Gatsby’s guide to Long Island

Illustrations: Vicki Turner

Aged only 28 when The Great Gatsby was published on 10 April 1925, F Scott Fitzgerald considered his third book to be “about the best American novel ever written”. Sales and critics initially disagreed, but the story has become an iconic text over time, spawning numerous adaptations on stage and screen.

A century later, its themes – the American Dream, hopeless romanticism, celebrity and class – continue to influence culture. Enigmatic Jay Gatsby has been dropped into Taylor Swift lyrics, used in product branding and even inspired popular online memes. And Long Island – the playground for the novel’s glittering characters – still echoes with his influence, too. Want to feel the energy for yourself? Capital idea. Simply drop in at these spots, old sport…

Gateway Drive, Great Neck

The Fitzgeralds and their baby daughter lived at number 6 on this residential street in Great Neck – what would become ‘West Egg’ of the novel. While the old-money families resided across the bay, the couple partied with neighbouring authors and actors (keeping a budget ledger of expenses that included ‘household liquor’ and ‘wild parties’). Fitzgerald wrote three chapters of his novel in the room over the garage in 1923, finishing it in the south of France. It’s a private home now, but worth a respectful ogle.

Oheka Castle and Falaise

Long Island was littered with ‘Gold Coast Mansions’ in the 1920s, with turreted Beacon Towers the apparent inspiration for Jay Gatsby’s lavish abode. While that has been demolished, many such homes remain, including opulent French-style hotel with formal gardens, Oheka Castle, and the former home of Harry Guggenheim, Falaise, on the pretty Sands Point Preserve. Both offer regular tours of their Gatsbyesque grounds and glitzy interiors and, in the case of Falaise, a peek into the room where another wealthy man got a rude awakening – it’s the location of the horse’s head scene in The Godfather.

The Hamptons

King’s Point was the model for Gatsby’s shore but celebrities now flock to the Hamptons – especially for Michael Rubin’s annual star-studded 4th July party. If you’re not expecting an invite to that ultra-exclusive soirée, you can still rub shoulders with the famous as they shop at the farmers’ markets or grab coffee in many of the Hamptons’ picturesque towns. Hotspots include restaurants such as Nick & Toni’s in East Hampton, The Surf Lodge in Montauk and Topping Rose House in Bridgehampton. There are also hamlets including Amagansett where Gwyneth Paltrow has a house, Water Mill (where Jennifer Lopez resides) and Sag Harbor (where Justin Timberlake had his recent driving mishap).

Great Gatsby Boat Tour

The homes of the rich and famous are difficult to spy from the road, but bobbing about on the Sound gives plenty of shoreline opportunities for snooping. Narrated by a member of the F Scott Fitzgerald Society, this two-hour boat tour, operating from Port Washington from May through to September, takes in the spots and vistas that inspired the writer. Some outings will offer special events this summer to tie in with the book’s centenary.

The Jazz Age Lawn Party

Now in its 20th year, this annual ticketed flapper-filled event on Governors Island lawn in New York Harbour gives a taste of Gatsby’s blue garden, where “men and girls came and went like moths among the whisperings and Champagne and stars”. Live jazz, Charleston dancers, vintage cars and retro cocktails are available this summer to costumed ferry-hoppers arriving from Brooklyn and lower Manhattan. Running from 11am-5pm on 14-15 June and 9-10 August, the events’ rules are simple: only ticketed guests on the island, no bootlegging and cosplay is strongly encouraged.

The Plaza Hotel, Manhattan

If you feel the need to “go to town” like socialite Daisy Buchanan, head to this 1905-built Manhattan institution in a prime position on Central Park. It was such a favourite of Fitzgerald that Ernest Hemingway joked that the author should donate his liver to Princeton and his heart to the Plaza. (Fitzgerald’s wife, Zelda, once frolicked in the Pulitzer fountain opposite the hotel.) A tipple in the Champagne Bar or afternoon team in the glass-roofed Palm Court have a Prohibition-era feel, and the elegant suites still offer room service for anyone wanting a “showdown” in the manner of Fitzgerald’s book. Rent the one-bedroom ‘Gatsby suite’ if you’re feeling careless.

Getting there

Be like Great Gatsby narrator Nick Carraway and, from New York, take the Long Island Rail Road (LIRR) from Penn or Grand Central Stations on the Port Washington line to Great Neck and Manhasset. Or drive there on the Long Island Expressway. Yellow Rolls-Royce is optional.

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