STOCKBRIDGE MAIN STREET AT CHRISTMAS – DECEMBER 6-7, 2025

36th  ANNUAL NORMAN ROCKWELL HOLIDAY CELEBRATION

DECEMBER 6-7, 2025

Rediscover the joys of the holidays in Stockbridge, MA, where the town transforms into a magical New England village, adorned with twinkling lights and charming holiday wreaths that evoke the spirit of the season. This enchanting destination offers a delightful array of family-friendly activities that promise to create cherished memories for all. From captivating live performances and historic property tours to bustling holiday markets and the mesmerizing Winterlights display, there’s truly something for everyone to enjoy. Don’t miss the Rockwell Holidays at the Museum, where art and tradition come alive, or the unique shops and restaurants that showcase the best of local commerce. And of course, Santa himself will be making appearances, adding an extra sprinkle of joy to this festive season. Join us in celebrating the warmth and community spirit that makes Stockbridge a quintessential holiday experience, where every moment spent here is sure to inspire and delight!

On the first weekend in December each year the town pays homage to Norman Rockwell’s idyllic depiction of village life during the holidays, Stockbridge Main Street at Christmas.

One of the highlights is the much-anticipated historic property tours on Saturday. This year’s self-guided journey invites you to explore The Merwin House, where special treats await, and to bask in the joyous holiday music at Ventfort Hall Mansion and Gilded Age Museum. Don’t miss the serene beauty of the National Shrine of Divine Mercy Residence and the creativity and inspiration of Chesterwood, each location brimming with festive cheer.

The musical high point of the weekend takes place on Saturday evening at the First Congregational Church featuring a brand-new show by the Albany Pro Musica Chamber Singers, followed by a spirited group sing-along that promises to unite us all in joyous celebration.

As the weekend culminates on Sunday, Stockbridge comes alive with a heartwarming reenactment that beautifully embodies the spirit of Norman Rockwell’s iconic holiday scene, “Home for Christmas.” Just a stone’s throw from the Norman Rockwell Museum, where the original painting resides, this festive celebration transforms Main Street into a vibrant tapestry of holiday cheer. Visitors will be delighted by the sight of over 25 vintage automobiles lined up along the street, which is joyfully closed to traffic. At the center, an enchanting Christmas tree fills the oversized window of Rockwell’s former studio, creating a picturesque backdrop. The festivities include captivating performances by the Victorian Carolers, and talented students from Monument Mountain Regional High School, alongside delightful horse-drawn rides, engaging children’s crafts, and magical visits with Santa himself. As you stroll along the street, take a moment to explore the quaint shops and inviting restaurants.

“If it’s possible to be homesick for a place you’ve never lived in, it’s most likely to happen in Stockbridge, MA during their Main Street at Christmas annual events.” Chris Bury for ABC’s Good Morning America.

It’s such a magical time of year to enjoy with family and friends. Be sure to book your tickets and stay in advance.

Calendar Listing

SATURDAY, DECEMBER 6, 2025

Historic Holiday Property Tour ~ 11:00am-3:00pm This year’s self-guided journey invites you to explore The Merwin House, where special treats await, and to bask in the joyous holiday music at Ventfort Hall Mansion and Gilded Age Museum. Don’t miss the serene beauty of the National Shrine of Divine Mercy Residence and the creativity and inspiration of Chesterwood, each location brimming with festive cheer. Tickets are $30.00 per person.

A BRAND NEW PERFORMANCE & PROGRAM! Stockbridge Main Street at Christmas Holiday Concert and Group Sing-Along ~ 5:00 – 6:15pm located at the First Congregational Church Stockbridge. Celebrate the magic of the season with Albany Pro Musica Chamber Singers followed by a spirited group sing-along. General Admission Seating. Tickets are $40.00 per person

SUNDAY, DECEMBER 7, 2025

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 25 antique cars parked along the street (weather permitting) and a full range of festive activities to delight the child in everyone. Shop for special Rockwell gifts at the Norman Rockwell Museum Pop-up Shop. Hear holiday music by the Victorian Carolers and the talented students from Monument Mountain Regional High School. Savor food and seasonal beverages at the Red Lion Inn courtyard pop-up and Great Cape Baking Co. food booth. Children may have their face painted and enjoy Stories & Crafts and magical visits with Santa, Mrs. Claus & their Reindeer sheep. Tickets are $5.00 per person with Children under 12 Free.  Horse drawn wagon rides by Clay Hill Farm will also be available for an additional fee on the day of (heavy rain will cancel rides.)

To Order Tickets: Tickets may only be purchased in advance online through the Stockbridge Chamber of Website: www.stockbridgechamber.org

PARKING

Please note that on Sunday there is no parking on Main Street to 2pm.  On Street Parking is available West & East of Main Street block where marked and at Marians on Eden Hill parking lot, 2 Prospect Hill Road. A shuttle service is available at the Eden Hill Parking Lot from 11:00am to 2:30pm.