In search of
The Great Gatsby
It has been 100 years since F Scott Fitzgerald’s Jazz Age masterpiece The Great Gatsby was first published, yet the ‘Gold Coast’ mansions of New York State that inspired it have lost none of their lustre
Words Jacqui Agate
(Alamy)
Northport Bay shone like a slab of marble, the water’s surface veined with gold from a melting evening sun. The sky was raked with clouds and every boat in the harbour appeared twice: once in its solid form and a second time as a sparkling reflection. On the horizon, gargantuan homes cast their own images in the bay. I imagined that any one of them could have a green light burning at the end of its dock – one that a lovelorn Jay Gatsby might reach out for in vain.
I was in the small waterfront village of Northport, on Long Island’s North Shore, a region whose extravagant displays of wealth have earned it the nickname the ‘Gold Coast’. The area, with its twinkling early 20th-century mansions, storybook towns and heartstopping Long Island Sound views, is known as the inspiration for F Scott Fitzgerald’s The Great Gatsby, which is celebrating 100 years since its first publication this month (April 2025).
For me, the journey to New York State in search of the novel’s real-life locations was something close to a pilgrimage. I first read The Great Gatsby when I was a teenager and have returned to it almost every year since, hungrily scanning the pages for nuggets of wisdom, like a prospector panning for gold. My copy, whose cover features a doe-eyed Daisy Buchanan, is faded and dog-eared.
I’m not alone in my love for this classic novel, either. Today, Gatsby fever has reached a crescendo. In 2021, the book entered the public domain and a flurry of adaptations, from graphic novels to theatre plays, followed (succeeding Baz Luhrmann’s flamboyant 2013 movie). Right now, The Great Gatsby is the most sought-after ticket on New York City’s Broadway, while sites across the state are hosting special centenary celebrations.
It’s no wonder that the novel has such universal appeal. As it follows Jay Gatsby’s quest to win back the heart of affluent socialite Daisy Buchanan, the book takes a scalpel to the human condition. Love, hope and idealism clash with gross excess, egotism and the hollowness of the privileged classes. It holds a cracked mirror to American society, and its comments on class, racism and the fragility of the American Dream feel as precise today as they must have back then.
The Great Gatsby is equally a novel about a specific place and moment in time, and the Roaring Twenties glitter and rumble on the page. It is set in 1922, a time period sandwiched between two World Wars, in which the USA cemented its status as a global superpower, bolstered by booming manufacturing industries and the exploitation of natural resources such as coal and timber. It was also a time when prohibition laws failed to quell the flow of illegal liquor. As Fitzgerald wrote: ‘The parties were bigger, the pace was faster, the buildings were higher, the morals looser.’
Old Westbury Gardens is a popular location with filmmakers, and the estate has featured in many movies and TV series through the years, from Alfred Hitchcock’s North by Northwest to current HBO hit The Gilded Age (Alamy)
Egg hunt
The fictional Long Island peninsulas of ‘East Egg’ and ‘West Egg’ – likely based on real-life communities – drive the novel’s plot. The former is the domain of the old-money elite, such as the characters Tom and Daisy Buchanan, while the nouveau riche, including Gatsby himself, live on the adjacent West Egg.
Fitzgerald wrote: ‘Twenty miles from the city a pair of enormous eggs, identical in contour and separated only by a courtesy bay, jut out into the most domesticated body of salt water in the Western hemisphere, the great wet barnyard of Long Island Sound.’
Pore over a map of Long Island’s Gold Coast and you’ll make out a pair of peninsulas that fit Fitzgerald’s description. Divided by the Manhasset Bay, the misshapen spits of land known as Great Neck and Cow Neck are widely considered to be the real-life West Egg and East Egg. Even today, the novel is still a key driver of tourism to this mansion-stitched region.
Fitzgerald and his wife Zelda lived in Great Neck (‘the less fashionable of the two’) from 1922 to 1924. And while it’s not clear which, if any, of the remaining Gold Coast mansions the Fitzgeralds frequented, there’s no doubt that the sparkling lives of Long Island’s elite (a set that the Fitzgeralds were newly part of) served as a fertile muse for the book.
Leaving behind the boutique shops and seafood restaurants of my Northport base, I began by driving around Great Neck. The home the Fitzgeralds lived in – an elegant Mediterranean-style property – is privately owned and therefore not available for tours. The town’s main artery, with its modern restaurants and chic clothing stores, would have looked wildly different back in Fitzgerald’s day too. But I found a more tangible dose of the Gatsby era about a 20-minute drive east, at Old Westbury Gardens. This is just one of a string of historical estates collectively known as ‘The Great Gatsby Mansions’.
“All these wealthy people wanted to build great estates like they had in Europe”
Towering wrought-iron gates announced my arrival, opening out onto a swooping alley of linden trees. Eventually, a red-brick mansion came into view, with a yawning columned entryway and a façade licked with gold leaf. In the novel, Tom and Daisy’s East Egg pile is described as ‘a cheerful red-and-white Georgian Colonial mansion overlooking the bay’. While no single property is confirmed as the Buchanan mansion’s blueprint, this one feels about as close as you might get.
The Restoration-style home was designed by Englishman George A Crawley in 1904 and was owned by John Phipps and his wife Margarita. Tours offer insights into the mansion’s affluent proprietors, sharing a backstory befitting one of Gatsby’s party guests: John was the son of Henry Phipps, an industrialist who made his fortune in steel alongside the illustrious Andrew Carnegie.
They would have used the estate as a spring ‘cottage’, escaping to alternate residences in Palm Beach, Florida and New Jersey for the rest of the year. The grounds have more recently been used for filming an episode of The Gilded Age, an HBO series following the lives of America’s upper classes in the late 19th century.
“All these wealthy people wanted to build great estates like they had in Europe,” explained my guide, Paul Hunchak. “This is one of them. It was designed to look like an English estate, and [the owners] wanted it to be extremely authentic.”
We passed through a pair of heavy doors and were swallowed by a dark-wood-clad foyer. A ceiling fresco depicted a cloud-streaked blue sky, and a pair of cupids were carved into a colossal fireplace. A taxidermied stag looked out from the wall with gaping, glassy eyes.
The estate used English craftsmen as part of a major renovation project beginning in 2019, and the interiors are filled with antique objets d’art collected from English auction houses. If Fitzgerald’s pensive narrator Nick Carraway were to wander the halls, I imagine he’d be in awe of its beauty but quietly critical of its overt lavishness.
As I explored the tangle of rooms, I searched for whispers of Gatsby – and I found one soon enough. Hanging in a heavy golden frame was a work by master portrait painter Joshua Reynolds, depicting Henry Scott, third Duke of Buccleuch and his siblings, whom Nick Carraway claims to be descended from in the novel. Hunchak also explained that the famous polo player Tommy Hitchcock Jr, the inspiration for the character of Tom Buchanan, was a friend of the family. It was a reminder of the thin thread between Fitzgerald’s fiction and his reality, and how these mansions keep fragments of the novel and the past alive in glittering material form.
Northport Bay is part of Long Island’s so-called ‘Gold Coast’, whose mansions recall a time when this was the playground of the USA’s wealthiest capitalists (Alamy)
The neverending party
Although the Old Westbury Gardens mansion looks the part, Hunchak explained that the “genteel and old-school” Phipps family were not fans of large parties. The same cannot be said for Otto Hermann Kahn, the proprietor of the sprawling Oheka Castle, around 16km to the east, in Huntington.
‘It was a factual imitation of some Hotel de Ville in Normandy, with a tower on one side, spanking new under a thin beard of raw ivy,’ Fitzgerald wrote of Gatsby’s West Egg mansion. The French-château-inspired Oheka Castle, with its towers and turrets, roughly fits the description, right down to the sheet of ivy crawling up the façade.
“It’s the second-largest private home in the country, after Biltmore in North Carolina,” said tour guide Vicky as she led me through a cavernous dining room decorated with heavy taupe-coloured drapes and jewel-encrusted chandeliers. “Kahn wanted his mansion to be at the highest point on Long Island… but that was taken. So, for two years, he had soil trucked in to raise this plot to the highest point. That’s why you can see the water.”
Indeed, through the giant windows I could make out the yacht-studded Long Island Sound. Kahn’s extravagant deed struck me as more than a little Gatsby-esque. He was a wealthy banker, who was heavily involved in the railroad industry and a keen art collector. Though the property is now filled with reproductions, the marble busts, Italian landscape paintings and regal portraiture give the rooms a gallery-like feeling.
“You might know the names of some of Otto’s contemporaries,” Vicky said. “The Vanderbilts, JP Morgan, and John D Rockefeller, who owned the Standard Oil Company and was the country’s first billionaire. Think Taylor Swift or Jeff Bezos.”
“Oheka Castle is the second-largest private home in the country”
The property was also the setting for giant Gatsby-style parties, drawing Hollywood stars such as Charlie Chaplin and a ‘who’s who’ of New York’s elite and creative classes, including the composer George Gershwin.
“The lavish parties that were depicted in The Great Gatsby were loosely based on the parties that Otto Kahn threw here,” said Vicky as we peeked into a wood-panelled room, its shelves heaving with leather-bound books. Meanwhile, Otto’s wife, Addie, despised her husband’s excess: “She called it ‘Otto’s Zoo’.”
The mansion has been a draw for modern-day stars too. Everyone from Nicole Kidman to Justin Timberlake has visited the site, which now doubles as a fine hotel. It was also the setting for Taylor Swift’s ‘Blank Space’ music video, filmed in 2014. The mega-star sings from the top of a wrought-iron-clad staircase and rides snow-white horses through the formal French gardens, originally designed by the revered Olmsted Brothers.
Today, the mansion is on the National Register of Historic Places (“As well it should be,” Vicky chimed), but its future wasn’t always certain. From 1948, the Eastern Military Academy occupied the property, destroying the gardens. When it left in the 1970s, the mansion stood hollow and abandoned. If a private developer hadn’t purchased it in 1984, it may have faced the wrecking ball.
That’s true for many of the Gold Coast’s sparkling estates. Between the late 19th century and the 1930s, there were more than 1,000 mansions here; today, less than a third survive. However, the public’s enduring love for The Great Gatsby might help to save these building blocks of American history.
Oheka Castle reputedly cost Kahn US$11 million to create, with a chunk of this sunk into the Gatsby-esque folly of raising the land so that he could have the highest vantage point in the area (Alamy)
The glittering apple
“Doing a Fitzgerald tour, I often meet superfans,” said Kevin Fitzpatrick, an author, Fitzgerald buff and guide on the Great Gatsby Boat Tour, which sweeps across Manhasset Bay. “You can see the looks on people’s faces when we say: this is Port Washington (Cow Neck) – this is East Egg. Over there is Great Neck – that’s West Egg.”
On Long Island, I’d made a last visit to Sands Point Preserve, a sprawling estate at the very tip of East Egg (Cow Neck). I toured Falaise Mansion, a French-style property built in 1923 by magnate Harry Guggenheim, and looked over the rippling Long Island Sound from a perfectly positioned bench. There was time for a quick tour of Port Washington, Cow Neck Peninsula’s main community, with its dockside seafood spots and down-to-earth bars; then I hopped on the Long Island Railroad and hurtled towards New York City to meet Kevin. We sat down at the Algonquin Hotel, a known haunt of New York’s Jazz Age literati, including the Fitzgeralds themselves.
“When you’re on the train going through Queens, by the baseball fields, that’s where the ‘Valley of Ashes’ was,” Kevin explained, speaking of the bleak, polluted industrial wasteland between Long Island and Manhattan that Fitzgerald describes in the novel. Today, the land has been transformed into the lush Flushing Meadows Corona Park. In the book, it symbolises the dark side of America’s economic explosion.
“Everything was booming, including the railway network. But at the same time, there were a lot of problems: a lack of equal justice, division of classes, racial intolerance, the treatment of Native Americans. All of that was being swept under the rug,” Kevin said.
Indeed, The Great Gatsby is intensely critical of the upper classes’ ‘vast carelessness’, and several of my tour guides had spoken of the fierce divides between rich and poor during the 1920s. At this time, just 5% of the USA’s elite made a third of all its income; meanwhile, two-thirds of the population existed below the poverty line. However, despite Fitzgerald’s reproval of America’s upper classes, the author had a foot in that world himself – particularly in New York City.
I had read The Great Gatsby long before I visited its setting. The Big Apple in those pages seemed to be one of glittering promise and morbid decadence. It was a city that needn’t sleep, for it dreamt big enough in its waking hours; a place where booze-blurred parties spiralled in hotel suites and speakeasies swirled with jazz. It was a place so swollen with life that even the fast-multiplying skyscrapers couldn’t contain it.
It is no less full of vitality today. New York is one of the most touristed places in the world, with upwards of 64 million visitors each year. Kevin whisked me past the Beaux-Arts-style Scribner Building, where the novel’s original publisher, Charles Scribner’s Sons, was located, and into the Plaza Hotel, a favourite hangout of Scott and Zelda’s and the setting for one of the novel’s most climactic scenes. Today, a Gatsby-themed suite milks the literary connection, and it has become endlessly popular with Fitzgerald fans.
“The novel is so successful because it’s ultimately about what makes us human,” Fitzpatrick said as we walked under the glimmering stained-glass skylight of the hotel’s Palm Court. “It’s about love, it’s about loss, it’s about class. That’s why the novel is so universal.”
As love for Fitzgerald’s classic story endures and expands, curiosity about its twinkling setting will likely grow too. Long Island’s Gold Coast and the skyscraper-sewn boulevards of New York City capture the elusive spirit of the era in the same way Fitzgerald’s prose does – with all its layers and contradictions, its darkness and light. To visit is indeed to be ‘borne back ceaselessly into the past’, as Fitzgerald wrote, but you’ll also get a glimpse into the people, the places and the period that birthed modern America.
Follow in Fitzgerald’s footsteps
Montgomery, Alabama
Head to the Alabama state capital, where F Scott Fitzgerald’s wife, née Zelda Sayre, was born, and where the couple lived for a short time in the early 1930s. A literary tour will take you to the Alabama State Capitol – on the steps of which a young Zelda played as a child – and to Chris’ Hot Dogs, a fast-food joint frequented by the pair.
The city’s bookish highlight is the Scott and Zelda Fitzgerald Museum, which occupies the home the couple lived in while in Alabama. You can even stay in it overnight, as the upper floor has been transformed into a pair of suites with echoes of the Jazz Age.
Louisville, Kentucky
F Scott Fitzgerald was stationed at Louisville’s former military base, Camp Taylor, during the First World War. It’s said that he would often prop up the bar of the Beaux-Arts-style Seelbach Hotel. It has been suggested that the colourful characters Fitzgerald met at the hotel bar inspired The Great Gatsby’s bootleggers. The city will mark the novel’s anniversary with a string of special events. The Seelbach also plans to open a new Gatsby-inspired suite.
Westport, Connecticut
The coastal town of Westport – across the Sound from Long Island’s mansion-dotted North Shore – has been floated as another muse for Fitzgerald’s ‘Eggs’. After they were married, Scott and Zelda spirited away to this waterfront bolthole, renting a small home in town. A young, party-loving millionaire named Frederick E Lewis, who lived close to the Fitzgeralds during this time, has been suggested as one inspiration for Jay Gatsby. Decide for yourself while exploring the town’s beaches, independent-store-packed Main Street and contemporary art gallery.
Opposite: The Algonquin was a haunt of New York’s Jazz Age literati, including Dorothy Parker and the Fitzgeralds (Alamy)
The historical buildings of Northport (Alamy)
Need to know
When to go
Spring and autumn are fine times for a trip, with mild temperatures and fewer visitors frequenting Long Island’s lavish estates. You can also expect to see some bursts of fall colour in the parks and mansion grounds from late September. New York City bustles year-round.
Getting there and around
Both London Gatwick and Heathrow have daily direct flights to New York City’s John F Kennedy International Airport, while the latter also flies to Newark Liberty International Airport. Flights cost from about £305 and take around eight hours.
You can catch the Long Island Railroad from Penn Station to Long Island hubs, including Port Washington and Great Neck. A rental car provides extra freedom.
Where to stay
The boutique Northport Hotel makes a stylish base for exploring Long Island’s North Shore (from £323pn), centring you within the shops and restaurants of its quaint namesake. Or embrace the Gatsby theme at Oheka Castle, which has 34 luxurious rooms and suites (from £391pn). There’s endless choice in New York City proper, where The New Yorker (from £260pn), an Art Deco jewel built in 1929, captures the true spirit of the Jazz Age.
The trip
The author’s trip was supported by the New York State Division of Tourism.
Falaise Mansion is one of a pair of early 20th-century homes open to tours at Sands Point Preserve (Alamy)
