May 14th marks Gatsby Day for Westport. The holiday was proclaimed in 2019 by First Selectman Jim Marpe, alongside local author and Westporter Deej Webb, film producer and Westporter Robert Steven Williams, and Westport Museum Executive Director Ramin Ganeshram.

The day celebrates the famous story and its author, short-time Westporter F. Scott Fitzgerald. Fitzgerald and his wife Zelda rented a home on Compo Road South, just prior to Longshore Club Park, in the summer of 1920. It’s rumored that the famous story, The Great Gatsby, had more influence from Westport than originally thought.

The Honeymoon Summer of Scott and Zelda Fitzgerald

Richard “Deej” Webb, Author

The Great Gatsby has long been synonymous with Long Island, but what if Fitzgerald’s true inspiration came from here in Connecticut? 

Scholars have dismissed the influence of the Fitzgeralds’ idyllic period in Connecticut, but Westport holds answers to questions that can’t be answered by only studying Long Island. This fascinating realization was at the heart of the documentary written by Richard “Deej” Webb and Robert Steven Williams in their film that combines real detective work with a paean to the Jazz Age: GATSBY IN CONNECTICUT: The Untold Story.  Webb also recounts the work it took to create the film in the companion book Boats Against the Current: The Honeymoon Summer of Scott and Zelda.

In the June 4, 1920 edition of the Westporter-Herald there was a small item about a new resident: “F. Scott Fitzgerald, a writer, has leased the Wakeman Cottage near Compo Beach.”  The modest gray cottage in Westport, Connecticut was the honeymoon home of Scott and Zelda Fitzgerald for five months in the summer of 1920. It had such a profound impact on both of them that it appears in more of their collective works than any other place where they ever lived. 

It was, for Scott and Zelda, their honeymoon. Having just gotten married and after being kicked out of some of New York city's finest hotels, they were, for the first time, in their very own place, albeit for only five months. It was a time that Scott Fitzgerald called "the happiest year since I was eighteen."He had, after all, just achieved success with his first novel, This Side of Paradise, and was suddenly awash with money.

The Fitzgeralds lived a wild life of drinking, driving and endless partying while living in suburban Connecticut. As it happens, living near the beach, they were neighbors to a larger-than-life reclusive multi-millionaire, F.E. Lewis. 

GATSBY IN CONNECTICUT and Boats Against the Current tells the real story behind the famous novel and its tragic hero, debunking the long-held belief that the book was solely inspired by the Fitzgerald s time in Great Neck, across the Sound in Long Island, and lays out enough information about the fascinating Mr. Lewis that it is difficult not to believe that he is the true inspiration for one of the most captivating and iconic characters in American literature, the great Gatsby himself.