What it was like stepping into a Norman Rockwell painting this holiday season in Stockbridge (2025)

Travel

“It’s great. It’s wonderful. It’s Americana."

By Kristi Palma

December 12, 2024 | 11:20 AM

4 minutes to read

The bustling centuries-old Red Lion Inn was electric as Santa and Mrs. Claus entered the lobby in a flurry of red and white, waving and calling out “Merry Christmas.”

The iconic duo were about to climb onto an antique fire truck and travel down the stretch of Stockbridge’s Main Street made famous by American painter and illustrator Norman Rockwell in the 1967 painting “Stockbridge Main Street at Christmas (Home for Christmas).”

The Berkshires town closes the portion of the street to traffic and recreates the painting annually during its Stockbridge Main Street at Christmas event, which takes place the first weekend in December and draws about 3,000 people.

“It really is a beautiful way to kick off the holiday season,” said Barbara Zanetti, executive director of the Stockbridge Chamber of Commerce. “It brings you back to a simpler time where you just enjoy the community and your surroundings, especially in a world full technology.”

Its Main Street, recently featured on the “Today” show, hasn’t changed much since Rockwell lived and worked there during the last 25 years of his life (Rockwell died in 1978). Folks can still stroll by the library, the old town office, and the general store. Visitors can view the large-scale original painting at the Norman Rockwell Museum, two miles down the road.

The temperature hovered around 40 degrees for this year’s recreation, the 35th, and visitors filled the white wicker furniture along the 1773 Red Lion Inn’s sprawling front porch. Hundreds of folks gazed up from the sidewalk as the Berkshire Victorian Carolers, decked out in period clothing, sang “Jingle Bells,” “Joy to the World,” and other classic holiday songs from the porch.

Dozens of vintage cars from the ‘40s and ‘50s were parked in front of the buildings, just as Rockwell depicted them and then some.Tony Carlotto of Sheffield has been supplying the most prominent car in the painting for the past 26 years — a red 1955 Mercury parked before the inn with a Christmas tree on top.

“My mission is to make the whole world smile and I get a whole bunch of them in one day,” said Carlotto, dressed in festive holiday pants, as he climbed out of the car.

Indeed scores of visitors smiled for photos beside Carlotto’s car with the backdrop of the historic hotel. In the painting, the hotel is dark because it was a seasonal operation during Rockwell’s time, according to the Norman Rockwell Museum. There’s something else that’s not quite the same as in the painting: Rockwell added mountains to his scene.

Families and friends strolled the street in Santa hats, some with dogs on leashes dressed in Santa garb of their own. They stopped for photo ops at Norman Rockwell cutouts and they clapped for an entertainer named Roger the Jester. Santa and Mrs. Claus took photos with the day’s littlest visitors, while sheep filling in for Santa’s reindeer in a nearby pen — one wearing red antlers —delighted children waiting in line.

Other activities included horse-drawn wagon rides, children’s crafts, face painting, a Norman Rockwell Museum pop-up shop, and a station where folks could channel their inner Rockwell before his 1960 “Triple Self Portrait.”

Pat Bradley posed at the “Triple Self Portrait” station while his wife Ann Marie took photos. The couple drove from New York’s Long Island, attending the concerts and historic home tours throughout the weekend before the recreation on Sunday.

“It’s great. It’s wonderful. It’s Americana,” Bradley said.

Kevin Reuger of Sheffield, a faithful attendee of the event for the past decade, wore a Christmas suit dotted with snowflakes, Santa hats, and candy canes. What draws him back year after year?

“It pays respect to the old days,” Reuger said.

The twinkling Christmas tree in the window above the Stockbridge General Store matches the one in Rockwell’s painting. It marks Rockwell’s old residence.

Diners filled the cafes and restaurants on the small stretch of road and thirsty patrons lined up at the Red Lion Inn’s courtyard bar for cocktails, cider, and hot chocolate. A chili bar filled the space as well. Businesses were overflowing as folks bought “penny” candy, jams, and puzzles at the old-fashioned country store, and perused jewelry, crafts, and the work of local artists in nearby shops.

Inside St. Paul’s Episcopal Church, which is across the street from the Red Lion Inn and not featured in the painting, the Monument Mountain Regional High School students jazz ensemble played holiday songs to a packed crowd in the pews.

When asked if she felt like she was in a Norman Rockwell painting, Kayla Galasso from New York said, “Absolutely. Are you kidding me? That’s why we came here.”

Galasso’s children, Kinzley, 8, Mika, 3, and RJ, 2, climbed up into the seat of the antique fire truck parked on the street while her husband Ryan took their picture.

Claire Foley, 24, of Westfield, hung out with friends at the inn’s courtyard.

“I love the Normal Rockwell Museum,” Foley said. “So it’s fun to be transported back to a time when Christmas felt especially jolly.”