Through Gatsby’s eyes: New York’s Jazz Age gems

The Great Gatsby is a classic American novel and a continual inspiration to artists of all kinds. We've uncovered New York City and Long Island sights from F. Scott Fitzgerald's most iconic work.

Prohibition is passé and Art Deco is long dead, but even though we're in a new era of the Roaring 20s (the 2020s), we're still up for any chance to escape back to a time when lively flappers and speakeasies ruled the land.

Here are our favorite spots that harken back to the original Roaring 20s (the 1920s) in New York today, where you'll be toasting with gin, living the suite life and partying it up until the wee hours of the morning in style.

Take a Nick Carraway walk through Manhattan

There’s no other city like New York when it comes to people-watching, and Nick Carraway was the novel’s primary voyeur, ambling through the city streets. Take a nighttime stroll, starting where the narrator lunched at the Yale Club on Vanderbilt Avenue at 44th Street. Stop in for a decadent cocktail at The Campbell Bar (formerly the Campbell Apartment Bar), the restored 1920s club inside Grand Central Terminal, which glows like the gilded age. Be sure to dress the part as this upscale bar doesn't allow t-shirts. Then follow his route south down Madison Avenue and west to Penn Station. The city lights might twinkle more brightly than they used to, but you can still spy some Twenties charm, especially after a few rounds of gin rickeys at the bar.

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The suite life, The Plaza Hotel

F. Scott Fitzgerald and his wife, Zelda, often visited the Plaza in the 1920s, and the opulent New York hotel, with its unchanging historic façade on Fifth Avenue, was the setting for a feisty penultimate scene in the novel. If you can’t afford to stay in the newly designed, lavish Fitzgerald Suite, stop in for Afternoon Tea at The Palm Court, under the dazzling 1800 square foot stained-glass ceiling.

Get into the spirit of the Jazz Age Lawn Party, Governors Island

Hop a ferry to Governors Island – you’ll feel like you’ve stepped back in time when you arrive at this peaceful, green and tiny historic isle, only a 10-minute boat ride from Manhattan. Every summer, there’s a Jazz Age Lawn Party where New Yorkers have fun taking themselves very seriously in their finest flapper attire, suspenders and tennis whites. Be prepared to Charleston, shop for vintage clothes, promenade with a parasol and drink 'bootleg' style without raising an eyebrow.

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Bike over the Queensboro Bridge

‘The city seen from the Queensboro Bridge is always the city seen for the first time, in its first wild promise of all the mystery and the beauty in the world,’ notes narrator Nick Carraway as he and Gatsby cruise from Long Island into Manhattan. You probably won’t have a Rolls Royce to take in the skyline, so why not hop on a Citi Bike in Long Island City, and pedal your way along the bike path over the Queensboro (aka 59th St) bridge? There are plenty of opportunities to take a retro sepia-tone photo along the way. Check out NYC bike maps for all the best bike paths.

Long Island mansion tour, Old Westbury Gardens

Strung along Long Island’s 'Gold Coast' to tap into the inspiration Fitzgerald used to depict his character’s luminescent lives: 1920s mansions that might as well be castles. To check out the Gatsby-esque gargantuan estates, hop on the Long Island Rail Road from New York City and take a tour of the historic Old Westbury Gardens. You can check off a list of millionaire-worthy features: 200 acres of landscaped gardens with a rose garden, woodlands, ponds and lakes, a 70-room English manor house built in the early 1900s, lush antiques and impressive artwork all brimming with historic intrigue. Along with tours of the estate and gardens, there's a cafe in the woods, museum exhibits, classic car shows, indoor and outdoor concerts, Scottish games (of course) and master gardener and educator talks to educate the riffraff about horticulture, art, history and architecture.

For more mansion tours, visit Eagle’s Nest, the Vanderbilt Mansion turned museum and planetarium with picturesque views of the Long Island Sound, and the colossal Oheka Castle – the second-largest private residence in the US.

This article was originally published in May 13, 2017.

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