April 10, 2025 marks the 100th anniversary of the publishing of F. Scott Fitzgerald’s great American novel, The Great Gatsby. Travel back to the Roaring Twenties and immerse yourself in the glitz and glamour of Gatsby’s world in New York—from the Gold Coast mansions of Long Island that inspired the novel’s iconic settings to the Great Gatsby Broadway musical to famous jazz clubs that capture the spirit of the Jazz Age. Photo Credit: @robthomasdrone on Instagram.
Explore the Real-Life Locations Behind The Great Gatsby
Credit: @lyssavec on Instagram
Step into the extravagant world of The Great Gatsby on Long Island’s North Shore, the setting for F. Scott Fitzgerald’s great American novel. Explore the towns of Great Neck and Sands Point, the inspirations for “new money” West Egg and “old money” East Egg, and get on board the Great Gatsby Boat Tour for a two-hour cruise through “courtesy bay” separating the “enormous eggs” where you’ll envision where Gatsby’s mansion might have stood and imagine him gazing at the green light on Daisy’s dock.
Lavish Gold Coast mansions once frequented by society’s elite during the Roaring Twenties now welcome visitors to travel back to an era of opulence. Take guided mansion tours of the Guggenheim estate at Sands Point Preserve (pictured) or book the Gatsby Package for a luxurious stay at OHEKA Castle, a majestic estate on Long Island’s highest point that served as the backdrop for Taylor Swift’s “Blank Space” video. Old Westbury Gardens, the Suffolk County Vanderbilt Museum, Coe Hall in Planting Fields, and Sagamore Hill, site of President Theodore Roosevelt’s summer home, provide even more opportunity to experience the grandeur of the past. Hop on the Long Island Rail Road and head into Manhattan to visit places featured in the book, including Central Park and the Plaza Hotel.
Get Tickets to The Great Gatsby on Broadway
What better way to celebrate 100 years of Gatsby than watching the story come to life on the Broadway stage? See Ryan McCartan as Jay Gatsby and Sarah Hyland as Daisy Buchanan in the Tony Award-winning musical adaptation of the F. Scott Fitzgerald novel, with showings at the Broadway Theatre through September 7. Grab a pre-theater dinner or post-show cocktail at Gatsby’s Landing Times Square. Get even fancier and book The Plaza Hotel’s Gatsby Suite Experience (available through April 30) that includes a minimum two-night stay in the elegant Art Deco-inspired one-bedroom suite brimming with lavish floral arrangements, two tickets to The Great Gatsby Musical on Broadway, and a complimentary drink at The Broadway Theatre.
Party Like Gatsby at Exciting New York Events
Credit: @mkito41 on Instagram
Raise a toast to the 100th anniversary of “The Great Gatsby” during Gatsby Hour in the OHK Bar in Oheka Castle, featuring $15 bar bites, $6 draught beers, $10 wines by the glass, and $12 cocktails (4PM-7PM Monday-Thursday). Don your finest flapper dresses and dapper suits and get ready to party like it’s 1925 at the Jazz Age Lawn Party (pictured), happening June 14-15 and August 9-10 on Governors Island. This glamorous Prohibition Era-inspired gathering features live jazz, a sprawling dance floor where you’ll learn the Charleston and Peabody, gourmet drinking and dining, and more. Step into the jazzy world of the Roaring Twenties as the World Ballet Company brings the glitz, glamor, and tragic romance of F. Scott Fitzgerald’s timeless novel to life with a new Broadway-style ballet. Performances will be held at The Stanley Theatre in Utica on September 20 and The Oncenter – John H. Mulroy Civic Center Theaters in Syracuse on September 21.
Experience All That Jazz at New York Clubs and Festivals
Credit: @sawadamasaharu on Instagram
Embrace the spirit of the Jazz Age with the music that defined the Gatsby era at New York’s jazz clubs and festivals. Feel the rhythm of the 1920s at famed New York City jazz clubs like Blue Note (pictured), Birdland Jazz Club, Smoke Jazz & Supper Club, and Minton’s, the birthplace of bebop. A visit to the Colored Musicians Club Jazz Museum in Buffalo is a must as it is the only remaining African American club of its kind in the United States. Also not to be missed are the Saratoga Jazz Festival (June 29), Rochester International Jazz Festival (June 20-28), Jazz at Lincoln Center performances, and the Art of Jazz series at the Buffalo AKG Art Museum. For a unique experience, learn about the history of jazz with Harlem Heritage Tours and set sail on a jazz cruise aboard a luxury 1920s-style yacht with Classic Harbor Line.
Step Into the Secret World of Speakeasies
The Great Gatsby was set during the Prohibition Era, a time when people defied the law heading to underground speakeasies to enjoy jazz and forbidden cocktails in an atmosphere of decadence and secrecy. In Manhattan, hideaway spots like Please Don’t Tell, The Back Room, and Bathtub Gin echo the secretive allure of the 1920s. In Binghamton, 205 Dry is an authentic 1920s speakeasy hidden behind an old bookcase and in Farmingdale, make sure to give the secret password to get into Charlotte’s Speakeasy hidden in a sweets shop basement. Visit Brotherhood, America’s Oldest Winery, which survived Prohibition by making wine for church services.
Glam It Up at Gilded Age Mansions
Credit: @jahv on Instagram
Transport yourself to the Gilded Age, an era of excess and luxury that spawned the opulent mansions and extravagant parties that filled the pages of The Great Gatsby. The Vanderbilt Mansion in Hyde Park, Staatsburgh State Historic Site, Lyndhurst in Tarrytown (pictured), and Glenview in Yonkers are just some of the stunning examples of grand New York estates that provide a glimpse into the lavish lifestyles of the Gilded Age elite with their expansive grounds, breathtaking views, and elegant architecture.
Live It Up Like Gatsby at New York’s Art Deco Hotels
Credit: @thegiacomohotel on Instagram
Give your getaway the Gatsby treatment by booking a stay at New York’s stunning Art Deco hotels, where elegance and glamour meet modern luxury. Manhattan has no shortage of Art Deco masterpieces including Hotel Edison, JW Marriott Essex House New York, Wyndham New Yorker Hotel, and The Lexington Hotel. Built in 1929, The Giacomo (pictured) in Niagara Falls is a towering achievement of Art Deco architecture within walking distance of Niagara Falls State Park. On Long Island, the Inn at Great Neck, located in the town where F. Scott Fitzgerald once lived, is a luxury boutique hotel replete with Art Deco accents synonymous with the decadent stylings of the 1920s.
Share photos of your New York adventures on Instagram and X (formerly Twitter) with #ILoveNY and #iSpyNY and tag us on Facebook!
