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Home / Travel

Holidays outside of New York City: Leave the Big Apple and step back to the Gilded Age

By Alex Mitcheson
NZ Herald·
7 Feb, 2025 06:00 AM7 mins to read

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Escape the buzz of NYC for a journey through Long Island’s gardens, Sleepy Hollow’s legends, and Saratoga Springs’ wellness retreats. Photo / Unsplash

Escape the buzz of NYC for a journey through Long Island’s gardens, Sleepy Hollow’s legends, and Saratoga Springs’ wellness retreats. Photo / Unsplash

Many people visit New York City, but few venture further into the state itself. Alex Mitcheson steps away from The Big Apple for a resplendent Great Gatsby-style tour of Long Island and Westchester.

It takes a while for the frenetic energy of Queens to subside and for the continuing greenery of Long Island to take over. I’ve left John F. Kennedy International Airport, and unlike most short and long-distance passengers, I’m heading east and away from the largest metropolitan area in the US towards an island with a difference.

The backdrop to one of America’s best-known pieces of literature, Long Island, with its portrayals of grandeur through F. Scott Fitzgerald’s The Great Gatsby, depicts a time when hedonistic partying was the status quo. Today, it is a vibrant, contemporary part of New York with enclaves of storied history.

READ MORE: What to see and do in Brooklyn, New York

An aerial view on Manhasset Bay in Long Island, New York state. Photo / Getty Images
An aerial view on Manhasset Bay in Long Island, New York state. Photo / Getty Images
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Nursing jetlag at 10am and sipping a takeaway coffee, gin and revelry are the last thing on my mind as I wander into Old Westbury Gardens. Largely untouched from the original 1906 design, the estate is an ode to Carolean Revival design popular during the reign of Charles II. Roses and rarer foxgloves frame gravel pathways punctuated by ornate seating areas. I sit and watch butterflies chase one another, realising this scene remains utterly unchanged from 120 years previous. A living, breathing, foliage-filled time capsule.

My French Dip sandwich at the OHK Bar & Restaurant at Oheka Castle doesn’t quite fit the incredibly palatial surroundings. Between manicured lawns and ornate glass doors flooding the dining room with dewy light, my dish’s saving grace is its perfectly cooked filet mignon filling: utterly delicious. One of the Gold Coast’s most illustrious mansions — and once the second biggest private residence in the country — it’s believed Fitzgerald’s Jay Gatsby is based on the self-indulgent German banker who built the property in 1919. Before leaving, I wander the grounds and marvel at symmetrical ponds and gallery-sized rooms.

Oheka Castle on Long Island is believed to have inspired Jay Gatsby’s mansion and has appeared in music videos and films.
Oheka Castle on Long Island is believed to have inspired Jay Gatsby’s mansion and has appeared in music videos and films.

There’s a creeping feeling I’ve seen this place somewhere before. Little surprise, as I learn the mansion has starred in multiple screen productions across decades, providing a compellingly grand backdrop for the likes of Orson Welles to Taylor Swift.

Later that afternoon, the Northport Hotel’s brilliant white exterior continues inside with tasteful finishings layered by maritime antiquities. My room gives me a twilight-encased view down Main St to the nearby waterfront and Northpoint Bay. That night, I enjoy plump prawns on crushed ice, followed by tender lamb cutlets at the hotel’s restaurant before falling into bed; whether it’s the sensation-laden day or the fresh salty sea air, I don’t know, but I fall asleep effortlessly.

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Autumnal colours are everywhere as I drive north beside the majestic expanse of the Hudson River. I wasn’t expecting so many macabre displays and decorations — even though Halloween is just a few weeks off — as I pull into Sleepy Hollow.

Escape NYC and discover Long Island, the Hudson Valley, and Saratoga Springs’ rich history and stunning landscapes.
Escape NYC and discover Long Island, the Hudson Valley, and Saratoga Springs’ rich history and stunning landscapes.

Although set a century before the Roaring Twenties, the fictional tale of a headless horseman has been attributed to this attractive and pastoral town for over two centuries. I catch a prearranged shuttle bus from the town’s visitor centre to tour one of the grandest properties in the Hudson Valley known as Kykuit, part of the Rockefeller Estate. On the way in, I spot a considerable residence to our right. Our driver confirms this is, in fact, the original family’s games pavilion for their children. A discreet reminder underscoring the obscene wealth of the Gilded Age.

Kykuit, part of the Rockefeller Estate, features a gallery with works by Picasso and Warhol.
Kykuit, part of the Rockefeller Estate, features a gallery with works by Picasso and Warhol.

The following two hours are a dazzling display of sophisticated rooms where the walls, floors, and ceilings seep history and intrigue at every turn. The biggest draw is a sweeping music room, dominated by a gallery-style balcony known as an oculus, allowing those on the floor above to enjoy the grand piano below — without the need to move or potentially spill their martini.

In the basement, we’re steered through an art gallery hosting 20th-century abstract works and modern sculpture. My eyes catch the signature of Picasso, and a Warhol tapestry hangs with little fanfare. I’m impressed to hear the latter once stayed at the estate. But it’s short-lived. Our tour group hears about other notable figures, including past presidents Nixon, Ford, and Reagan, and foreign dignitaries/Nobel prize winners Nelson Mandela and Kofi Annan, who stayed for short periods at Kykuit. If only these walls could talk.

Kykuit, the Rockefeller estate, hosted famous guests, including Nelson Mandela and Andy Warhol. Photo / 123rf
Kykuit, the Rockefeller estate, hosted famous guests, including Nelson Mandela and Andy Warhol. Photo / 123rf

Late afternoon shadows stretch across the leaf-covered streets of Rhinebeck in Dutchess County. Neat redbrick shopfronts housing boutiques and small everyday stores line the main street. Another 100km further north, it’s remarkable to note a more sepia colouration in the trees here.

Although the trip along US Route 9 is an easy-going and scenic affair, traversing this huge state in colonial days would have taken days, and during the Revolutionary Wars it would have been dangerous, too. My stop at the Beekman Arms Inn takes me back to when the founding fathers of modern-day US were on the verge of defying the world’s greatest empire. Inside the oldest running inn in America, it’s gloomy with low-hanging exposed dark wood beams.

The Beekman Arms Inn, the oldest operating inn in the US, hosted George Washington during the Revolutionary War.
The Beekman Arms Inn, the oldest operating inn in the US, hosted George Washington during the Revolutionary War.

It’s said this is often where George Washington and other revolutionary leaders would stay and hold private meetings. I sit at the bar and enjoy a locally brewed pilsner-style beer, taking notice of an empty table with two chairs beside a crackling fireplace. The hairs stand on my neck as I imagine Washington sat beside the flickering light in secret conversations that would ultimately change the course of modern history.

There’s not a single cloud in the sky as I pull into Saratoga Springs the following morning. Famed for its mid-19th century likeness to Las Vegas, this was where the wealthy and elite of New York would come to gamble, watch horse racing, and enjoy fine hotels. Its other well-known attribute is its natural springs, which produce water the indigenous Mohawk people knew had health-giving benefits well before Europeans set foot here.

I head to the Roosevelt Baths & Spa in a sequestered part of the city, surrounded by beautiful parks and tall pine trees, where a private vintage cast iron bathtub with mineral water awaits me. The metallic smell and yellowish appearance are a smidge off-putting, but the soothing, balmy sensation is enough to forget any trepidation once I slip beneath the surface. I’m in heaven for the next half an hour, experiencing the same treatment bon vivants of yesteryear would have had after long nights of drinking and wagering.

Saratoga Springs was once called the Las Vegas of the 19th century for its horse racing and gambling scene. Photo / 123rf
Saratoga Springs was once called the Las Vegas of the 19th century for its horse racing and gambling scene. Photo / 123rf

The next day, I leave without a hurry back towards New York City, joining the Hudson River again and heading south. I’ve heard the Waterfront Farmers Market at Troy, just outside the state capital of Albany, is exceptional. What I’m not expecting, though, is an array of cheery vendors stretching multiple blocks selling all manner of produce and crafts, creating one of the state’s, if not the nation’s, best markets. I drink freshly roasted coffee, pick the ripest apples, and check out endless rails of vintage clothing before realising I must be on the road again.

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I’d be lying if I didn’t admit I wished I had more time to explore New York State outside the city. Maybe I can cancel that hotel booking?

Troy’s Waterfront Farmers Market near Albany is one of the largest and most vibrant in the state.
Troy’s Waterfront Farmers Market near Albany is one of the largest and most vibrant in the state.

Checklist

NEW YORK STATE

GETTING THERE

Fly non-stop from Auckland to John F. Kennedy International Airport with Air NZ and Qantas.

Travel time from the airport to Long Island is approximately 1 hour, 45 minutes by car. Westchester is 1 hour, 30 minutes.

DETAILS

iloveny.com

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