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The Great Gatsby Walking Tour
New York

Follow Nick Carraway through the speakeasies, grand hotels, and ash heaps of Jazz Age New York — the city that made Gatsby possible.

8 stops · All over New York City

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Every Stop Has a Story

Penn Station

The original Penn Station, a pink granite marvel modeled on the Roman Baths of Caracalla, was demolished in 1963 in what's considered one of the greatest architectural crimes in New York history, a loss that led directly to the law that saved Grand Central Terminal.

Grand Central Terminal

Grand Central's Main Concourse ceiling, painted with 2,500 stars to evoke the scale of the universe, sits above the first all-electric rail system in the country, an innovation that let the tracks be buried underground so the surrounding "Terminal City" could rise directly on top of them.

The Yale Club

Completed in 1915 as the largest clubhouse in the world, the Yale Club functioned as a private skyscraper for the Ivy League elite, the same institution where Nick took his regular, oddly gloomy dinners.

The Mansfield

This 1903 "bachelor hotel" for well-to-do single men was the final home of Max Gerlach, a real-life bootlegger who claimed to be a gentleman and famously used the phrase "old sport," a man most scholars agree was the real inspiration for Jay Gatsby.

21 Club

Originally a speakeasy called Jack and Charlie's Puncheon Club, this Prohibition-era hideout hid its liquor behind a disappearing bar that dropped bottles into the sewer at the pull of a lever, the kind of basement bar that likely inspired the ones where Gatsby and Meyer Wolfsheim meet.

The Plaza Hotel

It's inside a suite at this hotel that Nick and the others gather for the sweltering, tumultuous confrontation of Chapter Seven, a French Renaissance château that opened in 1907 and welcomed a Vanderbilt as its very first guest.

Queensboro Bridge

This double-deck cantilever bridge, opened in 1909 as the largest of its kind in the country, transformed Queens from rural farmland into a residential extension of Manhattan, giving Nick the "first wild promise" view of the city that Fitzgerald immortalized in Chapter Four.

Valley of Ashes

Before it became parkland, this site was the Corona Ash Dumps, receiving 100 railroad cars of ash a day and piling into 90-foot mountains of refuse, the grim landscape Fitzgerald turned into the Valley of Ashes.

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