Long Island plays an essential role in the legacy of “The Great Gatsby,” serving as the real-world backdrop that inspired F. Scott Fitzgerald’s fictional setting.
In particular, the affluent North Shore community of Great Neck—where Fitzgerald and his wife Zelda lived from 1922 to 1924—influenced the creation of West Egg, the novel’s emblematic symbol of new money and ambition.
During the Jazz Age, Great Neck was a vibrant, growing town filled with social climbers, bootleggers and entertainers.
Just across Manhasset Bay, the more established town inspired East Egg, representing inherited wealth and the old social order. Fitzgerald, an outsider among the elite, observed the lavish parties, moral ambiguity and social tensions that came to define the world of Jay Gatsby and his doomed pursuit of Daisy Buchanan.
The author’s brief but formative time in Great Neck shaped the tone and geography of his novel, embedding the identity of Long Island’s Gold Coast into American literary history. Today, local landmarks and the homes along Shore Road offer glimpses into the era that Fitzgerald vividly captured.
A century after its publication in 1925, “The Great Gatsby” remains a cultural touchstone. Readers are still drawn to its themes of love, ambition, identity and the elusive American Dream. The mystery of Gatsby himself, coupled with Fitzgerald’s lyrical prose and social commentary, continues to resonate across generations.
For Long Islanders, the novel is more than a classic—it’s a mirror to the region’s opulent past and an enduring symbol of its place in the American imagination.
Many local libraries, like Great Neck and Syosset, hosted celebrations and book talks in April. If you’re interested in experiencing the opulence of the Jazz Age and the world of F. Scott and Zelda Fitzgerald, this summer, you’re still in luck. The region offers a blend of historic mansion tours, literary events and immersive experiences that transport visitors back to the Roaring Twenties.
Gatsby-Era Mansions to Explore
Long Island’s North Shore, famously known as the Gold Coast, is home to several grand estates that inspired F. Scott Fitzgerald’s “The Great Gatsby.” Here are some notable mansions you can visit:
- Oheka Castle (Huntington): Built in 1914 by financier Otto Hermann Kahn, this 127-room mansion is a prime example of Gilded Age luxury. It served as a backdrop for lavish parties during the 1920s and is believed to have inspired Gatsby’s mansion. Today, Oheka Castle offers guided tours, allowing visitors to explore its historic rooms and gardens.
- Old Westbury Gardens (Old Westbury): This estate features a classic mansion surrounded by formal gardens. It’s open for tours from April through October, providing a glimpse into the lifestyle of the early 20th-century elite.
- Eagle’s Nest at the Vanderbilt Museum (Centerport): Once the summer home of William K. Vanderbilt II, this estate offers public tours on weekends. Visitors can explore the mansion’s living quarters and enjoy panoramic views of Long Island Sound.
Jazz Age Lawn Party–20th Anniversary
Experience the Roaring Twenties at the Jazz Age Lawn Party on Governors Island. Celebrating its 20th anniversary in 2025, this event features live jazz music, vintage fashion and classic cocktails, all set against the backdrop of the island’s historic buildings. The event is scheduled for June 14–15 and August 9–10. Check out www.jazzagelawnparty.com for details.
F. Scott Fitzgerald Society Conference
For literary enthusiasts, the 17th International Fitzgerald Society Conference will be held in New York City from June 22 to 28, 2025. The conference includes a boat tour of Manhasset Bay, offering views of the “East Egg” and “West Egg” areas that inspired the novel. Attendees can also participate in lectures, panel discussions and social events. Visit www.fscottfitzgeraldsociety.org for details.
Great Gatsby Boat Tour
Embark on a Great Gatsby Boat Tour departing from Port Washington with Big Apple Fanatics Tours. This two-hour cruise offers views of the North Shore’s historic estates, providing a unique perspective of the mansions that inspired Fitzgerald’s novel. The next cruise is scheduled for Sunday, May 18. Visit www.bigapplefanaticstours.com for more information.
Mansion Tours and Lectures
- Sands Point Preserve (Sands Point): Explore the Hempstead House and Falaise, two historic mansions open for tours. Falaise is open from late May through November, offering a chance to experience the estate’s preserved interiors.
- Vanderbilt Museum (Centerport): On May 26, 2025, attend a lecture by architect and historian Gary Lawrance titled “Long Island Estates of the Great Gatsby Era.” The lecture will delve into the real-life mansions that inspired Fitzgerald’s novel.
Whether you’re a history buff, literature lover or simply looking to experience the glamour of the Jazz Age, Long Island offers a wealth of opportunities to immerse yourself in the world of “The Great Gatsby.”
