The Real Gatsby

East Egg, West Egg and its connection to Westport

Written by MaryEllen Fillo

Imagine it through the eyes of famed author F. Scott Fitzgerald. A mysterious millionaire, a luxurious estate, outrageous parties with couture-outfitted celebrities and special guests, hot jazz and dancing, free-flowing liquor and sumptuous buffets. It is the quintessential 1920s party setting that set the stage for his masterpiece, “The Great Gatsby.” The place? It might be closer than you think.

The Inn at Longshore in Westport, a Delamar property, is considered one of the premiere wedding and special event venues in Fairfield County. And along with its elegance and coveted reputation comes an intriguing back story, strong suggestions that the site may have been part of the inspiration for F. Scott Fitzgerald’s classic novel.

As academics debate exactly what really inspired the Fitzgerald’s famed story of the fictional millionaire, Jay Gatsby, and his love affair with another main character, Daisy Buchanan, The Inn at Longshore has emerged as one of the Connecticut shoreline sites that may have contributed to the author’s imaginary tale written nearly 100 years ago.

“For so many years, it was believed that the inspiration, storyline and elements of the novel for ‘The Great Gatsby’ stemmed from his time on Long Island,” said Robert Steven Williams, who with historian Richard “Deej” Webb, produced the documentary “Gatsby in Connecticut: The Untold Story.” The documentary, currently being screened at several universities and theaters around the state, contends that Fitzgerald’s extended Connecticut stay with his wife Zelda in 1920, was tapped as part of the story line in the American classic. Extending the theory of Barbara Probst Solomon, who first wrote the Westport connection in a New Yorker magazine article , Williams, a filmmaker, songwriter, novelist and Westport resident, and Webb, a former history professor and author of “Boats Against The Current: The Honeymoon Summer of Scott and Zelda,” offers further evidence that some of the inspiration for Gatsby’s estate and Nick Carraway’s (another main character in the book) guest house (the place the Fitzgerald’s honeymooned), was not solely a Long Island setting, but instead The Inn and its nearby, privately-owned Compo Road residence.

The Inn was the onetime estate of mysterious, millionaire Frederick E. Lewis. The estate was hopping according to Williams and Webb’s research, a party place fueled by a cultural shift that included prohibition, a surging economy and excessive indulgence. The Fitzgeralds lived in Westport for several months. The couple, and especially the very spirited Zelda, were regular guests at the over-the-top parties and places that uncannily paralleled those that were featured in the novel.

“We found articles of fabulous parties there and it is interesting that little is known about Lewis, “ said Williams noting that it seemed as if Lewis had been “scrubbed” from existence as one of Westport’s elite. “We dug down and found his grandson and obtained tons of photographs and read tons of newspaper clipping and got a strong sense of who the man was,” Williams continued. “There is absolutely the essence of Gatsby.” The ties between the Westport places and geography in a few of Fitzgerald’s books as well as one of his wife’s, are undeniable and offering some interesting opportunities to residents and visitors.

The Westport Museum of History and Culture are offering “Destination Westport: In Gatsby’s Shoes” from time to time. The 90-minute walking tours, according to Nicole Carpenter, its director of programs and collections, combine the history of a then bucolic Westport with the story and places Gatsby visited and lived in the town that influenced Fitzgerald’s novel..

Williams said he was surprised at how many Westport residents are not familiar with the Fitzgerald history in town, including actor Sam Waterston, who played Nick in the 1974 movie version of the book.

“He was graciously giving us an hour to be part of the documentary,” said Williams. “He stayed the whole day because he found the connection to Westport so fascinating.”

Christine Hussey, director of sales and marketing at The Inn, said there are guests that do ask about the Fitzgerald and Great Gatsby connection with The Inn, and that Webb’s book has been available to guests at The Inn that includes a ballroom, the restaurant and 12 guest rooms. The Inn is slated for an $8 million renovation beginning in 2025.

For information on the documentary screenings go to gatsbyinct.com

For information on the Gatsby walks go to westporthistory.org

For information on The Inn go to innatlongshore.com