…and that’s because it is a Norman Rockwell painting!
Stockbridge, Massachusetts is many things, hometown of celebrated illustrator Norman Rockwell, location of the historic 250-year-old Red Lion Inn, and one of the quaintest holiday towns you’ll ever visit!
Country Living recently ranked Stockbridge at the number 4 spot on its list of “The 30 Most Magical Christmas Towns in the U.S.!”
Stockbridge might look just like a Norman Rockwell painting—and that’s because it is! Each year, the town re-creates the 1967 Rockwell painting, “Stockbridge Main Street at Christmas (Home for Christmas)” during their annual festival. Old-fashioned cars line the main street to re-create the painting, and the public can tour historic homes decorated for the holidays.
While it is a small town, there is so much storybook holiday fun to be had in this quaint town. The population of 29,000, is incredibly tight-knit and welcoming, with strangers wishing you a happy holiday season everywhere you go. It’s something straight out of a movie.
Visting Stockbridge, Massachusetts in the holidays
Winter is one of the best times to visit Stockbridge, starting in December especially! Main Street is dripping in holiday lights and sparkling snowflakes fall from the sky above. You can do everything from ride a horse drawn carriage to visiting one of the top light shows in the state in this adorable town. January through March bring great outdoor winter recreation like skiing, sledding, and more.
Where to stay
To be at the heart of it all, make sure to book your stay at The Red Lion Inn. Operating as a tavern initially, the inn came to fruition in 1897. You can board a vintage 126-year-old antique elevator, make friends with the hotels two cats-in-residence, or swim in the outdoor heated pool year-round! The pet-friendly hotel also has incredible farm-to-table dining and two local gift shops on-site!
This historic inn is one of the Historic Hotels of America of the National Trust for Historic Preservation, and one of the top 25 hotels in the Northeast according to Condé Nast Traveler 2023 Readers’ Choice Awards!
What to do
Staying at The Red Lion Inn is like living in a Norman Rockwell illustration! Because you are!
The historic inn is part of Rockwell’s 1967 illustration, Stockbridge Main Street at Christmas, “Home for Christmas.” The town is also home to the Norman Rockwell Museum which is a must-visit! The museum houses all 323 Norman Rockwell covers for The Saturday Evening Post.
You can’t go to Stockbridge without visiting one of the state’s most popular light shows. Naumkeag Winterlights is a must, with one million lights in every color of the rainbow! It takes place at one of the Berkshires’ 70 Gilded Age mansions built as “summer cottages.” You can board the complimentary holiday shuttle from outside The Red Lion Inn directly to the holiday lights display.