Writing a New Chapter in Women-Led Hospitality

As the CEO of Main Street Hospitality Group, Sarah Eustis is both honoring a distinguished past and shaping a larger vision for the future.

The hospitality industry, like many other sectors, has historically been male-dominated at the leadership level. But for Sarah Eustis, the CEO of Main Street Hospitality Group, strong women have always been a force behind New England’s most iconic properties.

“I’ve had many titles throughout my career, but ‘third-generation female innkeeper’ is the one of which I’m most proud,” says Sarah. “Hospitality is in my blood.”

Learning the Ropes of a Purpose-Driven Trade
As a teenager, Sarah’s summers were spent at The Red Lion Inn in Stockbridge, MA, owned by her grandparents Jack and Jane Fitzpatrick. After the family purchased the inn in the late 1960s, Jane was the driving force behind a restoration of the historic inn, one of the best-known properties in the Berkshires. Jane’s daughter Nancy Fitzpatrick – Sarah’s stepmother – eventually took over the business and continued building on its long tradition of hospitality.

“I started as a housekeeper when I was just 14 and went on to hold almost every job they had to offer by the time I graduated college,” recalls Sarah, of her days working under her grandmother and mother’s tutelage. “Starting where I did gave me a deep appreciation for each of my next roles as I rose through the ranks, and that’s where I got the passion for all aspects of the business.”

This hard-won education would eventually make Sarah the most recent in a long line of women through the generations who shaped the Red Lion Inn through their grit, style, and entrepreneurial spirit. Anna Bingham, who founded the original inn as a general store and stagecoach stop with her husband Silas in 1773, after his death became the first woman business owner and licensed taverner in Berkshire County. Mert Plumb, who purchased the property with her husband Charles in 1873, transformed the inn with her passion for antiques, turning the “House of Plumb” into a veritable museum of early American furniture, china and art.

Over the years, the inn has hosted countless notables, including six American presidents and cultural tastemakers and stars like Gloria Steinem and Paul Newman. The property was even immortalized in a famous 1967 painting by Norman Rockwell, who also lived in Stockbridge. From the grand custom of formal dining to The Red Lion Inn’s lovingly curated collection of treasures, the experience of growing up in the midst of the inn’s gracious pageantry made a deep impression on young Sarah.

“I thought that this was like the most magical kingdom,” she remembers. “It was ingrained in me at a young age that hospitality is a noble, important trade that makes for a rewarding career.”

But her journey towards a role in hospitality leadership was a winding road. After college, Sarah embarked on a two-decade career in fashion, working with some of the most inspiring leaders and brand developers in the business. Across the companies she worked for – from Ralph Lauren and Gap Inc. to Etam and Limited Brand – Sarah saw that as family-owned businesses, they all shared the sense of deep-rooted purpose she felt in her own family’s stewardship of The Red Lion Inn.

“The founders of the lines were always present to remind us why the business started, which supplied a special connection to what we were doing,” she reflects.

So, when Sarah wanted to return to the States after a stint in Paris, she decided to see what new value she could bring to the hospitality industry by building on the legacy of her own family’s business.

“The essentials I learned in fashion seemed to translate well to hospitality,” says Sarah. “You design a thoughtful product, price it fairly, provide a great environment for your guests to experience it, tell a consistent story, and always smile at people.”

So, in 2013, she set out to make her mark by joining her stepmother Nancy in founding the Main Street Hospitality Group. Beginning with The Red Lion Inn as the cornerstone, this family-owned and female-led business has expanded to become a leader in the independent hospitality landscape focused on preserving properties with rich histories and strong ties to their local communities.

Growing the Legacy of Women-Led Independent Hospitality
Nearly a decade later, Main Street Hospitality has built on its philosophy of “building what matters, preserving what lasts,” to grow a portfolio of independent hospitality properties in the Northeast.

With expertise in the preservation and elevation of historic properties, it’s no surprise that Main Street’s family of hotels includes such gems as Canoe Place Inn & Cottages, a beautifully restored landmark in the Hamptons that is the site of the country’s oldest inn, and Chebeague Island Inn, a gracious 19th-century retreat overlooking Casco Bay on the coast of Maine.

Other properties are new builds or reimaginings, offering chic luxury for discerning travelers. Destinations like The Beatrice, a luxury hotel in downtown Providence, and Hammetts Hotel, a boutique hotel on the waterfront of Newport, invite travelers to take a break from the daily grind and savor their surroundings.

The Porches Inn at MASS MoCA, a row of restored Victorian row houses lovingly restored with unique common spaces, embodies the company’s commitment to working at the corner of culture and hospitality. Steps away from one of the country’s largest collections of contemporary art, Porches has hosted artists in residency as well as notable Americana roots artists drawn to its onsite recording studio in the Northern Berkshires.

The company’s roots in the Berkshires have grown as they expand the options for travelers looking to explore the region’s natural and cultural treasures. Hotel Downstreet, on Main Street in the historic town of North Adams, just opened this year, while The Briarcliff Motel in Great Barrington preserves a piece of 20th century history as a transformed roadside inn.

Nor has Main Street been shy about planting new flags. It recently welcomed its first international property, Port Cunnington Lodge, a historic resort on the Lake of Bays in Muskoka that offers travelers a time-honored retreat from the hustle and bustle. And it oversees the operations of Scales and Shells, a Newport dining institution since 1987.

Even as Main Street expands its horizons, Sarah notes that the common thread that ties together all her decisions traces back to her family’s dedication to the art of hospitality.

“I often think about how my mother and grandmother focused on bringing pleasure to people through attention to detail and preserving traditions that are meaningful to guests, even if it is simply the position of a rocking chair in front of the fireplace,” she says. “I still hear them both in my ear when I am making decisions about everything from new projects to updating wallpaper, to advanced new technology we might deploy.”

And there is plenty to do, with new projects on the radar as well as plans to celebrate the 250th anniversary of The Red Lion Inn. Several years ago, Sarah led the reopening of The Lion’s Den, a circus-themed bar created by the inn’s owners in 1937 shortly after the end of Prohibition. With a regular lineup of live music, biannual art exhibits and more upgrades on the horizon under The Red Lion Inn’s master plan, there’s an energy that keeps this historic property alive and blooming.

“To steward this magical place that means so much to so many is an honor,” says Sarah. “It is really an incredible legacy.”