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Red Lion Inn operator Main Street Hospitality takes on resorts in Canada and Maine

Lions Den Photo 4 (copy)

Sarah Eustis, CEO of Main Street Hospitality, said the company has rebounded from the pandemic well and is looking to become involved in the right opportunities. "We are certainly in a growth period," she said.

STOCKBRIDGE — Main Street Hospitality Group has extended its portfolio of boutique hotels to nine by agreeing to manage two more lodging establishments, including one in Canada.

The Stockbridge-based operator of The Red Lion Inn and several other Berkshire lodging establishments will now manage the Chebeague Island Inn in Maine and Port Cunnington Lodge, which is located in Dwight, Ontario, roughly two hours north of Toronto. The Canadian project is Main Street’s first foray with a lodging establishment located outside of the United States.

Main Street CEO Sarah Eustis said both projects came about due to longstanding relationships that her company has with the owners of those properties. Port Cunnington Lodge has a Berkshire County connection through its owners, the Wadsworth family, which has ties to Williams College, The Porches Inn and the FreshGrass festival.

John “Jack” Wadsworth, a Williams College graduate and former member of the college’s board of trustees, and his wife, Susy, founded The Porches Inn with Eustis’ mother, Nancy Fitzpatrick. The Wadsworth’s son, Chris, who lives in San Francisco, founded the FreshGrass festival and Studio 9, a recording/performance space that is located inside The Porches. Main Street also manages The Porches.

“We were invited to provide management [of the Port Cunnington Inn],” Eustis said. “We have a 20-plus year relationship with the Wadsworth family. They’ve owned it for almost 30 years.”

Port Cunnington Lodge, located on the Lake of Bays in Ontario’s Muskoka region, which is near Lake Huron’s Georgian Bay, has been accepting guests for 120 years, according to a news release.

“When they indicated that they could use some help up in Canada, we jumped at the chance,” Eustis said. “It’s a nice fit in our portfolio.”

The Chebeague Island Inn is located in the Casco Bay region of Maine, a 25-minute ferry ride from Portland, the largest city in the state. The historic 20-room inn, built in 1880, is owned by the Prentice Group, whose owner, Casey Prentice, has worked with Main Street in the past.

Chebeague Island Inn photo

The Chebeague Island Inn in Maine is one of two boutique lodging establishments that Main Street Hospitality Group of Stockbridge has added to its management portfolio. 

Founded in 2014, Main Street Hospitality Group began expanding outside the Berkshires in 2018 when it agreed to manage the new Hammett’s Hotel in Newport, R.I. The company has since gone on to manage lodging establishments in Providence, R.I. and Hampton Bays, N.Y. The Chebeague Island Inn and Port Cunnington Lodge are strictly seasonal opeations — a first for Main Street, which until now has only been managing year-round properties.

Although the lodging business struggled during the COVID-19 pandemic, Eustis said Main Street has rebounded from the pandemic well and is looking to become involved in the right opportunities.

“We are certainly in a growth period for Main Street,” she said. “It (the company) is getting close to 10 years old and growth has been great. Now that we are solid and healthy post-COVID we are in a position to extend the portfolio, but only for the right relationships and the right reasons.

“We’ve had two great years evolutionally growing back from COVID in 2021 and 2022,” she said. “It indicated for us kind of a loyal following. The places we’re expanding to are places that people want to go to where they can have a relaxing experience in an authentic place where they can be close to nature. When the right project comes up with the right relationship, it clicks. We’re not daunted at all.”

In the Berkshires, Main Street Hospitality manages The Red Lion Inn and Maple Glen at the Red Lion Inn in Stockbridge, The Briaricliff Hotel in Great Barrington. The Porches, and an affiliated hotel, the Race Brook Lodge in Sheffield. The Fitzpatrick family owns the Red Lion Inn. A division of the family company owns The Briarcliff.

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