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Red Lion Inn Celebrates 250 Years
By Brittany Polito, iBerkshires Staff
04:56PM / Saturday, September 23, 2023
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Nancy Fitzpatrick and Sarah Eustis with the lion of the Red Lion Inn at last week's 250th celebration.

Nancy Fitzpatrick's family has owned the inn since 1968. A third generation is now operating the inn and its related hospitality company.

Sarah Eustis, president and CEO of Main Street Hospitality, speaks to the gathering in the inn's patio.

Numerous notables have relaxed on the inn's famous porch.

The inn, not always called the Red Lion, has stood at the corner of Main and South streets in Stockbridge since 1773. Supposedly Ethan Allen stopped by along with a host of presidents, literary heavyweights, movie stars, singers and other celebrities. 

STOCKBRIDGE, Mass. — The community toasted 250 years of the Red Lion Inn and hoped for many more at a celebration last week. 

While the storied inn has a long history in Stockbridge, opening as a tavern just a few decades after the town was incorporated, it also has a long history in the Fitzpatrick family.

"My family is very, very proud for having stewarded the Red Lion Inn for over 55 years," Nancy Fitzpatrick said at the Sept. 14 gathering. "And we now are in the fourth generation of the family working here."

Her parents, the late Jack and Jane Fitzpatrick, purchased the Red Lion in 1968 and opened the seasonal resort year-round. Fitzpatrick, who retired a few years ago, found it incredibly rewarding to see so many former employees gathered around at last Thursday's celebration.

"I know that Red Lion has had an important role in their lives and they're all very important to us," she said.

Established in 1773 at the corner of Main and South Street, the inn has hosted many notable figures, including a half-dozen presidents, and is featured in Norman Rockwell's iconic 1967 painting "Stockbridge Main Street at Christmas." The inn is known for its classic New England charm, with people flocking to its porch to share a refreshment with friends and watch over the Main Street.

The third generation of Fitzpatricks have taken the reins, which includes Sarah Eustis and her brothers Casey and Michael Fitzpatrick.

"I think we all acknowledge that the Red Lion, not only is it an amazing place to gather and connect and make memories and mark the passing of time but it's a great place to learn how to work," Eustis said.

"And I think that is what I learned when I was 14. My sons are involved in the hotel and the education that comes from working with people, handling all the moving parts of a hospitality operation, have set us up well for for life in different ways."

Eustis is the CEO of Main Street Hospitality, which owns, operates and designs New England hotels and is headquartered in the Red Lion.

Over the years, she said, the values and genuine hospitality of the inn have stayed the same. The owners value family and community stewardship in their operations.  

"This place is more than a building. It's more than just bricks and mortar," Eustis said. "This place is living and breathing and people have all these memories and so whenever we change something, it's a big deal."

She pointed out that the Red Lion "runs on our own steam" without a foundation to support it, which sometimes requires incorporating new ways to optimize the campus.

One aspect that has received a facelift is the music program in the Lion's Den below the inn, which has been upgraded and requires a cover charge a couple of nights a week.

"The values and the genuine hospitality and the warmth that stayed the same," Eustis said. "The feeling of, we call it the brand of classic New England charm and the design of the place has essentially stayed the same."

She seconded her stepmother's statement that it is hard work to keep things the same.

"We want to honor the traditions and maintain the things that we love about the in and also keep moving forward," Eustis added. "We have to do both and that's the tricky part but it's also the fun part."

Simon Dewar joined the staff in the spring as general manager and as a part of the new leadership.

"I am on a daily basis humbled and honored to have been chosen to help continue this journey for another 250 years, we hope, along with working with such an incredible team," he said.

"And it's not common, believe it or not, within this industry but the team we have here, which is drawn from our community, are absolutely first class and I am extremely lucky."

Guests celebrated the anniversary in the courtyard with food, drinks, music and vendors.

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