Celebrate 100 years of The Great Gatsby with a trip to the ritziest hidden gems in New York State

Live the high life like Jay Gatsby with these must-visit old-world-charm destinations in New York State
Boldt Castle by the river
Photograph: Supplied | I LOVE NY | Boldt Castle, Thousand Islands-Seaway, New York State
By Caitlyn Todoroski for Time Out in partnership with ILOVENY – the Official Tourism Office for New York State
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Ahhh, New York, New York. It’s not the first – or last – time the magical state will be referenced in music and literature, and for good reason. As Frank Sinatra would be pleased to hear, we’re ‘spreading the news’ of New York State’s best hidden gems and accommodation options. The twist? This travel inspo is for the glamour lovers; each of these destinations will make you feel like you’ve stepped into the pages of Scott Fitzgerald’s classic, The Great Gatsby. Being the novel’s 100th anniversary, we say there’s no better time to jet off to the Empire State. And while you’re at it, get there with Delta Air Lines, who also happen to be celebrating its 100th birthday.

Explore New York State

Where to stay

While Australia’s Gold Coast is a place for sunshine, social media influencers and surfers, New York’s version is a far cry. The north shore of Long Island was nicknamed the Gold Coast when the beginning of the 20th century saw an eye-boggling amount of extravagant properties spring up. Oheka Castle is one of them, and it’s said to have inspired the Gatsby mansion. 

If you’re closer to the core of the Big Apple, you can check out the scene of Jay Gatsby and Tom’s heated confrontation at the ritzy Plaza Hotel (the pinnacle of Art Deco). 

In the Hudson Valley, the Mohonk Mountain House is an unbelievably picturesque resort set right on top of Mohonk Lake. It’s been operating since 1869 so they know a thing or two about 1920’s inspired old world charm with roaring fireplaces and lush carpets. 

Venture even further with the rustic-luxe collection of Adirondack Great Camps, or the meticulously curated Inns of Aurora in the Finger Lakes. 

Journey beyond the city that never sleeps for one of these stays that’ll make you feel like you’re neighbours with Gatsby, or even better, a guest at his lavish estate.

Where to eat and drink

Oysters and seafood symbolise old money, class and indulgence in the world of The Great Gatsby, so make like an aristocrat and feast on a seafood extravaganza. Long Island is home to a multitude of historic oyster bars like The Cove, Salt & Barrel and Catch Oyster Bar, which dish up fresh shellfish and chilled Champagne.

New York City is the capital of speakeasies, but you can enjoy a luscious late-night tipple all around the state. The Hudson Valley is home to the intimate Back Bar and The Maker Lounge for a fun night out. Step back in time with the patterned wallpaper of The Gypsy Parlour, or the dim lights of High Violet in Buffalo.

If you like your drink with a side of smooth jazz, New York does live music best – at haunts like NYC’s Birdland, Smoke Jazz Club and Village Vanguard. Bonus points if you order a Gin Rickey.

What to do and see

Get a taste of the luxe life sailing the Thousand Islands. The archipelago is sandwiched between New York and Canada and features dazzling stops like Medieval-like Boldt Castle, and the magical Singer Castle perched on its own miniature island. If you like having your fun with two feet on solid ground, make a day of it at the Saratoga Racecourse – one of the US’s oldest major sporting venues. Raise a toast at both like the glamorous Jay Gatsby himself – *cue Leonardo DiCaprio raising a glass*.

There’s no more electrifying venue to catch a show for a cultural rendezvous than a restored venue like Albany’s grandiose Palace Theatre, or Schenectady’s palatial Proctors Theatre. And, of course, Fitzgerald’s novel has also been adapted into a vibrant musical that you can catch on Broadway in NYC.

Must-visit literary lover locations

It’s not just The Great Gatsby that takes inspiration from New York. Mark Twain’s famed Tom Sawyer and Huckleberry Finn adventures were written from his eccentric octagonal study in the lush Finger Lakes; while the Sleepy Hollow Cemetery in Hudson gives a behind-the-scenes look at Washington Irving’s short horror story.

The life’s work of one of America’s most influential poets is compiled at the Walt Whitman Birthplace State Historic Site on Long Island. Everything from recordings of the poet’s voice from the 1800s to original letters, artefacts and manuscripts can be found here. 

If memorabilia is your jam, you’ll love the All Things Oz Museum in Central New York. Everything from Judy Garland’s autographs to munchkin costumes can be found here – but the main event is the annual Oz-Stravaganza festival in June, featuring a parade – oh my!

Fly to New York with Delta

Like The Great Gatsby, Delta Air Lines is also celebrating its centennial year. The global airline connects Australia to New York – and more than 50 other destinations worldwide – via a seamless connection in Los Angeles. There are four levels of service to strap in for: ranging from main cabin and cruising all the way up to its Delta One Suites for the (very) high life. You won’t be bored – more than 1,000 hours of complimentary in-flight entertainment is waiting for you – as is a fresh seasonal menu. As Sinatra would say, “Come fly with me, let’s fly, let’s fly away”.

Learn more about exploring New York State here.

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