Norman Rockwell Home For Christmas detail

The holidays are just around the corner and there may be no better way to celebrate them than at Stockbridge Main Street at Christmas 2020. The event is a little different this year, as I am sure you can imagine, but still includes a wide variety of fun and festive attractions. It all kicks off on the weekend of December 4th, 2020 in Stockbridge, MA.

Norman Rockwell spent the last 25 years of his life right here in Stockbridge, MA. Rockwell was an artist who worked from life. Consequently, many bits and pieces of the world around him ended up in his illustrations. This is definitely true of our quaint, New England village, and especially evident in his 1967 “Home For Christmas” painting.

“Home For Christmas” depicts an early winter evening along Main Street in Stockbridge. People are shopping, children playing, vintage cars line the street, and the icy street is bathed in the warm, golden light of the shop windows. Rockwell’s own studio window, seen above the brightly lit market, is dark but for a large, decorated Christmas tree.

Times have changed a lot since Rockwell painted this famous image – yet Main Street in Stockbridge remains almost as it was. This was the inspiration behind the annual Main Street at Christmas event. A life-size recreation of Rockwell’s “Home For Christmas” on Main Street, complete with vintage cars, costumes, and so much more.

While the ongoing pandemic won’t allow us to do that this year, there are still a host of festive holiday events and activities to attend. Best of all, the location of our Berkshires B&B, The Inn at Stockbridge, puts you less than five minutes drive from all the fun and excitement!

Stockbridge Main Street at Christmas 2020

Stockbridge Main Street at Christmas 2020

This year’s celebration includes a variety of virtual, outdoor, and masked and socially distanced events. Just look!

Stockbridge Main Street at Christmas Dec 4th – 31st
A free online video of over 30 years of Main Street at Christmas celebrations. This video will be available to view through December 31st, 2020. Learn more.

Holidays at the Norman Rockwell Museum
The Norman Rockwell Museum continues its holiday tradition of recreating a miniature Stockbridge winter village, complete with toy train. You can also view the original “Home For The Holidays,” painting that started it all – and much more.

Holiday Concert Dec 4th – 31st
A free online video mix of Holiday Concerts Past. This video will be available to view through December 31st, 2020. Learn more.

Winter Wonderland Walkway Dec 4th – 31st
Enjoy a free stroll through the light bedecked Holiday Tree walkway at the Stockbridge Library. Masks and social distancing required.

Holiday Memories – Nov 20th – Dec 20th
Bundle up for a holiday show in the Berkshire Theatre Group’s outdoor Unicorn Theatre. “Holiday Memories” is Truman Capote’s captivating recollection of his depression-era Alabama childhood and friendship with his cousin, Sook. More information.

Stockbridge Main Street at Christmas 2020

Winterlights at Naumkeag – Nov 27th – Jan 2nd
Enter a wonderland of twinkling lights and fantastic landscaping with a visit to Naumkeag’s annual, outdoor Winterlights event. The fun and safe outdoor experience includes food, refreshments, and more. Tickets and more information.

NightWood at The Mount – Nov 19th – Jan 3rd
Visit Edith Wharton’s The Mount and see the property transformed into a fantastical winter landscape for the holidays: NightWood. The opening night gala on November 19 includes a pop-up bistro dinner, fire pits, seasonal cocktails, and a food truck. Learn more at

And That’s Not All

The above is just a small handful of all the events and attractions that surround Stockbridge Main Street at Christmas 2020. Visit for a complete list of 2020 holiday events.