Stockbridge Main Street at the holidays

Stockbridge celebrates the holidays with wreaths and festive lights and activities for all ages — live performances, holiday markets, Winterlights and more.

Festivities open on Friday evening, and on Sunday the town reenacts the spirit of Norman Rockwell’s holiday scene Stockbridge Main Street at Christmas, with vintage automobiles parked in the spots occupied in the painting.

Saturday December 7

Historic Holiday Property Tour — 11 a.m. to 3 p.m. Local historic properties will deck their halls for the holidays, for a self-guided tour — the Inn at Stockbridge, The Merwin House with special treats, Ventfort Hall Mansion and Gilded Age Museum with holiday music, High Lawn Farm Museum and Chesterwood and more. This is a ticketed event, and space is likited.

Olga Dunn Dance Company performance of The Nutcracker Seedling — 2:30 p.m. and 3:30 p.m., presented by the Stockbridge Library, Museum & Archives held at the library. Free Admission but Reservation Tickets are Required as seats are limited.

Stockbridge Main Street at Christmas Holiday Concert and Group Sing-Along — 5 to 6:15 p.m. located at the First Congregational Church Stockbridge. Celebrate the magic of the season with a classical lite musical program and group sing-along featuring The Berkshire Bach Players.

Winterlights at Naumkeag — This holiday season the garden sparkles with thousands of shimmering holiday lights.

For Friday and Sunday events, see the daily calendar listings.

2024 more holiday activities around town

Winter Family Fun Day and Nutcracker Collection Display presented by the Stockbridge Library, Museum & Archives held at the library, 10 a.m. to 2 p.m., Free Admission. All day long the library will have a craft table available where children can decorate a snowflake, indoor winter games and a scavenger hunt, and an outdoor StoryWalk© and decorated gardens that you can walk through. At 10:45 a.m. there will be a winter-themed storytime with the youth librarian.

Winter Wonderland Walkway sponsored by the Stockbridge Chamber of Commerce, December 7 to 31 — All are invited to take a stroll through the Winter Wonderland Walkway of decorated trees at the Stockbridge Library.

Holiday Marketplace and Gallery of Wreaths at Berkshire Botanical Garden — December 6 to 8, the annual Holiday Marketplace returns with wreathes and evergreens, garlands and artisans. Free Admission.

The Women’s Service League of the First Congregational Church Holly Fair Saturday, December 7 from 10 a.m.to 1 p.m., First Congregational Church, 4 Main St., with hand-made crafts, gifts and decorations, holiday greens, baked goods, Tea Room, Grandma’s Attic, Santa Claus, silent auction cross-stitch and more. All proceeds to help the community. Free Admission.

Norman Rockwell Museum — The museum has also newly opened Anita Kunz: Original Sisters, Portraits of Tenacity and Courage and Norman Rockwell: Home for the Holidays and The Light that Shines: Norman Rockwell and the Edison Mazda Paintings. December 7 and 8, the museum will lead Norman Rockwell’s Life and Holiday Art guided tours.

Nightwood — The Mount will present the fourth year of an innovative sound and light experience that immerses visitors in a fantastical winter landscape, with scenic elements, theatrical lighting and a dramatic score.

A Christmas Carol — December 6 to 8 and onward, Berkshire Theatre Group offers their annual retelling of the spirits of Christmas eve as they challenge Ebenezer Scrooge, the miser who faces his own bleak past and searches for liht. On a winter night in Victorian England, experience Charles Dickens’ story filled with holiday carols and the wonder of the season.