Roger Sherman’s inn-spired reimagining

What’s next for the Roger Sherman Inn? If we learned anything from 2020, it is that the future is impossible to forecast. But smart money will say that the celebrated establishment will change with the times and still be in the spotlight for years to come.

It is not uncommon for a hospitality destination to reinvent itself in response to changing times, trends and tastes. But few establishments have ever experienced the dramatic evolutions of New Canaan’s Roger Sherman Inn. 

The landmark dates from the mid- or late-18th century — historical sources offer differing dates regarding when construction actually took place on the 22-acre lot at Haynes Ridge Road, the original name of the thoroughfare that is today’s Oenoke Ridge Road. It was the home of the Rev. Justus Mitchell, minister of the Congregational Church, and his wife, Martha Sherman, the niece of the Continental Congress delegate Roger Sherman. 

In addition to providing for the parish’s spiritual needs, Mitchell was also responsible for establishing a private school and a library. However, Mitchell was not a modern-style progressive — the school was designed to prepare young men for an education at Yale University while the library’s membership was restricted to what the late 18th century described as “gentlemen contributors.”

Historic turnarounds

The Rev. William Bonney, who succeeded Mitchell as the pastor for the Congregational Church, purchased the house in 1809. It changed hands four times during the first part of the 19th century until New York financier William E. Bond acquired it, in 1868 and made expansive renovations befitting the extravagant aesthetics that defined the Gilded Age tycoons. 

The property would change hands again in 1925 when J. Herbert and Louise Stevenson Tebbetts acquired the space, adding more rooms and a wraparound porch. But rather than maintaining a private residence, the Tebbetts opened the building with a twin purpose — as a 17-room lodging spot known as the Holmewood Inn and an educational facility called the Holmewood Junior School.

The Tebbetts’ school closed after three years, but the inn remained operational and quickly became a local favorite for its emphasis on fine dining. It was purchased by hotelier John D. Shea in 1946 and was sold in 1960 to a New Jersey country club manager named Roger Sherman Ross, a direct descendant of the colonial patriot, for whom it was renamed.

Enter the Jaffres

Real estate investors Nesreen and Joseph Jaffre, who previously owned Le Château in South Salem, bought the Roger Sherman Inn in 2008 for $3.4 million with the goal of continuing the establishment’s culinary reputation. The Jaffres brought in Christophe Cadou as the executive chef and the inn’s cred spread beyond New Canaan.

In a November 2008 review, New York Times restaurant critic Patricia Brooks lavishly praised Cadou’s creations, proclaiming, “It’s been a long time since I have seen a menu so appealing that I’ve wanted to order every single dish … Not only was almost every dish expertly prepared and very fresh-tasting, but the plate presentations were uniformly lovely and appetite-inspiring, without looking ‘played with.’”

Brooks gave particular attention to Cadou’s roasted Colorado rack of lamb with thyme-rosemary jus, noting how she has not enjoyed “such tender, flavorful lamb in a very long while.” She also gave kudos to pastry chef Chelsea Spielmann, noting that her dessert creations “were as perfect as the rest of the meal.”

Alas, the delicious meals were not enough to shield the inn from the tumult of the Great Recession. With a shrinking revenue stream and what appeared to be limited opportunities for a turnaround — as well as the defection of Cadou from the kitchen in 2013 — the Jaffres listed the inn for sale in August 2014 at $6 million. After remaining on the market for more than two years, a sale was announced — not to a hotelier, but to Rowayton real estate developer Andy Glazer, who offered to buy the property and transform it into a development with eight single-family homes. 

‘Hosting’ Prince Harry

The Jaffres initially announced the closure of the inn in January 2017 pending the planning and zoning commission’s approval of the sale. But local opposition to Glazer’s plans was well-organized and highly vocal and the commission rejected Glazer’s initial proposal and two updated ones. 

“Although it is a staple in New Canaan, the community needs to know that it requires their support,” said Nes Jaffre in a September 2017 interview with the Fairfield County Business Journal. “It requires the public’s help in keeping it open. This is not a building that is supported by government grants or public subsidies. You can’t go there once a year and claim that you are supporting it.”

The Jaffres managed to chart a new course by recruiting François Kwaku-Dongo, the Ivory Coast-born chef who gained international prominence in 1991 as executive chef at Wolfgang Puck’s Spago in West Hollywood. Kwaku-Dongo’s presence at the inn created a media frenzy and brought renewed attention to the establishment. Clever promotions, including viewing parties for the Kentucky Derby and Prince Harry’s wedding to Meghan Markle, brought in more patrons, and all seemed to be full-systems-go when 2020 rolled around.

Of course, 2020 was not the year anyone expected and the inn reinvented itself yet again as the Covid-19 pandemic temporarily forced its closure. Following the lead of other eateries, the inn launched its “Roger on the Go” menu for curbside pickup, offering some rather eclectic takeout choices, including Escargots à la Bourguignonne, Beef Stroganoff and Lamb Osco Buco. Outdoor dining resumed in May along with live music by socially distanced local performers. July, brought more good news with Cadou’s return after a seven-year absence.

“We can’t be more thrilled,” Nes Jaffre exclaimed on Facebook. “I know you will be too. Whew! Relief!!!”

What’s next for the Roger Sherman Inn? If we learned anything from 2020, it is that the future is impossible to forecast. But smart money will say that the celebrated establishment will change with the times and still be in the spotlight for years to come.

Roger Sherman Inn is at 195 Oenoke Ridge Road. For more, call 203-966-4541 or visit

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