A Gatsby-inspired adventure in New York State

Indulge in adventures straight out of The Great Gatsby with a twirl around the palaces and parklands of New York state, writes Kris Griffiths

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As the steep gabled roofs of a fairytale castle loom ahead of us and gravel crunches beneath the car wheels, I get a taste of how The Great Gatsby narrator Nick Carraway felt when approaching Jay Gatsby’s Long Island manor for the first time – awestruck at how the other half live.

With the centenary of F Scott Fitzgerald’s seminal novel this year sparking renewed interest in the Roaring Twenties, I’ve come to New York state with a group of US specialist operators to explore the places and experiences at the heart of Gatsby’s world.

Oheka Castle

Oheka Castle, the colossal estate where we’ve just arrived, was reportedly Fitzgerald’s primary inspiration for the Gatsby estate and the lavish functions thrown there. At the time of its construction in 1919, the 127-room Oheka (a portmanteau name created by its owner, the financier Otto Hermann Kahn) was – and remains – the second-largest private residence ever built in America.

In the ensuing decade, it hosted the hottest-ticket parties in the region, attracting a who’s who of Hollywood stars, political luminaries and European royalty.

Oheka’s interior design director Nancy Melius points out the similarity between Kahn and Jay Gatsby. Kahn also liked to go large, ensuring his castle sat on the tallest point on Long Island.

“He and his construction team had to create a new hilltop location for Oheka from scratch,” she says. “It took all of 1915 and 1916 for workmen and horse-drawn wagons to haul the dirt necessary to achieve the supreme elevation he desired, with a view of the Long Island Sound two miles away.”

Today, it’s a prestigious hotel and wedding venue, with the landscaped setting a backdrop to Oheka’s annual black-tie garden party, A Great Gatsby Affair. For those who don’t make the VIP guest list, a Gatsby Hour is held every night in the bar for both guests and nonguests to admire its grand interiors.

Gilded Age glamour

It was a late-19th-century period of conspicuous consumption and unbridled capitalism, known as the Gilded Age, that gave rise to these extravagant estates. The HBO series of the same name, written by Julian Fellowes, depicts the decadence in delicious detail – and, as a further selling point for the region, is set to return to screens this year.

Fittingly, a Downton Abbey (also written by Fellowes) vibe pervades properties in New York state. Old Westbury Gardens is modelled on an English manor house and is home to more than 800 hectares of gardens and woodland, making it a must for walkers and nature lovers.

Then there is Dutchess County’s Staatsburgh (pictured above): a 79-room beaux arts mansion overlooking the Hudson River and tree-covered Catskill Mountains, completed in 1895 by President Herbert Hoover’s treasury secretary, Ogden Mills.

The neoclassical pile looks not unlike the White House from the outside, and its 18-metre marbled dining room is opulent enough to host the loftiest of state banquets.

Dawn Hopper, managing director of tourism market development at Dutchess Tourism, says: “Just like Jay Gatsby, Mrs Mills – Ogden’s wife – threw a big society party here every weekend. If you got invited, it was a hell of a big deal.”

Finally, there’s Lyndhurst Mansion (pictured below), which abuts the Hudson. The property’s executive director, Howard Zar, says: “We’re the first Gothic house in the US, and the architect copied elements from British Gothic and Tudor structures.

“What makes a visit here easy is we’re the closest Hudson Valley great estate to New York City, so if tourists want to visit without renting a car and changing hotels, the train ride from Grand Central station is about 40 minutes.”

New York state of mind

If clients would like to get even more Gilded Age glamour into a stay, suggest trips to towns such as Troy, with its unspoiled 19th-century architecture, and Saratoga Springs, the state’s summer capital in the 1900s.

At the latter, restorative mineral waters, sumptuous buildings and gambling outlets (such as the impressive Canfield Casino, which is now a museum) made it a playground for New York’s moneyed elite.

Speaking of museums, standouts include the Vanderbilt Museum, combining a European-style manor with a planetarium and natural-history exhibition, and the FDR Museum, which immerses clients in the Roosevelt presidency, from the Great Depression to the Second World War.

Even an unassuming stonebuilt church, the Union Church of Pocantico Hills near Sleepy Hollow, has a little grandeur. It houses the final work of Henri Matisse – a stained-glass rose window painted just two days before his death in 1954.

For road-trippers, it’s worth a visit en route to Kykuit, another gargantuan manor that comprises a classical villa filled with paintings and sculptures (including works by Warhol and Picasso) plus 1,360 hectares of hillside land. It’s no surprise that its original owner, oil baron John D Rockefeller, was the world’s first billionaire.

The group caps off this tour of American heritage with a final night in the Gilded Age epicentre, New York City. We stay at The New Yorker in midtown Manhattan. The 43-storey art deco monolith was once the world’s tallest building, with 2,500 guest rooms.

These days, it’s just over 1,000, but it retains the period decor, including an ostentatiously gilded lobby.

“Can’t repeat the past? Why, of course you can!” declares Jay in one of The Great Gatsby’s most memorable lines. One thing’s for sure – history remains very much alive in New York state, ready for visitors who want to experience their own Roaring Twenties in the 2020s.

Book it

America As You Like It offers a 13-night Long Island, Hudson Valley, Central New York State & The Catskills itinerary from £1,695. The price includes flights, room-only accommodation and car hire, and is based on an October 2025 departure.
americaasyoulikeit.com

Insider insight

Maggi Smit, managing director, America As You Like It

“This tour had so many highlights. Old Westbury Gardens was beautiful, and the Suffolk County Vanderbilt Museum was fascinating. We enjoyed a memorable lunch at Oheka Castle, while the Union Church of Pocantico Hills with its Marc Chagall windows and Matisse’s last work was spectacular. Another highlight was learning about Saratoga’s horse-racing history, as well as Troy, which had a bustling Saturday market.”

Mark Sykes, North America and Caribbean product manager, Freedom Destinations

“I enjoyed exploring the Gilded Age mansions and ornate gardens throughout the countryside, seeing how they offer such a contrasting experience to Manhattan’s neon lights. Places such as Saratoga Springs keep things up to date with craft breweries, farm-to-table dining and boutique shopping. With easy access from the UK, New York state makes for an exceptional self-drive or rail holiday.”

Where to stay

Hilton Long Island, Huntington

In the heart of Long Island, just a mile south of the NY Interstate 495, this upscale hotel affords easy access for Oheka Castle, the Hamptons and New York City. Rooms start at $239 per night.
hilton.com

Inn at Bellefield, Hyde Park

This Marriott-operated venue’s spacious suites feature full kitchens and attentively appointed living spaces. It sits handily opposite The Culinary Institute of America, where you can enjoy a delectable luncheon fit for Daisy Buchanan. Rooms start from £115 per night.
travelagents.marriott.com

Westchester Marriott

With 444 rooms across 10 floors, this is one of Westchester County’s largest hotels, and a convenient base for historic sites up and down the Hudson Valley. Rooms lead in at £132 per night.
travelagents.marriott.com

PICTURES: Phillip Ennis Photography; Karl Rabe; Clifford Pickett