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. Plan your stay with us!

A Norman Rockwell Holiday 

December 6 - 7, 2025 

Stockbridge, MA

Advance orders are recommended as tickets to all events are limited, sell out fast and NO tickets will be sold on site of events.

BUY TICKETS!

Photographs: Santa: In loving memory of Larry Bayles, Copyright Joel Lanio

Horses: Credit Blue Moon Designs

Norman Rockwell's illustration: "Santa and His Helpers" artwork courtesy of the Norman Rockwell Family Agency

The 36th Annual Stockbridge Main Street at Christmas

is generously sponsored by:

WINTERLIGHTS AT NAUMKEAG

December 6 - 7, 2025 

This holiday season the beautiful garden property sparkles with thousands of shimmering, artfully designed holiday lights. Bring the whole family for a magical, fun, outdoor experience – with food, refreshments, and more. This year patrons who purchase tickets to Stockbridge Main Street at Christmas events will receive exclusive pre-sale access to Winterlights tickets on December 6 & 7, prior to them going on sale to the general public. Tickets are purchased directly through the Trustees. Follow the link provide on the calendar of events.