We’ve partnered with I LOVE NY, the official New York State Tourism Office, to show you how you can enrich your New York State travel with cultural and historic experiences.
This year marks 100 years since The Great Gatsby was published and has captivated readers with its vivid imagery of Roaring Twenties opulence, ambition and romance. But did you know that F. Scott Fitzgerald’s legendary novel was inspired by real locations across New York State?
From the grandeur of Long Island’s Gold Coast mansions to the historic estates of the Hudson Valley, visitors can immerse themselves in the world of Gatsby while discovering the rich cultural and architectural heritage of the region.
This guide is your key to exploring New York State beyond the buzz of the city, offering a curated list of stunning destinations to experience the state’s glamorous past.
Whether you’re a book lover, a history buff or just looking for a luxurious escape, Upstate New York will transport you to the elegance of the Roaring Twenties and beyond.
Oheka Castle, Huntington (Long Island)
If Gatsby’s infamous parties had a real-world counterpart, they’d be held at Oheka Castle. This French château-style estate, one of the largest private residences in America, is the epitome of Jazz Age luxury. From its sweeping gardens to its grandiose architecture, Oheka is a true masterpiece of the Roaring Twenties.
Just an hour’s drive from NYC, visitors can tour the restored mansion, sip afternoon tea on the terrace, or book an overnight stay in one of its plush guest rooms. It’s the perfect spot to channel your inner Gatsby or Daisy.
Vanderbilt Mansion National Historic Site, Hyde Park (Hudson Valley)
Though built before the Roaring Twenties, the Vanderbilt Mansion exudes the same sense of opulence that defined Gatsby’s world. This Beaux-Arts masterpiece offers a glimpse into the lifestyles of America’s wealthiest families during the Gilded Age, an era that heavily influenced Fitzgerald’s work.
Located 90 minutes from New York City, the estate features formal gardens, stunning Hudson River views, and guided tours that delve into its fascinating history.
Boldt Castle, Heart Island (Thousand Islands)
For romance and extravagance, look no further than Boldt Castle. Built as a love letter to his wife, millionaire George Boldt’s castle boasts grand architecture and lush gardens that rival any Gatsby party setting.
Visitors can take a ferry to the island, explore the castle’s opulent rooms, and enjoy the serene beauty of the surrounding St. Lawrence River. It’s a bit further afield — about a six-hour drive from NYC — but that just makes it the perfect excuse for an Upstate road trip.
Old Westbury Gardens, Old Westbury (Long Island)
A stroll through Old Westbury Gardens feels like stepping into Gatsby’s backyard. This magnificent estate, with its English-style gardens and stately mansion, even served as inspiration for the Buchanan estate in the 2013 Great Gatsby movie.
Visitors can tour the beautifully preserved mansion, explore the sprawling grounds, or attend one of the estate’s many seasonal events. Located just 45 minutes from NYC, it’s an easy day trip for anyone looking to revel in 20th-century grandeur.
Kykuit, The Rockefeller Estate, Sleepy Hollow (Hudson Valley)
Perched atop a hill with breathtaking views of the Hudson River, Kykuit was home to four generations of the Rockefeller family. Its art-filled interiors, lush gardens and storied past provide a captivating window into the grandeur of America’s elite.
Located just an hour from NYC, visitors can explore the mansion, admire its impressive art collection and wander the immaculate grounds.
The Adelphi Hotel, Saratoga Springs (Capital-Saratoga)
Step into this historic hotel, and you’ll feel like you’ve been transported to another era. Recently restored, The Adelphi Hotel combines Victorian elegance with modern luxury, making it a perfect retreat for Gatsby enthusiasts.
After checking in, enjoy a cocktail in the plush bar, dine in the refined restaurant — or simply soak in the glamorous ambiance. Saratoga Springs is approximately three hours from New York City, but its timeless charm makes the trip worth it.
Saratoga Race Course, Saratoga Springs (Capital-Saratoga)
A quintessential Gatsby-esque experience awaits at the Saratoga Race Course. This historic venue captures the thrill and glamour of high society with its elegant grandstands and well-dressed crowds.
Catch a summer race, don your best hat, and enjoy the pageantry of one of the oldest thoroughbred racing tracks in the U.S. It’s an iconic experience that combines history, excitement and style.
Singer Castle, Dark Island (Thousand Islands)
If mystery and charm are more your style, Singer Castle is a must-visit. With its secret passageways and lavish interiors, this early 20th-century gem evokes the intrigue and allure of the Jazz Age.
Accessible only by boat, Singer Castle offers guided tours that showcase its fascinating history and unique architecture. It’s a hidden treasure waiting to be discovered.
From the Gold Coast mansions of Long Island to the timeless estates of the Hudson Valley and beyond, the state offers countless ways to step into Gatsby’s world.
Whether you’re sipping cocktails at Oheka Castle, wandering the grounds of the Vanderbilt Mansion, or watching the horses race at Saratoga, every moment promises an unforgettable blend of sophistication and adventure.
Plan your journey today and discover the timeless allure of New York State — because Gatsby’s dream is closer than you think.