Stockbridge Main Street at Christmas | Home for the Holidays

On one December weekend each year, locals and visitors alike step inside a Norman Rockwell painting come to life in Stockbridge, Massachusetts.

They coast into the empty parking spaces like time travelers coming home. A dusting of fresh snow powders the sidewalk in front of the Red Lion Inn in Stockbridge, and the Berkshires do indeed feel “dreamlike on account of that frosting,” as James Taylor sang in 1969. It’s just frosted enough for atmosphere, too; not enough to keep the vintage cars away. A pale turquoise ’55 Studebaker lumbers into place. Here comes an Oldsmobile Rocket 88, with a Christmas wreath dangling from its pug nose. A pristine ’51 Mercury four-door sports sedan looks as though it’s just driven here from the showroom. We watch in silence, this first weekend in December, our frozen breath suspended in the air, as these elegant, multi-ton souvenirs pull into their berths. They’ve driven a long way, 60 years or more, sparking admiration and sometimes wistful memories. It’s beginning to look a lot like 1955 … a Norman Rockwell scene, if ever there was one …

It’s the 24th year that this pretty little village in western Massachusetts has reenacted Norman Rockwell’s iconic Stockbridge Main Street at Christmas painting. Rockwell lived and worked here for the last 25 years of his life, until his death in 1978. The eight-foot-long original painting hangs in the Norman Rockwell Museum, just a few miles outside town, and on this particular weekend it will be visited like a favorite aunt. We’ll all lean in to look at it more closely, maybe tipping forward just the way a Rockwell model would, comparing it with the actual street scene we left just minutes ago. We’ll make careful note of the cars, most of them from the ’40s and ’50s. And then, back in town, capping off a full weekend of caroling, Christmas concerts, house tours, and some serious strolling, we’ll step back in time for two magical hours on Sunday, as Main Street closes to modern traffic and these grand old dames take their places instead. Police Chief Rick Wilcox, 65, supervises the line of demarcation between past and present on Main Street. Earlier in the day, orange traffic cones were strung across the street, blocking traffic from the area Wilcox calls “the Norman Rockwell painting,” running from South Street all the way to Elm Street. Wilcox grew up in town, and after 43 years on the police force, he’ll be retiring in just a few months. “It’s a little bittersweet,” he says. “I’ll miss people. I don’t know that I would have wanted to do police work anywhere but in Stockbridge. My family has been here for generations. Part of my passion for being involved with the town and the police department is deep roots.”

As a boy, Wilcox put on a Boy Scout uniform and modeled for Norman Rockwell, but “ended up on the cutting-room floor,” he smiles ruefully. His older brother, an Eagle Scout, fared better, appearing in three or four paintings. And his grandfather posed for the clerk in Marriage License (but got the hook, too). The standard line, usually delivered with a laugh, is that the artist painted everyone in town during those 25 years. Out on the streets, it’s tempting to size up faces the way Rockwell might have. And just as easy to see how many would look right at home in one of his paintings. “It was a Norman Rockwell childhood in many ways,” Wilcox recalls, of growing up in Stockbridge. “Of course, as you talk to me, I’m probably giving you the Norman Rockwell version.” Which is probably much more apt to happen if the painter is literally weaving in and out of your life. Rockwell’s painting studio was right on Main Street. He lived just around the corner on South Street and was a familiar figure riding his bike through town. “Everybody knew he was a well-known artist,” Wilcox says, “but he was just a neighbor.”

As pretty as the town is, that’s not why Rockwell moved here, though. Fascinated by the process of psychotherapy, he chose Stockbridge so that he and his then-wife, Mary, could be closer to the Austen Riggs Center. It seems that the tall, willowy man Wilcox remembers cycling around town was more complicated than you might guess from the 321 homey covers he so famously painted for the Saturday Evening Post. Knowing that reveals Rockwell in a different light–and makes you think that maybe he had to work harder than we imagined to come up with those comforting, small-town scenes. Equally possible, perhaps he found exactly what he needed in this small, artistic community. And maybe that’s part of what the town tries to re-create, too, when it pays homage to Rockwell and his love of Stockbridge in its yearly reenactment. “It brings the spirit of Christmas in,” says Michele Kotek, innkeeper at the historic Red Lion Inn, which is blazing away with good cheer, as it has for 240 years. “There’s the hustle and bustle of Christmas–shopping and getting organized–and then you come to Stockbridge, to the reenactment, and it makes you stop and go back to that warm-and-fuzzy feeling of how it should be, how Norman Rockwell thought it was, as well.” So let’s be clear: What happens on Main Street isn’t an exact replica of the painting. Rockwell painted 16 cars, but the reenactment “grew from there to have as many antique cars as we could possibly get because people are interested in seeing them,” says Barbara Zanetti, executive director of the local Chamber of Commerce, who’s been doing Stockbridge Christmas for 20 years. And Rockwell himself took some liberties with exactitude. He included the Berkshires in the painting, which are nowhere visible from town. He added a glimpse of his own little house on South Street, on the far-right-hand side of the painting. And he even fiddled with the overall era. Meg Williamson of the Rockwell Museum explains, “This painting was originally commissioned for Hallmark. [Rockwell] didn’t make the deadline, so he put the painting in storage for 10 years, but when McCall’s magazine called, looking for a holiday scene, he remembered this one. He pulled it out, and then he thought, ‘They won’t want this–all the cars are from the ’50s.’ So he added two small cars from the ’60s on either end, coming and going.” Verisimilitude isn’t what it’s about, after all. Just at this moment, there’s a flurry of excitement in the waiting crowd as a cherry-red Mercury–a reasonable facsimile of the one in the painting–turns onto Main Street with Tony Carlotto at the wheel, in a fur hat and shorts. A small tree, its trunk wrapped in fabric to protect this great old car, is placed carefully on top. And the tableau is complete. The painting is finished. “It’s ‘home for the holidays,'” says Barbara Zanetti. “It brings back the small-town Christmas spirit that sometimes gets lost. It’s not an exact duplicate–we’re reenacting the feeling.” “I just love Stockbridge,” Norman Rockwell once said. “I mean, Stockbridge is the best of America, the best of New England.” And so for the next couple of hours we take in Rockwell’s town, strolling through the past, as it weaves through the present. All in all, it feels pretty good. And we have to agree with Meg Williamson: “The painting springs alive before your eyes.” The annual Stockbridge Main Street at Christmas celebration takes place December 4-6, 2015. stockbridgechamber.org/visit/stockbridge-main-street-at-christmas. More photos at: YankeeMagazine.com/Stockbridge-Christmas