The Red Lion Inn in Stockbridge, MA | A Historic New England Inn at Christmas

While it’s true that the Berkshires town of Stockbridge, Massachusetts, is a year-round gem, combining natural beauty with small-town charm and top-notch attractions that keep visitors coming back year after year, perhaps at no time is it more charming than at Christmas. For one special weekend each December (November 30 – December 2 in 2018), two of Stockbridge’s greatest treasures, the historic Red Lion Inn and former resident Norman Rockwell (both in spirit and thanks to the terrific Normal Rockwell Museum) come together for Stockbridge Main Street at Christmas. We were so charmed by the town-wide celebration that it became our cover story in the November/December 2014 issue, so that same year, I made the trip to Stockbridge with fellow Yankee Kate Hathaway Weeks to be there for the event.

The Red Lion Inn, which has been in operation since the late 18th century, is large and sprawling today — the natural product of centuries of growth — with a wide and welcoming front porch. Inn history says that it was first founded as a market around 1773, but quickly grew to a tavern and inn under the crest of a red lion waving a green tail (the red lion is thought to symbolize the British crown, and the green tail sympathy for American independence).

Despite a fire in 1896 and a tense era during the mid-20th century when the inn was almost leveled and replaced with a gas station, it has (fortunately) survived. In November 1968, Stockbridge residents Jack and Jane Fitzpatrick, the founders of Country Curtains (now part of the Vermont Country Store) rescued the inn with plans to use the building for their business, but were so charmed by its history that they decided to keep running things as they were. Extensive updates and renovations were carried out, with an emphasis on historic preservation and making use of the inn’s trove of antiques, and in May of 1969, The Red Lion Inn was re-opened as a year-round operation. Still a family business, their daughter Nancy owns and operates the inn today, which has grown to include several guest houses within walking distance of the main building. While I’d visited Stockbridge before (see Visit to Stockbridge and the Norman Rockwell Museum), it was only for a quick day trip, so this time around I was really looking forward to doing a bit more exploring. As you can see, even in winter with snow on the ground, the inn’s porch rockers find willing bodies to sit and enjoy the view.

Inside, the impossibly cozy lobby is enough to make many swoon (if you’re into the charming parlor thing, which I am). At no time during my 2-day visit were its scattered sofas and chairs empty, and I got the impression that some folks, having settled in with their coffee and newspaper, had no intention of giving up their prized seat anytime soon — not that I blamed them. This is a lobby that functions more like your favorite grandmother’s living room, complete with antiques (the teapots over the mantel are just a few of the inn’s 200+ collection) and overflowing dish of gum drops.

There’s also an ornate 1897 birdcage elevator tucked into one corner of the lobby that’s worth checking out, but you’ll need a staff member if you want to take a ride!

The inn has 4 dining spaces — the seasonal outdoor courtyard, Lion’s Den pub on the lower level, elegant main dining room, and cozy Widow Bingham’s Tavern, all serving tasty meals using fresh, local ingredients. Especially recommended are the Roasted Native Turkey with Cornbread Stuffing & Cranberry Sauce, Lila’s Mountain Lamb Shepherd’s Pie , and Warm Brown Sugar Cake.

Just off the tavern you’ll also find a few interesting things to see. First, the inn’s two “telephone rooms”…

And on the wall, a folk art collection of vintage pencils that were a lot of fun to look at, purchased by the inn’s owner at an auction.

The maze of rooms at the Red Lion Inn is part of what makes strolling the building so much fun. You never know what’s going to be around the corner. Upstairs, crooked hallways are comfortably cluttered with artwork, antiques, and furniture. If you hate the feeling of modern cookie cutter hotels, you’ll love both wandering and staying at the Red Lion Inn. Not only are the rooms well appointed and comfortably updated, but you can be sure that what’s outside your room (and likely even what’s in it) is one of a kind. Also, with so many years in operation, it’s no surprise that The Red Lion Inn has had its share of famous guests. Five presidents have been guests at the inn (Cleveland, McKinley, Theodore Roosevelt, Coolidge, Franklin Roosevelt), and celebrities like Oprah Winfrey, John Wayne, Bob Dylan, Tony Bennett, and Billy Joel have also checked in, plus a host of writers like Nathaniel Hawthorne, Henry Wadsworth Longfellow, Thornton Wilder, and William Cullen Bryant.

After a delicious dinner in the main dining room, which included Indian Pudding for dessert for me, we got a good night’s sleep in anticipation of Sunday’s main event. But not before a quick field trip on Sunday morning! Stephanie Gravalese, the inn’s friendly and knowledgeable marketing and communications manager, took us to one of her favorite spots in nearby West Stockbridge for a breakfast worth singing about. Owned and operated by Flavio Lichtenthal and Lisa Landry, the Six Depot Roastery and Cafe (housed in the town’s old train station) serves as a small-batch coffee roastery, café, art gallery, and event space. Boasting quality coffees and teas (expertly prepared) plus a tempting menu of sweet treats, sandwiches, and salads in a bright and sunny space…well, we wanted to try everything.

After enjoying a delicious spread of lattes, breakfast sandwiches, and pastries, we picked up a few gourmet food items to take home, admired the artwork for sale in the cafe’s adjoining event space, and then headed back to Main Street for the weekend’s big event, caffeinated and ready. If you’ve read the cover story in the November/December 2014 issue (Stockbridge Main Street at Christmas | Home for the Holidays), then you know that, each December, the town of Stockbridge and a bevy of visiting tourists “step inside a Norman Rockwell painting come to life” as the town reenacts Rockwell’s iconic Stockbridge Main Street at Christmas painting. This includes blocking off the section of Main Street depicted in the painting, with vintage automobiles parked in the right spots. The day’s activities also include horse drawn rides, a visit from Santa, caroling on the porch of the inn, and a whole lot more. Armed with tasty Dancing Deer gingerbread cookies and copies of the Gingerbread Recipe with a History story from the issue, Kate and I set up on Main Street to chat with readers and enjoy the fun.

It was a perfect day for winter celebrating — meaning sunny and dry, with just enough of a nip in the air to keep folks lined up at the inn’s concession table for chowder and hot chocolate (special thanks to Stockbridge Police Chief Robert M. Eaton for personally delivering two much appreciated hot chocolates to the Yankee table!), and slowly, the recreation began to take shape.

The cars were a lot of fun to admire, but there were other festive participants, too.

Meanwhile, back at the inn… A festive sleigh with the Yankee cover behind it serves as the perfect setting for a Christmas photo.

And inside, the inn’s main rooms hummed with crowds warming up from the cold by enjoying carols, browsing the gift shop, and tucking into lunch. Each holiday season, the inn uses 31 fresh Christmas trees throughout the property, 125 fabric wreaths made from recycled wood (a lovely addition to guest room doors), 30 kissing balls, 45 poinsettias, 54 window boxes, and around 800 feet of garland! That’s a lot of cheer!

Towards the back of the dining room you won’t want to miss the candy Red Lion Inn replica, decorated by Jessica Maruco (pastry chef at The Williams Inn in Williamstown, MA) and built by Edouard Vavel, a master craftsman who also teaches woodworking at the nearby Austen Riggs Center.

Time to say goodbye for now, Red Lion Inn. Thanks for a wonderful and festive visit!

Have you ever visited Stockbridge or stayed at a historic New England inn like The Red Lion Inn? Want to attend this year’s Stockbridge Main Street at Christmas? It takes place from November 30 – December 2, 2018! This post was first published in 2014 and has been updated.