Everyone assumes The Great Gatsby is a Long Island book. You think of Leo DiCaprio in a pink suit, the green light blinking across the water from East Egg to West Egg, and the sprawling mansions of the North Shore. But honestly? The real Gatsby in Connecticut: the untold story starts in a gritty, booze-soaked summer in Westport, long before F. Scott Fitzgerald ever set foot in Great Neck.
It was 1920. Scott and Zelda were the "it" couple of the century, fresh off the success of This Side of Paradise. They were young, reckless, and looking for a place to hide from the chaos of New York City. They ended up at a gray shingle house called "Wakeman Cottage" on Compo Road South. It wasn't some grand estate. It was a rental. But right next door was a massive, mysterious property owned by a multi-millionaire named F.E. Lewis.
That’s where things get interesting.
Why Westport is the Secret Heart of the Novel
Barbara Probst Solomon, a late, legendary essayist for The New Yorker, basically blew the lid off the Long Island myth years ago. She grew up in Westport and realized that the geography of West Egg doesn't actually fit Great Neck. It fits Westport. When you look at the proximity of the "valley of ashes" and the way the water cuts into the coastline, the Connecticut landscape starts to look a lot more like the world of Jay Gatsby than anything in Nassau County.
The Lewis estate was the spark. Frederick E. Lewis was an eccentric wealthy guy who owned a huge chunk of land where Longshore Club Park sits today. He had a private yacht, a private landing strip, and he threw parties that were loud enough to keep the neighbors—including the Fitzgeralds—awake all night. Scott was watching. He was taking notes on the way the light hit the water and the way the "nouveau riche" behaved when they thought nobody was looking.
Westport wasn't just a quiet suburb back then. It was a wild frontier for the wealthy. It had that specific blend of old-world Connecticut money and the fast, dirty cash of the Prohibition era. You’ve got to remember that Fitzgerald was obsessed with class. In Connecticut, he saw the collision of these two worlds up close. The "untold story" isn't just about a change of scenery; it's about where the psychological blueprint for the most famous American novel was actually drawn.
The Mystery of F.E. Lewis and the Real Jay Gatsby
Who was the man behind the curtain? While Max Gerlach is often cited as the primary inspiration for Gatsby’s "Old Sport" persona, F.E. Lewis provided the physical scale. Lewis was a man of immense, almost incomprehensible wealth. He didn't just have a house; he had an ecosystem.
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His estate had its own power plant. It had a massive water tower. There were barracks for his private security. It was a fortress of excess. To a young, struggling writer like Fitzgerald, living in a modest cottage nearby, the Lewis estate must have looked like a kingdom.
- The Yacht: Lewis had a 150-foot steam yacht called the Stranger. In the book, Gatsby’s life changes when he sees Dan Cody’s yacht.
- The Parties: Local legends in Westport still talk about the sheer volume of the Lewis bashes. We aren't talking about tea and crumpets. We're talking about industrial-scale entertainment.
- The Isolation: Much like Gatsby, Lewis was a bit of an enigma to his neighbors. He was there, but he wasn't there.
If you walk through Longshore Club Park today, you can still feel the ghost of that era. The rolling greens and the view of the Sound haven't changed that much. You can almost see the yellow car tearing down the narrow roads.
The Valley of Ashes: A Connecticut Connection?
In the book, the Valley of Ashes is a desolate stretch of land between West Egg and New York. Most scholars point to the Corona Ash Dumps in Queens. That makes sense for the Long Island version of the story. But if we're looking at Gatsby in Connecticut: the untold story, we have to look at the commute Scott took from Westport to the city.
Back in 1920, the trip from Westport to Manhattan was a slog. You passed through industrial hubs like Bridgeport and Norwalk. These were gritty, smoke-belching towns full of factories and laborers. The contrast between the pristine beauty of the Westport shoreline and the industrial decay of the nearby cities was jarring. Fitzgerald was a master of contrast. He saw the "ash-grey men" who moved "dimly and already crumbling through the powdery air." That imagery wasn't just pulled from a map of Queens; it was pulled from the reality of 1920s industrial New England.
Zelda, the "First American Flapper," in Westport
We can't talk about the Connecticut summer without talking about Zelda. She was the fire to Scott's ice. In Westport, she was notorious. There are stories of her dancing on tables at the local inns and swimming in Long Beach at midnight. She was the living embodiment of Daisy Buchanan—or at least, the wilder parts of her.
The Fitzgeralds were eventually kicked out of their Westport rental. Not because they couldn't pay the rent, but because they were too loud, too drunk, and too much for the quiet Connecticut neighbors. They were "careless people," as Nick Carraway would eventually describe Tom and Daisy. They smashed up things and creatures and then retreated back into their money or their vast carelessness.
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Westport was their playground, but it was also the place where their marriage began to show its first real cracks. The tension of that summer, the heat, the booze, and the proximity to extreme wealth created a pressure cooker. When Scott sat down to write the novel a few years later in France, the memories of Connecticut were the ink in his pen.
Why the Long Island Myth Won
So, if Connecticut is the real birthplace of Gatsby, why does everyone think it's Long Island?
Marketing, mostly. And the fact that the Fitzgeralds did move to Great Neck later. By the time the novel was published in 1925, they had spent significant time on Long Island, and it was a more recognizable symbol of high society for the New York publishing world. Long Island was the "Gold Coast." It had a better ring to it.
But the emotional core—the feeling of being an outsider looking in at a massive estate—that happened in Westport.
The Evidence in the Text
If you look closely at the text of The Great Gatsby, there are weird little slips. Nick Carraway mentions that he's from the Midwest and comes East to learn the bond business. He talks about the "wet barns" and the "red gas pumps" of the commute. While these fit Long Island, they are almost carbon copies of the scenery along the Post Road in Connecticut during the early twenties.
Also, consider the distance. West Egg and East Egg are described as being separated by a "courtesy bay." In Westport, the Saugatuck River and the various inlets of the Sound create these small, intimate pockets of land where you can see your neighbor’s dock but can’t easily get there. It’s a physical manifestation of the social barriers Fitzgerald was obsessed with.
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How to Experience the "Untold Story" Today
If you're a Gatsby fan, you don't go to Great Neck. You go to Westport.
Start at Longshore Club Park. This was the heart of the F.E. Lewis estate. Walk out to the point where the land meets the water. Look across towards the other side of the inlet. That’s your green light. The original mansion is gone, replaced by the inn and the golf course, but the layout is still there. You can feel the scale of the ambition that Lewis had—and that Gatsby inherited in fiction.
Then, drive down Compo Road South. Find the spot where Wakeman Cottage stood. It’s a private residence now, so don't be weird and trespass, but just driving that road gives you a sense of the scale. It's a narrow, winding road that feels like it belongs in another century.
Finally, hit the Westport Museum for History and Culture. They’ve done incredible work documenting the Fitzgeralds' time in the town. They have photos, maps, and even records of the couple's local scandals. It’s the best way to separate the myth from the reality.
Actionable Insights for the Literary Traveler
If you want to dive deeper into the real Gatsby in Connecticut: the untold story, here is how you do it right:
- Read "The World's Fair" by E.L. Doctorow or the essays of Barbara Probst Solomon. They provide the academic and personal weight to the Westport claim.
- Visit in the late summer. You need that oppressive New England humidity to really understand why the characters in the book are so on edge. The heat is a character in The Great Gatsby, and you won't feel it the same way in the spring.
- Check the local property records. If you're a real nerd, the Westport town hall has records dating back to the 20s. You can see exactly who owned what and how the estates were partitioned.
- Look for the "Old Money" markers. Notice the difference between the stone walls of the 18th-century farms and the ornate gates of the 1920s estates. That's the visual language of the book.
The real story of Gatsby isn't just a story about a guy who liked a girl. It's a story about a guy who wanted to belong to a world that didn't want him. Fitzgerald felt that exact same way when he was living in that little gray house in Connecticut, looking at the lights of the Lewis estate. He was Nick Carraway, and he was Jay Gatsby, all at once. And he was doing it in Westport.
Long Island can keep the movies. Connecticut has the truth.
To truly understand the landscape, grab a copy of the 1922 edition of the Westport Town Directory. It lists the residents of the era, including the staff at the major estates, giving a glimpse into the hidden class hierarchy that Fitzgerald captured so perfectly. You’ll see names that sound suspiciously like characters in the book—people who lived and worked in the shadow of the real West Egg. Once you see the map of 1920 Westport, the geography of the novel finally makes perfect sense.