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Tradition, authenticity abound at this famous 18th century hotel in the Berkshires
It was established in 1773 and has hosted five U.S. presidents.
A centuries-old Berkshires hotel has hosted five U.S. presidents and inspired Norman Rockwell.
The 1773 Red Lion Inn, a charter member of Historic Hotels of America, is billed as one of America’s last great 18th century hotels. Travelers relax on period furniture amid centuries-old antiques and ride in an 1897 “birdcage” elevator.
“There is something special about the Red Lion Inn. It is unique. It is authentic. And it brings people joy, just being here,” said Tim Eustis, director of wine and catering sales, and a co-owner of the 125-room family-run inn.
Eustis is married to Sarah Eustis, who grew up working at her family’s hotel and would become a third-generation female innkeeper. She founded Main Street Hospitality Group in 2014, which manages the Red Lion Inn and eight other properties (with two more on the way).
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Rockwell, who once lived a few doors down from the storied inn, famously portrayed the building in his 1967 painting “Stockbridge Main Street (Home for Christmas).” Since, Main Street in Stockbridge has come to symbolize Christmas in America and the Red Lion Inn, a key player in the town’s annual reenactment of the painting, was recently featured on the “Today” show during its “Merriest Main Street” series. The inn was also named an ideal Christmas vacation destination by Conde Nast Traveler.
This December, a Christmas tree filled the inn’s lobby, decorated with pinecones, angels, and snowflakes. Figurines of carolers stood on the fireplace mantel as real carolers performed on the inn’s sprawling white porch decorated in greenery and sporting eight lit Christmas trees on its roof. The hotel hosts a month-long holiday celebration filled with live music, gingerbread house decorating, wreath-making workshops, and more.
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“The interesting thing about this place is that we have families that have been coming forever, like 20-plus years,” said Eustis. “They love coming back here and we love those traditions. That’s what makes the Red Lion Inn special.”
The longevity doesn’t stop at the guests: There are employees who have been working at the hotel for decades and the family’s apple pie à la mode has been served for generations.
Silas Pepoon established the small tavern in 1773, Eustis said, and it became a stop for stagecoaches traveling between Albany and Boston. Eustis called Stockbridge a “hotbed of revolutionary fervor,” and the inn’s website notes that “angry citizens from several towns gathered at Pepoon’s to pass resolutions protesting England’s repressive Acts of Intolerance.”
When Pepoon died, his widow took over the property, Eustis said. Several owners later, the inn was bought by Charles and Mert Plumb in 1873. Mert was a collector well known for her colonial antiques. Her teapot collection, china, and furniture were saved when the inn burned down in 1896 and they are all on display today.
The inn was quickly rebuilt and, for nearly a century, was owned by the Treadway family, who were descendants of the Plumbs. Private baths were added and a swimming pool was installed. The property was seasonal, which is why the windows are dark in Rockwell’s painting.
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In the 1960s the building was shuttered and in danger of being torn down before Jack and Jane Fitzpatrick bought it in 1968, said Eustis. The Fitzpatricks moved their successful mail-order company Country Curtains into the first floor, where they operated it for decades. Jack would go on to serve as a state senator and the couple had a big impact on the town of Stockbridge’s cultural offerings.
The Fitzpatricks, the grandparents of Sarah Eustis, expanded the property and made it a year-round Berkshires getaway that appealed to celebrities and even presidents.
Five U.S. presidents have stayed at the inn — Grover Cleveland, William McKinley, Theodore Roosevelt, Calvin Coolidge, and Franklin Roosevelt. Other famous guests have included writers Nathaniel Hawthorne, Henry Wadsworth Longfellow, Thornton Wilder, and William Cullen Bryant, actors John Wayne, Martin Short, and Steve Martin, and musicians Bob Dylan, Lyle Lovett, and Post Malone.
Over the years, the Fitzpatricks have added nearby guest houses ideal for larger groups. They have also added their own collections to those of Mert Plumb’s.
“The ceiling is chockfull of family relics,” said Eustis, pointing up at wooden toys, cookware, and more hanging from the beams of Widow Bingham’s Tavern, one of hotel’s four dining areas.
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In the nearby Main Dining Room, which has earned Wine Spectator‘s award of excellence, the vibe is more formal with white tablecloths and chandeliers. Other dining options at the inn include The Lion’s Den, a historic speakeasy with live music, and the seasonal Courtyard for patio dining.
Even as the inn honors its past, its leaders have an eye on the future.
Casey Fitzpatrick, the grandson of Jane and Jack and one of the owners, said in a video posted on the inn’s website, “I think the real challenge with the Red Lion Inn is to stay current and contemporary and be attractive to a contemporary and younger clientele while also really embracing the historic quality of it and knowing what doesn’t need to be changed and what does need to be changed.”
The Red Lion Inn hosts a traditional afternoon tea experience. And its second floor hallway doubles as an art gallery where British-based artist Charlotte Rose and actor/artist Billy Zane exhibited their work this year.
No matter the endeavor, the team follows the same philosophy, Eustis said.
“One of the things that the Fitzpatricks instilled upon us was something that Jane came up with long ago,” he said. “That is the philosophy of how we treat our guests.”
Eustis pointed to a sign above the employee entrance of the inn that reads: “Bringing pleasure to people is one of life’s greatest joys.”
The Red Lion Inn has boded well because of it, he said.
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“It has the quaintness and archetypical New England inn stuff about it that we find so charming,” Eustis said. “But you also marry that with the special sauce that Main Street Hospitality has launched from that quote, ‘Bringing pleasure to people is one of life’s greatest joys.’ So the combination of those two things is what makes the Red Lion Inn so special.”
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