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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.

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