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.

Tony Carlotto’s cherry-red vintage Mercury pulls onto Main Street with a small Christmas tree strapped to its roof—the centerpiece of the reenacted painting.

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 …READ MORE