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 inside the magic of the season with this self-guided tour of some of Stockbridge’s most treasured historic properties. Explore the beautifully decorated Merwin House, where festive décor and seasonal refreshments await, then enjoy holiday music amid the Gilded Age splendor of Ventfort Hall Mansion & Gilded Age Museum.
The tour also includes The Inn at Stockbridge, Chesterwood, and the Tappan House at Tanglewood, each offering its own unique blend of history, architecture, and holiday charm. Experience these remarkable destinations at your own pace while celebrating the beauty and traditions of the Berkshires during the holiday season.
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
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.

With the street closed to traffic, more than 25 vintage automobiles line Main Street, creating a picture-perfect backdrop. A beautifully decorated Christmas tree fills the oversized window of Rockwell’s former studio, while Victorian Carolers and talented students from Monument Mountain Regional High School provide festive entertainment. Families can enjoy Roger the Jester, fire truck discovery, face painting, horse-drawn wagon rides, children’s crafts, and visits with Santa & Mrs. Claus and their reindeer sheep. Be sure to allow time to stroll along Main Street, browse the quaint shops and Norman Rockwell Museum pop-up shop, and enjoy a meal at one of the area’s welcoming restaurants and the Red Lion Inn pop-up courtyard booth offering seasonal food and beverages with fires to warm by.

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.