgic portrayal of small-town holiday life. First begun in 1956 and completed in 1967, Rockwell’s image continues to reflect the enduring character of Stockbridge—carefully preserved by generations of residents.
Celebrate the warmth, beauty, and community spirit that define the season in Stockbridge—where the holidays feel just as they should.

TICKETS ARE NOW ON SALE:
We cannot accommodate a change in tickets. Tickets are non-refundable and non-transferable. Please review the event information pages before purchasing and review the number of tickets in your cart before accepting. If you change your order before checking out, make sure to click “Update Cart” before proceeding to checkout.

SATURDAY, DECEMBER 5, 2026

Historic Holiday Property Tour~ 11:00am-3:00pm
Step into the magic of the season with a self-guided holiday tour of Stockbridge’s most treasured historic properties. Explore the beautifully decorated Merwin House and Tappan House at Tanglewood, each offering festive décor and seasonal refreshments. Enjoy holiday music amid the Gilded Age splendor of Ventfort Hall Mansion & Gilded Age Museum, festive music and complimentary gingerbread cookie decorating at The Inn at Stockbridge, and the holiday charm of Chesterwood, beautifully decorated for the season.

Discover the unique history, architecture, and festive traditions of these remarkable properties at your own pace while experiencing the timeless beauty of the Berkshires during the holidays.

Tickets are $35.00 per person. PURCHASE TICKETS

Stockbridge Main Street at Christmas Holiday Concert and Group Sing-Along ~ 5:00 – 6:15pm
The musical high point of the weekend takes place on Saturday evening at the First Congregational Church with a festive holiday concert and joyful community sing-along. Returning for their second year we welcome the Cantantes Pro Musica, the acclaimed chamber ensemble of Albany Pro Musica. This special performance blends beautiful choral music with spirited audience participation. Join voices with friends and neighbors as beloved holiday songs fill the historic sanctuary.

General Admission Seating. Tickets are $40.00 per person. PURCHASE TICKETS

SUNDAY, DECEMBER 6, 2026

Stockbridge Main Street at Christmas Recreation ~ 12 Noon-2:00pm
The weekend culminates on Sunday with Stockbridge’s beloved Main Street at Christmas Recreation, inspired by Norman Rockwell’s iconic painting Home for Christmas. With Main Street closed to traffic, more than 25 vintage automobiles line the street, recreating the charm of a bygone era (weather permitted). A beautifully decorated Christmas tree fills the oversized window of Rockwell’s former studio, while Victorian carolers and students from Monument Mountain Regional High School provide festive entertainment.
Families can enjoy Roger the Jester, fire truck discoveries, children’s crafts, and visits with Santa and Mrs. Claus and their reindeer sheep. Stroll along Main Street, browse local shops and the Norman Rockwell Museum pop-up shop, and enjoy seasonal food and beverages at El Nopal Mexican Cuisine and the Red Lion Inn’s pop-up courtyard booth.
This heartwarming tradition offers a wonderful way to celebrate the holiday season and experience the timeless charm of Stockbridge. Admission: $5 per person (includes commemorative button while supplies last) | Children under 12: Free PURCHASE TICKETS

Horse-drawn wagon rides by Clay Hill Farm will also be available for an additional fee (weather permitting; heavy rain cancels rides).

There are parking restrictions on Sunday for the Recreation, please refer to Parking & Directions for details.
Click Here for Parking & Directions

We invite antique car owners to be part of this cherished tradition by showcasing their vehicles during Sunday’s recreation. Advance registration is needed. Click Here for Details.