The Inn at Longshore, an inspiration for ‘The Great Gatsby,’ to get multimillion-dollar upgrade

It was the kind of party that F. Scott Fitzgerald, author of “The Great Gatsby,” and wife Zelda would’ve enjoyed as The Inn at Longshore in Westport kicked off the summer season with a June 12 patio event in which 100 locals in sleek summer finery savored specialty cocktails, oysters, pizzas and passed hors d’oeuvres from the inn’s La Plage restaurant and the musical stylings of Joni & John. 

The literary reference is by no means idle. The inn – which the Greenwich Hospitality Group, owner of the Delamar Hotel Collection, leases from the town – will close at the end of the year for an $8 million renovation and expansion that is designed to preserve its character as a place that inspired Fitzgerald’s seminal 1925 novel. 

Said Greenwich Hospitality Group Founder and CEO Charles Mallory: “The building has undergone numerous alterations over the years. Our proposed changes aim to highlight its original architectural beauty. Our modifications are more appropriate than previous alterations.   

“I have consulted with Charles Scribner, whose family’s publishing house released ‘The Great Gatsby.’ He agrees that F. Scott Fitzgerald’s time in Westport, particularly relating to Longshore, likely inspired the novel. We plan to acknowledge this Gatsby heritage in our restoration plans.” 

The proposed refurbishment – spearheaded by Kenneth R. Nadler Consulting LLC in Mount Kisco – includes the addition of a small porte cochere, or covered entryway, to the white clapboard inn, which crowns the end of the winding, town-owned Longshore Golf Course; a new, waterfront entrance for the maritime-themed La Plage, helmed by Delamar corporate chef and partner Frederic Kieffer; the expansion of accommodations from 12 to 15 rooms, serviced by an elevator; a bridal suite, as the inn is a prime wedding venue; and upgrades to the roof, windows and mechanical system. A renovation of La Plage will be part of a second phase. Elements beloved by Westport residents – including the signature dome and red roof – will remain. 

With the remodeling of The Inn at Longshore, the presence of the Delamar Southport and the launch later this year of the Delamar Westport and its Dandelion restaurant of Mediterranean cuisine, the Greenwich Hospitality Group will have three complementary area venues to accommodate guests. (Farther afield, the Delamar Mystic, also opening later this year and including a La Plage restaurant, brings the total of Delamar hotels to five, including the Delamar West Hartford and the flagship Delamar Greenwich Harbor.) 

Guests, more like exiles, are very much what the Fitzgeralds were in the spring of 1920 when they arrived in Westport – then a blend of struggling, onion-blighted farmers-turned-Prohibition bootleggers, artists looking for a convenient, affordable retreat and new money – having been kicked out of the Commodore Hotel (now the Grand Hyatt New York, adjacent to Grand Central Terminal in Manhattan) for their incessant, alcohol-fueled partying. It was the dawn of Prohibition, but the Fitzgeralds, flush with cash from the sale of his first novel, “This Side of Paradise,” were content to let the good times roll, as was Connecticut, one of only two states, the other being Rhode Island, that never bothered to ratify Prohibition.  

 The couple rented the gray cottage at 244 Compo Beach Road across the street from the 175-acre Longshore estate of Frederick E. Lewis, the Tarrytown-born, multimillionaire adventurer, inventor, sportsman and philanthropist, whose mysteriousness did not prevent him from throwing elaborate parties and fundraisers featuring the likes of magician Harry Houdini, Russian ballerina Anna Pavlova, actresses Ina Claire and Marie Dressler and Connecticut Gov. Marcus Holcomb. It was catnip to Zelda, an international flapper and mermaid who couldn’t get enough of swimming. She in turn may have been a bit of catnip to Lewis, who kicked her out of one of his parties but continued to let her go skinny dipping off his private beach.  

The enigmatic millionaire, the festive, liquor-soaked estate, the cottage across the street, the dock across the water with its beckoning green light:  They’re all part of Fitzgerald’s “Gatsby,” the story of a poor soldier turned bootlegger who amasses and spends a fortune to impress a first love whose goodness is mostly a figment of his imagination. And they were all part of the Fitzgeralds’ sojourn in Westport. 

 Connecting the Westport dots first was writer Barbara Probst Solomon in a 1996 piece for The New Yorker. She would be joined 22 years later by Westport historian Richard Webb Jr., who grew up near the Fitzgerald cottage – still a private home, but now bearing a plaque to mark the Fitzgeralds’ tenure – to become author of “Boats Against the Current: The Honeymoon Summer of Scott and Zelda” (Prospecta Press, $40, 178 pages), and co-creator with Robert Steven Williams of the documentary “Gatsby in Connecticut: The Untold Story.” 

Some, like the late Fitzgerald scholar Matthew J. Bruccoli, have downplayed “Gatsby’s” Westport connection in favor of Long Island, where the novel is set and where it was written, in Great Neck. But novelists cull from a variety of sources to serve their narratives. 

“The good things and the first years…will stay with me forever…,” Fitzgerald wrote to his wife in 1934. By then, mental, physical, professional and financial challenges conspired to ensure that their Westport days were long past them. But thanks to The Inn, visitors  can stand on the shore in search of “The Great Gatsby’s” dock and green light, “like boats against the current, borne back ceaselessly to the past.”