What's now this park was formerly home to "the valley of ashes," where Tom Buchanan's mistress, the ill-fated Myrtle, and her husband Wilson lived near his car-repair shop. It was, at the time, where the Long Island Railroad tracks came up alongside the highway between West Egg and the city, now Northern Boulevard. It was a dump, according to late Fitzgerald expert Matthew J. Bruccoli, who described it in the book's endnotes as a "swamp that was being filled with ashes, garbage, and manure." Flushing was apparently also the home of Fitzgerald acquaintance and used-car salesman Max Gerlach, who probably introduced F. Scott to the expression "old sport" (Gatsby's catchphrase) and who, unfortunately, shot himself in 1939. The parallels to Wilson in profession, area of residence, and personal details are likely not an accident.

Along the Long Island Railroad, the no-man's-land valley of ashes that is now Flushing Meadows-Corona Park (see map point #1) was, according to narrator Nick Carraway, "bounded on one side by a small foul river, and when the drawbridge is up to let barges through, passengers on waiting trains can stare at the dismal scene for as long as half an hour." (We're not sure the bay is any less foul now... ) Imaginary Port Roosevelt, where Wilson stops when he's on a murderous rampage, must have been in Queens, near this bay's Barge Canal Terminal in Queens.

The bridge was the last hurdle for the Long Islanders before they reached their beloved Manhattan, driving their fancy cars at top speed toward the parties and festivities ahead. Crossing it was a significant, empowering moment, as narrator Nick Carraway observes: "Over the great bridge, with the sunlight through the girders making a constant flicker upon the moving cars, with the city rising up across the river in white heaps and sugar lumps all built with a wish out of non-olfactory money. The city seen from Queensboro Bridge is always the city seen for the first time, in its first wild promise of all the mystery and beauty in the world.... 'Anything can happen now that we've slid across this bridge,' I thought. 'Anything at all.'"

When West and East Eggers don't drive, they take the train from Long Island, which deposits them right at the old Penn Station. Nick frequently commutes via this old NYC icon; and Tom Buchanan's mistress, Myrtle Wilson, buys magazines at the newsstand there as well as perfume and cold cream from the station drugstore. Nick, after a long night at a house party with those two, finds himself "lying half asleep in the cold lower level of the Pennsylvania Station, staring at the morning's 'Tribune' and waiting for the four o'clock train." Some things don't change, do they...

At the end of native Midwesterner Nick's sometimes lonely days working in the city as a bond salesman, he retreats to his alma mater's club on Vanderbilt Avenue (where it still is today). It was an unusual respite of scholarly solitude: "I took dinner usually at the Yale Club—for some reason it was the gloomiest event of my day—and then I went upstairs to the library and studied investments and securities for a conscientious hour. There were generally a few rioters around, but they never came into the library, so it was a good place to work."

Nick Carraway's nightly commute progressed from the Yale Club over to Penn, passing this grand Victorian lodging house: "If the night was mellow, I strolled down Madison Avenue past the old Murray Hill Hotel and over Thirty-Third Street to the Pennsylvania Station."

The National Biscuit Company, now called Nabisco, had several cookie-making plants and factories in West Chelsea (in particular, where Chelsea Market is now). During one of Carraway's hot summertime commutes between West Egg and Penn Station, which apparently, in his world, passed through Chelsea, "[o]nly the hot whistles of the National Biscuit Company broke the simmering hush at noon."

A hotel on 43rd Street and Broadway (apparently the first to be entirely kitted out with running water in every room) that was home to a notorious murder. Gatsby and Meyer Wolfsheim wax nostalgic about their old hangout ("filled with faces dead and gone... filled with friends gone now forever"), even though it was built in 1912, only 10 years before the novel is set. (The occurrence of World War I in the interim undoubtedly changed the vibe for regulars.) It is nearby, in an unnamed "well-fanned Forty-second Street cellar," where Gatsby and Nick have lunch and run into Wolfsheim. Wolfsheim and Gatsby also met for the first time on 43rd Street, at the fictional Winebrenner's poolroom, when Gatsby was poor and just out of the army.

This is where Florenz Ziegfeld's show full of showgirls, "Follies," was performed in the 1920s. Starlet Gilda Gray's understudy was a much-buzzed about attendee at one of Gatsby's West Egg soirees. In fact, lots of "theatrical people" came to Gatsby's beachfront ragers.

In search of a place to go to escape the summer heat, Jordan Baker suggest the big cinemas around 50th Street. Midtown then, as now, was almost gloriously stifling that time of year. "I love New York on summer afternoons when everyone's away," Baker comments. "There's something very sensuous about it—overripe, as if all sorts of funny fruits were going to fall into your hands."

The iconic hotel is where Nick Carraway has tea with Jordan Baker, and, later, where the whole gang gathers on a hot summer day in the parlor of a suite for some raucous arguments between Gatsby and Tom Buchanan over Daisy that precede a sad accident on the way home to Long Island. It turned out that their attempt to beat the heat merely resulted in more heat: "The notion originated with Daisy's suggestion that we hire five bathrooms and take cold baths, and then assumed more tangible form as 'a place to have a mint julep.'... The room was large and stifling, and, though it was already four o'clock, opening the windows only admitted a gust of hot shrubbery from the Park."

Nick Carraway and on-again/off-again flame golf pro Jordan Baker go on a romantic evening drive "in a Victoria" (an old-school car, one presumes). It was an ideal setting for some flirtin': "The sun had gone down behind the tall apartments of the movie stars in the West Fifties and the clear voices of little girls, already gathered like crickets on the grass, rose through the hot twilight... It was dark now and as we dipped under a little bridge I put my arm around Jordan's golden shoulder and drew her to me... We passed a barrier of dark trees, and then the facade of Fifty-ninth Street, a block of delicate pale light, beamed down into the Park."

This part of Washington Heights is where Myrtle Wilson's urban pied-a-terre is located, on the top floor "a long white cake of apartment houses." It was decorated with oversized tapestried furniture, and in it narrator Nick, Myrtle, her sister, Tom Buchanan, and the McKees (neighbors) get wildly drunk in the middle of the afternoon, all while the apartment remained "full of cheerful sun" till 8 p.m. Welcome to New York, Nick.

Nick Carraway works (somewhat uneasily, it seems) at the made-up Probity Trust company down in the FiDi, amid what he calls "the white chasms of lower New York." He lunches with the clerks and other young bond salesman "in dark crowded restaurants on little pig sausages and mashed potatoes and coffee." (Photo: the Financial District in 1922, the year the novel is set.)

When Nick tells Gatsby that his extravagant mansion looks like a World's Fair, Gatsby suggests that they just hop in the car and go to Coney Island. In many renditions of the novel's cover, including the original pictured, the hazy face of a woman (probably Daisy) is superimposed over some nondescript glowing neon lights. Those lights are roughly taken from or inspired by the Coney Island skyline, according to late Fitzgerald expert Matthew J. Bruccoli.