Times Square Trivia
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42 free Times Square trivia questions with answers — geography quiz, new questions added Sep 2026.
Times Square trivia starts with a horse market. This quiz follows the bowtie from Longacre Square and the carriage trade through Adolph Ochs's 1904 tower and subway deal, the first electric ad, the Wrigley sign, the Lincoln Highway's eastern end and Fritz Lang's Metropolis moment. Then it climbs the flagpole on One Times Square for the ball drop: fireworks in 1904, a 700-pound iron ball in 1907, the wartime blackouts, Waterford crystal, an 11,875-pound geodesic sphere, Dick Clark and 3,000 pounds of confetti. The second half covers the zipper's first Hoover headline, the two-million V-J Day crowd and the kiss photograph, the 'sleaziest block in America' years, Midnight Cowboy, Disney and the New Amsterdam Theatre, Bertelsmann and the signage laws, Bloomberg's lawn-chair plazas, the Naked Cowboy's presidential run, the 2010 car bomb, the busiest subway station in the system, and Broadway itself. It should suit anyone who has stood in the crowd, and the harder questions are for New York history buffs. Every answer was checked against Wikipedia's articles on the square, the ball, the tower and the theatres, and the supporting sentence is attached to each question.
30 of 42 questions with answers and explanations. Play the quiz
Q 01Times Square lies in which part of Manhattan?
Midtown
Midtown: the square takes its name from The New York Times, whose new tower there opened in 1904.
Q 02What was Times Square called before 1904, after a London carriage-trade street?
Longacre
Longacre: like London's Long Acre, the neighbourhood was known for the carriage trade, and carriage makers clustered there.
Q 03Which publisher moved The New York Times into the new tower that gave Times Square its name?
Adolph S. Ochs
Adolph S. Ochs: yet the paper outgrew its famous tower within a decade and moved to bigger offices a block away in 1913.
Q 04Which nickname has Times Square long been known by?
The Crossroads of the World
The Crossroads of the World: almost from the start, the square was also where New Yorkers gathered to see in each new year.
Q 05Together with Duffy Square, Times Square is usually likened to which shape?
A bowtie
A bowtie: Broadway slants across Seventh Avenue, leaving two triangles that meet at 45th Street, the northern one being Duffy Square.
Q 06Times Square's northern triangle honours Francis Duffy, who was what in WWI?
An army chaplain
An army chaplain: after serving with New York's 'Fighting 69th', Duffy became pastor of a nearby church, which his statue still faces.
Q 07Which Broadway showman, played on film by James Cagney, has a statue in Duffy Square?
George M. Cohan
George M. Cohan: he wrote 'Over There' when America entered World War I, and Congress later honoured him with a medal for it.
Q 08The TKTS booth, rebuilt in 2008, is topped by red steps that are notable for being made of what?
Load-bearing glass
Load-bearing glass: the booth's new look grew out of a worldwide design competition won by two Australian architects.
Q 09Times Square is the eastern terminus of which pioneering coast-to-coast road?
The Lincoln Highway
The Lincoln Highway, which ran to Lincoln Park in San Francisco, was dreamed up by Carl Fisher, the entrepreneur behind the Indianapolis Motor Speedway.
Q 10Which cigarette brand's famous Times Square billboard showed a man blowing smoke rings?
Camel
Camel: the 'smoke' was really steam, puffed out in rings to look like cigarette smoke.
Q 11Which nickname is given to Broadway's theatre district?
The Great White Way
The Great White Way: the name came from the brilliant electric lights of the district's signs and marquees.
Q 12What did the New York Times' first New Year's Eve party at its tower in 1904 feature, before the ball drop?
Fireworks
Fireworks: but hot ash raining on the crowds worried city officials, fireworks were banned, and from 1907 the Times dropped a ball instead.
Q 13What was the first Times Square ball, dropped in 1907, made of?
Iron and wood
Iron and wood: to promote that first drop, waiters at nearby hotels and restaurants wore light-up top hats spelling out '1908'.
Q 21Frank Sinatra's 1944 shows at which Times Square theatre set off the Columbus Day riot?
The Paramount
The Paramount: tens of thousands of bobby-soxer fans who could not get in swarmed Times Square outside.
Q 22Which company gave its name to the old Times Tower after buying it in the early 1960s?
Allied Chemical
Allied Chemical: it had the tower stripped of its original facade and covered in panels of marble.
Q 23Which toy retailer's Times Square flagship store featured a 60-foot indoor Ferris wheel?
Toys R Us
Toys R Us: the store closed in December 2015, when the chain chose not to renew its lease so as to save on rent.
Q 14The Times Square ball drop was modelled on a 'time ball' atop the building of which company?
Western Union
Western Union: time balls let ship captains check their chronometers, and most were later dismantled.
Q 15Why was the Times Square ball drop called off two years in a row?
Wartime blackouts
Wartime blackouts: the crowd instead marked midnight with a moment of silence, followed by chimes from sound trucks.
Q 16Which manufacturer began supplying the crystal panels on the ball's outer surface in 2000?
Waterford
Waterford: its 'Hope for Healing' panels for the 2001-02 celebration were engraved to honour the victims of the September 11 attacks.
Q 17What shape was the 12-foot Times Square ball introduced for 2008-09?
A geodesic sphere
A geodesic sphere: back in the 1980s an earlier ball had been dressed up as a giant apple for the I Love New York campaign.
Q 18Which host fronted ABC's New Year's Eve countdown from Times Square until his death in 2012?
Dick Clark
Dick Clark: a stroke in late 2004 kept him off that year's show, but he came back on air for the next one.
Q 19What can visitors write on pieces of the confetti dropped over Times Square at midnight on New Year's Eve?
Wishes
Wishes: people write them at a Wishing Wall set up in the square or send them online, and the pieces are mixed into the midnight confetti.
Q 20What nickname did the old Times Tower's moving news sign get?
The zipper
The zipper: the Times switched it on in 1928, years after the paper had moved its newsroom out of the tower.
Q 24An enormous crowd packed Times Square in August 1945 to celebrate what?
Victory over Japan
Victory over Japan: the Times Tower's moving news sign flashed that President Truman had announced Japan's surrender.
Q 25Which magazine published Eisenstaedt's photo of a sailor kissing a woman in Times Square on V-J Day?
Life
He shot it on a Leica IIIa; a 2012 book concluded the woman was dental hygienist Greta Zimmer Friedman, not a nurse.
Q 26Victor Jorgensen's rival Navy photo of the V-J Day kiss is free to use because it is what?
In the public domain
Victor Jorgensen shot the kiss as a Navy photojournalist on duty, so as a US government work his image is in the public domain; it ran in The New York Times the next day.
Q 27Which 1969 film showed the seedy side of Times Square?
Midnight Cowboy
Midnight Cowboy was first released with an X rating, which was later changed to R.
Q 28Which corporation's restoration of the New Amsterdam Theatre kick-started the 1990s clean-up of 42nd Street?
Disney
Disney's mid-1990s restoration of the New Amsterdam Theatre anchored the 42nd Street redevelopment; the city evicted pornographic theatres and brought in Madame Tussauds and AMC, and critics called the result 'Disneyfied'.
Q 29Which musical opened at the restored New Amsterdam Theatre in November 1997?
The Lion King
The Lion King opened at the New Amsterdam on 13 November 1997 and moved to the Minskoff Theatre in 2006 to make way for Mary Poppins; Aladdin opened in the house in 2014.
Q 30From 1913 to 1927 the New Amsterdam Theatre was home to which famous revue?
The Ziegfeld Follies
The Ziegfeld Follies: the first edition, in 1907, proved so popular that Ziegfeld staged a new one almost every year.