Antique Car Owners Get to Show Off Their Vehicles in the Berkshires This December

One of the many things I love about the Berkshires is that no matter what the season, Berkshire County is always beautiful. Sure, the fall foliage is quite the treat, but the Berkshires shine in winter, spring, summer, and fall. From the beautiful rivers and waterfalls to the freshly fallen snow, the Berkshires are always beautiful.

I especially love the Berkshires in late fall/early winter season. The transition from leaves to snow makes the county feel comforting and inviting. Another aspect that supports this atmosphere is the celebratory events that the towns host. For example, the Holiday Stroll in Great Barrington usually takes place on the second Saturday in December and fills Main and Railroad Streets with holiday festivities. The same is true of the December Holiday Walk in Williamstown. Many Berkshire towns host their own celebrations to help keep that atmosphere and beauty beaming throughout the county.

The Town of Stockbridge Has Been Known for a Big Beautiful Celebration for Over 30 Years

Another town that is known for celebrating Berkshire beauty in fall/winter and has travelers coming from all over to savor the experience is Stockbridge with the Annual Stockbridge Main Street at Christmas holiday weekend celebration. The 37th annual event will take place this year in downtown Stockbridge on December 5 and 6.

READ MORE: Berkshire Residents Can Visit Spirit Christmas This Year Without Having to Drive Hours Out of the County

Stockbridge Wants to Display Your Antique Vehicle

The Town of Stockbridge and the Stockbridge Chamber of Commerce are seeking your antique vehicle. That's right. If you own an antique vehicle and would like to register it to be part of the Sunday, December 6 recreation of the classic Norman Rockwell painting on Main Street in Stockbridge, you can. Can you imagine thousands of people looking at your vehicle in awe all while being part of this iconic recreation? Talk about something to be proud of.

READ MORE: Berkshire County Had a Great Night for a Car Show; Look at These Beauties (photos)

Sign Up Details

The Stockbridge Chamber of Commerce is seeking 55 vehicles, especially from the 1940s and 1950s, for the event but will include others in designated parking locations. If you want yours on display that day, don't snooze; sign up now. The registration deadline is November 15, 2026. You can find all of the registration details here. Get your vehicle shined up and ready to go this December in downtown Stockbridge.