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50 free Times Square trivia questions with answers — geography quiz, new questions added Aug 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 50 questions with answers and explanations. Play the quiz
Q 01Times Square lies in which part of Manhattan?
Midtown
Times Square is in Midtown Manhattan, centred where Broadway crosses Seventh Avenue around 42nd Street, a few blocks west of Grand Central Terminal and Bryant Park.
Q 02Before 1904 the plaza was named after a London carriage-trade street. What was it called?
Longacre
Longacre Square took its name from Long Acre in London; William Henry Vanderbilt ran the American Horse Exchange there.
Q 03Which New York Times publisher persuaded the mayor to rename the square and build a subway station in 1904?
Adolph S. Ochs
Adolph S. Ochs, publisher of The New York Times, persuaded Mayor George B. McClellan Jr. to rename Longacre Square as Times Square in April 1904 as the paper moved into its new tower on the old Pabst Hotel site.
Q 04Roughly how many people pass through Times Square on an ordinary day?
330,000
Roughly 330,000 people pass through Times Square on an ordinary day; on the busiest days the count tops 460,000, and the area draws about 50 million visitors a year.
Q 05Times Square is not a square at all; its shape is usually compared to what?
A bowtie
Times Square's shape is usually compared to a bowtie: Broadway's diagonal crossing Seventh Avenue forms two triangles that meet at 45th Street, the northern one officially named Duffy Square.
Q 06Times Square's northern triangle honours Father Francis P. Duffy, who was what in WWI?
An army chaplain
He was chaplain of New York's 'Fighting 69th' regiment; his statue by Charles Keck was dedicated in 1937.
Q 07Which showman, sometimes called 'the man who owned Broadway', has a statue in Duffy Square?
George M. Cohan
George M. Cohan's bronze statue by Georg Lober was unveiled in Duffy Square in 1959; it shares the plaza with the TKTS booth, which has sold same-day discount theatre tickets there since June 1973.
Q 08The TKTS booth, rebuilt in 2008, is topped by red steps that are notable for being made of what?
Load-bearing glass
It was the largest load-bearing glass structure in the world when it opened, with a wedge of bleacher-style stairs for sitting.
Q 09Times Square is the eastern terminus of which pioneering coast-to-coast road?
The Lincoln Highway
The Lincoln Highway, dedicated in 1913 as America's first coast-to-coast road, started at Times Square and ran about 3,389 miles through 13 states to Lincoln Park in San Francisco.
Q 10Which German director said a visit to Times Square inspired his 1927 film Metropolis?
Fritz Lang
Fritz Lang arrived in New York in October 1924 and said the lit-up skyline and Times Square's electric signs shaped the look of Metropolis, released in 1927.
Q 11Which gum brand's early Times Square sign, renting for $9,000 monthly, was called the world's biggest?
Wrigley's Spearmint
The Wrigley's Spearmint sign on Broadway, a block-long electric display of marching spearmen figures, was billed as the largest electric sign in the world and cost about $9,000 a month to rent.
Q 12Why did Broadway's earliest electric signs, source of the 'Great White Way' name, use white lights?
Coloured ones burned out too fast
Early sign makers used white bulbs because coloured ones burned out too fast; the blaze of white light along Broadway earned it the 'Great White Way' nickname by the early 1900s.
Q 13What did the New York Times' first New Year's Eve party at its tower in 1904 feature, before the ball drop?
Q 21One Times Square, the old Times Tower, is how many storeys tall?
25
One Times Square has 25 storeys and rises 363 feet; The New York Times moved out to West 43rd Street in 1913 and sold the building in 1961.
Q 22The 'zipper' news ticker on One Times Square first lit up in November 1928 with a headline about what?
Herbert Hoover's election win
It used 14,800 bulbs driven by a chain conveyor of movable-type letter frames inside the building.
Q 23Which company bought the Times Tower in 1963 and stripped it to its steel frame, cladding it in marble?
Allied Chemical
Allied Chemical bought the tower in 1963 and spent about $10 million stripping it to the steel frame and recladding it in marble as the Allied Chemical Tower, a makeover critic Ada Louise Huxtable deplored.
Fireworks
The 1904 party ended with fireworks fired from the Times Tower; after the city banned fireworks over the crowd, Ochs staged the first ball drop for the 1907-08 celebration instead.
Q 14The first Times Square ball, dropped on 31 December 1907, was lit by how many bulbs?
100
The first ball carried 100 25-watt bulbs on a 700-pound iron-and-wood sphere built by young immigrant metalworker Jacob Starr, whose later firm Artkraft Strauss lowered the ball for most of the century.
Q 15The ball drop was borrowed from a 'time ball' near Trinity Church on the tower of which company?
Western Union
Ochs borrowed the idea from the time ball atop the Western Union Telegraph Building on lower Broadway, dropped at noon daily from 1877 so ships and citizens could set their clocks.
Q 16The ball drop has been skipped only twice, in 1942 and 1943, for what reason?
Wartime blackouts
Crowds instead observed a minute of silence at midnight, followed by chimes played from sound trucks.
Q 17Which manufacturer began supplying the crystal panels on the ball's outer surface in 2000?
Waterford
Waterford Crystal has made the ball's panels since the millennium ball unveiled for 31 December 1999, a six-foot sphere faced with 504 crystal triangles and lit by halogen bulbs.
Q 18The 12-foot Times Square ball introduced for 2008-09 weighed roughly how much?
11,875 pounds
The ball introduced for 2008-09 weighed 11,875 pounds: a 12-foot geodesic sphere of 2,688 Waterford crystal triangles lit by 32,256 LEDs.
Q 19Which host fronted the top-rated Times Square New Year's Eve show until he died in 2012?
Dick Clark
Dick Clark fronted New Year's Rockin' Eve from its 1972 debut until his death in April 2012; after his 2004 stroke he shared hosting with Ryan Seacrest, who then took over.
Q 20How much biodegradable confetti is dropped on the Times Square crowd at midnight each New Year?
3,000 pounds
About 3,000 pounds of confetti, some 1.5 tons of biodegradable tissue paper, is released by hand from rooftops around Times Square at midnight, much of it printed with wishes written by visitors.
Q 24Which financial firm, mocked for paying $27.5 million for One Times Square in 1995, made it a billboard frame?
Lehman Brothers
Lehman Brothers paid $27.5 million in 1995 for a tower too small for offices, let the last tenants leave in 1996 and sold the signage-wrapped building to Jamestown in 1997 for about $110 million.
Q 25Which pharmacy chain leased the entire One Times Square building in 2007 for $4 million a year?
Walgreens
Walgreens leased the whole building in 2007 at about $4 million a year, opened a flagship store there in 2008, and had left by 2022 as a $500 million renovation added an observation deck.
Q 26Times Square's record two-million crowd in August 1945 was celebrating what?
Victory over Japan
The crowd marked Victory over Japan: the zipper flashed 'OFFICIAL *** TRUMAN ANNOUNCES JAPANESE SURRENDER' at 7:03 pm on 14 August 1945 and revellers packed the square into the next day.
Q 27Which 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 28Victor 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 29A 1981 Rolling Stone article called 42nd Street in Times Square what?
The sleaziest block in America
Rolling Stone in 1981 branded 42nd Street 'the sleaziest block in America'; The New York Times had already called it 'the worst block in town' in 1960, when grindhouses and sex shops lined it.
Q 30Which 1969 film's portrait of Times Square as gritty and desperate came to symbolise the area's decline?
Midnight Cowboy
Midnight Cowboy (1969) showed Times Square's hustlers and flophouses through Joe Buck and Ratso Rizzo; Taxi Driver in 1976 doubled down on the same seedy image.