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 TO EVENTS WILL GO ON SALE IN SEPTEMBER:
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 inside the season with this self-guided tour of some of Stockbridge’s most treasured historic properties. Visit the charming Merwin House, where festive décor and seasonal treats welcome guests, and enjoy joyful holiday music at Ventfort Hall Mansion and Gilded Age Museum.
The tour also includes Chesterwood and the Tappan House at Tanglewood, offering a unique blend of history, architecture, and holiday spirit throughout the Berkshires. A perfect way to experience the elegance and charm of the season at your own pace. Tickets TBA.
Stockbridge Main Street at Christmas Holiday Concert and Group Sing-Along ~ 5:00 – 6:15pm Celebrate the spirit of the season at the First Congregational Church in Stockbridge with a festive holiday concert and joyful community sing-along.
Featuring 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 TBA
SUNDAY, DECEMBER 6, 2026
Stockbridge Main Street at Christmas Recreation ~ 12 Noon-2:00pm
Step into a living holiday postcard in Stockbridge, where Main Street is transformed into the scene that inspired Norman Rockwell’s iconic Stockbridge Main Street at Christmas.
More than 25 antique cars (weather permitting) line the street, recreating the charm of a bygone era, while festive activities bring the season to life for all ages. Browse special finds at the Norman Rockwell Museum
pop-up shop, enjoy holiday music, and savor seasonal food and beverages in the courtyard of the Red Lion Inn.
Children can delight in face painting, story time and crafts, and magical visits with Santa, Mrs. Claus, and their charming “reindeer” sheep.
Horse-drawn wagon rides by Clay Hill Farm will also be available for an additional fee (weather permitting; heavy rain cancels rides).
Admission: $5 per person (includes commemorative button while supplies last) | Children under 12: Free
There are parking restrictions on Sunday for the Recreation, please refer to Parking & Directions for details.
Click Here for Parking & Directions
Antique Car Owners Click Here for Details. Advanced registration is needed.
