Stockbridge — Back in 1773, Silas Pepoon opened a small tavern on the corner of Main Street. Pepoon’s tavern eventually became the Red Lion Inn, which has been operating at that same location for 250 years.
A fire destroyed the original building in August 1896, but it was rebuilt and opened back up for business in May 1897.
Since its opening in 1773 by Pepoon, its ownership has transferred and passed along over the years. The Plumb family, who purchased the inn in 1873, is responsible for the antique furniture and china that are still found throughout the inn.
The property was purchased in 1968 by Jack and Jane Fitzpatrick of Stockbridge. The couple moved their mail-order business, Country Curtains, into the building. Sarah Eustis, the granddaughter of Jack and Jane Fitzpatrick, is the current co-owner and operator of the inn, along with her brothers, Casey and Michael Fitzpatrick.

“It’s a great honor that we are still operating, and it is an accomplishment,” Eustis told The Berkshire Edge. “It’s great to honor things through the past and to think about the future. It’s also a great time to recognize how much hard work it takes to keep something like this continuing to evolve while staying modern and relevant. This is an important commitment we have made, along with keeping up with our guest’s expectations.”
There are 82 rooms in the inn itself, which was designated a member of Historic Hotels of America of the National Trust for Historic Preservation in 1989. “The reason why my grandparents purchased the Red Lion Inn was because they realized they needed a place to house their growing company,” Eustis said. “They also wanted to create an actual retail shop. But, right at the time the inn was coming up for sale, there was a potential for the building to be demolished and possibly turned into a gas station. My grandparents were preservation-minded people who saw an opportunity for their business.”

Over the years, the Red Lion Inn has hosted its share of world-famous customers. “One of the funny stories I have is that my grandfather, who became friends with Norman Rockwell, invited him to invest in the inn alongside him,” Eustis said. “But he said that he wasn’t interested. But Rockwell told my grandfather that he would be interested in helping him entertain his guests. Whenever my grandfather could, he would trot Norman out whenever he wanted as compensation for him not being able to invest in the inn.”
Eustis said that her grandparents recognized from the very beginning that the inn was not only worth saving for historic preservation’s sake but also because the Red Lion Inn is a hub for the community. “The inn is the heartbeat of Stockbridge, and my grandparents made it back into that,” Eustis said. “They hosted a lot of people here over the years. My grandparents were the ones who were committed to making the hotel vibrant and dynamic.”
Eustis first started working at her family’s inn as a housekeeper when she was 14. She said that she has fond memories of growing up at the Red Lion Inn. “I was always getting dressed up, and I always had my best manners,” she said. “You always had to have your best manners at the Red Lion Inn. My children have also spent their summers working here since they became of working age. It’s great because they learned how to relate to people and have gained skills that have served us well.”
Eustis said that she believes the Red Lion Inn will continue to operate for another 250 years. “I think that, no matter how much the times are changing and what is happening in the world, I think the quality of welcome and belonging is something that people feel strongly here at the inn,” she said. “This is something that has to be nurtured and maintained. We might move the furniture around in the inn, and we might have a new website all because we have to keep evolving as a business. The things that we have on our menu in our restaurant might change, or we might have new cocktails or change our uniforms. But in the end, the way we treat people is fundamental at the Red Lion Inn. It’s part of our core purpose to bring joy to people’s lives, especially when life feels more and more stressful.”
For more information about the Red Lion Inn, visit its website.