Explore the decadent mansions of the moneyed north shore of New York’s Long Island, which served as the setting for F Scott Fitzgerald’s classic American novel.

Mansions with more rooms than there are US states; gleaming automobiles tearing along open country roads; chic and bejewelled ladies sipping champagne and gin rickeys from crystal glasses while sitting poolside on a hot summer day. These are the images that come to mind when thinking of F Scott Fitzgerald’s classic story The Great Gatsby, among the most admired and well-loved books in the pantheon of American literature.

Published in 1925, the book chronicles the provincial events of 1922 for a set of Long Island-living New Yorkers who are as consumed by the past as they are by the trappings of their wealth. As a salve to their particular sort of ennui, they surround themselves with carelessly collected riches. While many people today use the term “Gatsby-esque” to describe a dreamy and fantastical type of 1920s-style aesthetic, Fitzgerald’s tale actually cuts unsparingly like a surgeon’s scalpel into the centuries-old US obsession with wealth, power, status and money.

Although the intervening decades have done much to alter the landscape that Fitzgerald wrote so lovingly about, there are still many sites that evoke the bygone era of Long Island’s “Gold Coast” – the nickname for the moneyed north shore of Long Island that extends east of New York .

Fictional mansions
Fitzgerald set his masterpiece in the fictional bayside villages of West Egg and East Egg, which seem to geographically correlate to the real-life communities of Great Neck (West Egg) and Port Washington (East Egg). The towns match the author’s description of the twin peninsulas as “a pair of enormous eggs” that “jut out into… the great wet barnyard of Long Island Sound” about 20 miles from Manhattan.

Just as there is no true West and East Eggs, there are no authenticated stand-ins for the mansions of Jay Gatsby and Daisy Buchanan, the star-crossed lovers at the centre of the novel. Many thought the recently demolished Land’s End estate near Port Washington was a model for the “red-and-white Georgian Colonial mansion” that was home to Buchanan and her hulking husband, Tom, but sadly it was lost in 2011 to the ever-encroaching development of subdivisions and McMansions. As for Gatsby’s palace of the damned, no such place exactly exists, although a handful of sites that evoke the ritzy ambience of the eponymous bootlegger and his gilded brethren are available to visit.

Long Island high life
One of the finest and best-preserved Gold Coast mansions open to visitors is the stunningly beautiful Westbury House at Old Westbury Gardens. A true Long Island highlight, the 1906 estate was home to Jay and Margarita Phipps, a wealthy industrialist and his English wife, until the 1950s. The lush Charles II-style manor is stuffed with European antiques from the family’s collections and is set on more than 200 acres of manicured grounds that include ponds, a walled garden, a cottage garden with children’s playhouses, a primrose path, an area called the “Ghost Walk” and boxwoods galore.

Even though the estate is located in Old Westbury, about 10 miles from Port Washington or Great Neck, the house provides a fabulous example of the jaw-dropping Gold Coast decadence that Fitzgerald wrote about.  Film fans may recognise the grounds from movies as varied as Love Story, North By Northwest, The Age of Innocence and To Wong Fu, Thanks for Everything, Julie Newmar. Well worth a visit, the estate closes after the Christmas holidays and reopens to the public every April.

Less meticulously maintained but still of considerable interest is Hempstead House on the Sands Point Preserve near Port Washington. The massive castle-like structure was the early 20th-century home of Daniel Guggenheim (brother of the noted modern art enthusiast Solomon R Guggenheim). Despite its gothic overtones, the manor has soaring views across the sound to Connecticut, making it highly evocative of a place where Gatsby might have stared out over the water at the green light of Daisy’s dock. As a matter of novelistic accuracy, however, this area was more likely a stand-in for the old-moneyed East Egg in the novel, while the arriviste nouveau riche estate of Gatsby was probably located across Manhasset Bay in Great Neck (West Egg).

The beautiful vistas at Hempstead House are surrounded by the various trails cutting through its former grounds, now a 216-acre nature preserve. While the house is unfurnished and not open to visitors, the preserve, open year round, is an appealing place for hiking and picnicking.

In the nearby town of Roslyn is the William Cullen Bryant Nature Preserve, home to the Nassau County Museum of Art. Housed in the exquisite Bryce-Frick mansion (built in 1900 by General Lloyd Bryce and purchased by Childs Frick, son of steel magnate Henry Clay Frick, 19 years later), the charming museum hosts a variety of changing exhibitions featuring the likes of Catalan painter and sculptor Joan Miro and African-American painter Jean-Michel Basquiat. The real appeal, though, is the contemporary sculpture garden that stretches out across the wide lawns, with works by Mark di Suvero, Alexander Calder, Richard Serra and many more lesser-known, but no less thrilling artists. Another glorious example of the Gold Coast excess described in the novel, the house is complemented by the many trails of the preserve leading to lovely harbour views and the occasional sighting of a red-tailed hawk.  

Another prime site that recalls this glamorous and unique past is the Vanderbilt Museum in Centerport, Long Island. At the eastern edge of the Gold Coast, about 25 miles from Great Neck, this 24-room Spanish-style estate was home to William K Vanderbilt II, great-grandson of the famed railroad industrialist Cornelius Vanderbilt. The Vanderbilts, one of the most prestigious families in America, were the sort of social barons that Gatsby longed to emulate. The common lineage of Fitzgerald’s antihero (born in the Midwest to working class parents) is something he could never overcome and, in some ways it led to the character’s tragic, waterlogged fate. Visitors who take the mansion tour will learn of the owner’s extravagant 1920s lifestyle, which included decadent parties attended by the most glamorous socialites of the era. 

The estate has been turned into an oddball museum dedicated to Vanderbilt, and a primary attraction is his collection of native arts and fauna (such as hundreds of taxidermy birds, including some extinct ones, displayed alongside shrunken heads and exotic tools). Other notable curiosities include a real Egyptian mummy and preserved giant lobsters – some weighing as much as 35lb. Everything inside the Eagle’s Nest mansion, with its spectacular high-perched views of the sound and Northport harbour, is original from its owner – a fantastic relic of millionaires with unlimited financial resources from days gone by.

An immersive Gatsby experience
Those with a sea-faring bent might enjoy the Great Gatsby Boat Tour (on Saturdays mornings from July through September before the weather turns too chilly). It cuts through the waters of Manhasset Bay between King’s Point near Great Neck and Sands Point near Port Washington, and glides past the various historical boathouses and mansions that inspired Fitzgerald, like the aforementioned Hempstead House as well as several other private homes. While much of what you see has been built up since Fitzgerald had his characters ran amok throughout the shore, it is an interesting look at the grandiosity with which the novel has become synonymous. Today there might be more speedboats than sailboats, or Range Rovers than Rolls Royces, but the tony, moneyed communities are much the same as in the 1920s.

Fitzgerald fans should also take a trip to 6 Gateway Drive in Great Neck, where Fitzgerald and his infamous wife Zelda lived from 1922 to 1924 while he worked on the novel. At the time, the cottage was modest compared to the glitzy mansions of his wealthy characters and neighbours, but the now extravagant private home has since been remodelled.  Those looking to visit the author and his wife today will need to head south to  Rockville, Maryland to find their eternal resting spots.

These sites are all close enough to New York City to be day-tripper friendly. If you are looking to spend the night in Jazz Age hotel, however, the best option is Oheka Castle. A French chateau-style home and one of the largest private residences built in the US, it was home to many swinging nights in the 1920s until its owner’s death in the 1930s. Today it has 32 hotel rooms, fine dining, formal gardens, a spa and golf, and is a gorgeous place to conjure Gatsby for the night.