27 Bizarre Vintage Photos From The Annals Of New York City History

Published October 10, 2017
Updated December 6, 2021

These are the little-known yet unforgettable moments that make up New York City history's weird side.

Airship Over Skyline
The German airship Hindenburg, swastikas and all, flies over New York City on the afternoon of May 6, 1937, a few hours before its historic, fiery crash in Manchester Township, New Jersey.AFP/AFP/Getty Images

Waiters On Beam Weird Nyc
Waiters serve lunch to two steel workers on a girder high above the city on November 14, 1930, during construction of the famed Waldorf-Astoria Hotel.Keystone/Getty Images

Statue Of Liberty Head Weird
The as-yet unassembled face of the Statue of Liberty sits unpacked in New York soon after its delivery from France on June 17, 1885.Wikimedia Commons

New York City Bridge Half
The Manhattan Bridge during construction in 1882.Buyenlarge/Getty Images

Horse Fire Engine
A horse-drawn fire engine at 72nd Street and Broadway races toward a fire. Circa 1910.Bettmann/Contributor/Getty Images

Car Grand Central
A car sits on the roof of Grand Central Station following an accident in which a car crashed through the barrier of Park Avenue and ploughed into the roof below, on the corner of 42nd Street and Vanderbilt Avenue. 1944.Weegee (Arthur Fellig)/International Center of Photography/Getty Images

Manhattan Headstand
From a board stuck out from the 54th floor of the Chanin Building, daredevil pole sitter Alvin "Shipwreck" Kelly balances on his head while dunking doughnuts to celebrate Friday the 13. 1939.Bettmann/Getty Images

Carnegie Hill Nyc
Manhattan's Upper East Side. 1882.The New York Historical Society

Philippe Petit Twin Towers
French aerialist Philippe Petit walks a tightrope strung between the tops of the Twin Towers of the World Trade Center. 1974.Alan Welner/AP

La Guardia Throwing Nyc
New York City Mayor Fiorello LaGuardia throws confiscated guns and slot machines overboard into the Long Island Sound. 1937.Ben Sandhaus/NY Daily News Archive/Getty Images

1800s Longacre Square
Longacre Square, not long before it became "Times Square." Circa 1900. Bettmann/Getty Images

Window Washer
A window washer at work on the Empire State Building poses during a brief break from his duties. March 24, 1936.Bettmann/Contributor/Getty Images

Trash Pile Worker New York
A sanitation worker attempts to manage a mountain of garbage, which had accumulated during a citywide garbage strike. 1968.Bettmann/Getty Images

Removing Junk Collyer Weird
Police attempt to enter the residence of the Collyer Brothers, a pair of legendary New York hoarders and recluses, after receiving reports of a foul smell coming from the house. They later found the bodies of the two brothers dead under a mountain of rubbish. 1947.Charles Hoff/NY Daily News via Getty Images

Dry Days Boxes
Workers at a brewery unload thousands of crates of beer, getting ready for the end of Prohibition. April, 1933.Keystone/Getty Images

Hooverville Central Park
During the Great Depression, much of Central Park became a Hooverville, a shanty town named after President Herbert Hoover, who was in office during the market crash and was widely blamed for the Great Depression. 1933. Bettmann/Getty Images

Brennan Farmhouse Nyc
Brennan Farmhouse at 84th Street and Broadway. 1879.The New York Historical Society

Promo Girl Times Square
A woman dressed in only heels and a barrel that reads "I Did My Bit, Did You?" stands in Times Square.

The promotion, organized by the United National Clothing Collection was part of drive to collect clothing and bedding for overseas war relief. April 1945.
Weegee(Arthur Fellig)/International Center of Photography/Getty Images

Plane Crash Weird New York
The scene in the Park Slope neighborhood of Brooklyn after two airplanes crashed to the ground. The planes had collided over foggy New York harbor on December 16, 1960.Paul Bernius/NY Daily News/Getty Images

Times Square Mailbox
New York residents stand outside a giant mailbox stamp-selling booth in Times Square, while the Assistant Postmaster dispenses stamps from inside the booth. 1961.Wikimedia Commons

Tickertape V J Day
People sitting on curb among ticker tape, confetti, and paper after celebrating the end of World War II on V-J Day. August 14, 1945. Alfred Eisenstaedt/The LIFE Picture Collection/Getty Images

Times Square Hats Weird
In July 1921, a crowd reportedly consisting of approximately 10,000 men gather outside the New York Times building in Times Square in order to receive updates on the boxing match between Jack Dempsey and Georges Carpentier.Wikimedia Commons

Streetcar Jump
A streetcar lies motionless just after having jumped the tracks and crashed into a store at the intersection of Nostrand and Putnam Avenues. July 1931.NYC Municipal Archives

Hungover Steps
Revelers recover from New Year's Eve celebrations on the steps of Grand Central Station. Circa 1940.FPG/Hulton Archive/Getty Images

Ebbets Field New York Weird
A Brooklyn youth swings a sledgehammer at the concrete cornerstone of Ebbets Field during an auction sale on the old stomping grounds of the Brooklyn Dodgers. Balls, bats, bases, and other diamond bric-a-brac were sold at the auction. The stadium had recently been torn down to make way for a middle-income housing project. 1960.Bettmann/Getty Images

New York City Weird Stilt Dancing
The New York City ballroom holds a stilt-dancing marathon. Due to the falling of some participants, the Roseland Ballroom owners called a halt to this contest after four hours. February 6, 1922.NY Daily News Archive/Getty Images

Flying By Statue Liberty
Wilbur Wright, of Wright brothers fame, flies a Wright Type A plane by the Statue of Liberty as part of a demonstration. 1909.Wikimedia Commons

From the draft riots of 1863 to the stock market crash of 1929 to the terrorist attacks of September 11, 2001, New York City has played host to many of American history's most notable moments.

But aside from such momentous events, the city has been the site of countless historical episodes that are less well-known yet completely unforgettable — the man who walked a tightrope between the Twin Towers, the brothers who entombed themselves in a maze of trash, and on and on.

Even less well-known still are the tiny little moments that reveal some of the strange little happenings that make New York the unique, ever surprising city that it's always been.

See some of the strangest and most unexpected vintage photos of New York City in the gallery above.


Enjoy these weird pictures of New York City? Next, check out these incredible photos of the undeveloped New York City before it became the modern metropolis we know today. Then, see the terrifying crime and decay of New York in the 1970s.

Gabe Paoletti
Gabe is a New York City-based writer and an Editorial Intern at All That Is Interesting.