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
It is formed where Broadway crosses Seventh Avenue at 42nd Street; that diagonal cutting across the 1811 grid gives the plaza its bowtie shape.
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
The paper's new tower stood on the site of the short-lived Pabst Hotel; the first electrified ad appeared on a nearby bank three weeks later.
Q 04Roughly how many people pass through Times Square on an ordinary day?
330,000
On the busiest days it tops 460,000, and the square draws an estimated 50 million visitors a year.
Q 05Times Square is not a square at all; its shape is usually compared to what?
A bowtie
Two triangles meet at 45th Street; the northern one is officially 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
He shares the space 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
Chosen in 1913, the road ran 3,389 miles through 13 states to Lincoln Park in San Francisco.
Q 10Which German director drew inspiration for his 1927 film Metropolis after seeing Times Square in 1923?
Fritz Lang
Critics G. K. Chesterton and Thorstein Veblen were less impressed by the advertising.
Q 11Which 1920s Times Square chewing-gum sign, renting for $9,000 a month, was called the world's biggest?
Wrigley's Spearmint
Advertising spend in the square more than tripled over that decade.
Q 12Broadway's 'Great White Way' nickname arose because early electric signs used white lights. Why?
Coloured ones burned out too fast
The Red Mill was the first show to install electric signs outside its theatre.
Q 13What did the New York Times' first New Year's Eve party at its tower in 1904 feature, before the ball drop?
Fireworks
Q 21One Times Square, the old Times Tower, is how many storeys tall?
25
It rises 363 feet; the newspaper only stayed until 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
The $10 million makeover came a year before the city's Landmarks Preservation Commission gained real power, to critic Ada Louise Huxtable's dismay.
The city banned launching them over the crowd, so Ochs wanted a bigger, safer spectacle for 1907.
Q 14The first Times Square ball, dropped on 31 December 1907, was lit by how many bulbs?
100
It weighed 700 pounds and was built by sign company Artkraft Strauss under Ukrainian metalworker Jacob Starr.
Q 15The ball drop was borrowed from a 'time ball' near Trinity Church on the tower of which company?
Western Union
Time balls were dropped at set hours 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
By the mid-2020s the ball carried more than 5,000 circular panels inscribed with a yearly theme.
Q 18The sixth Times Square ball, introduced for 2008-09, was 12 feet across and weighed roughly how much?
11,875 pounds
It was an icosahedral geodesic sphere lit by over 32,000 LEDs; a 12.5-foot seventh ball debuted for 2025-26.
Q 19Which host fronted the top-rated Times Square New Year's Eve show until he died in 2012?
Dick Clark
Ryan Seacrest took over New Year's Rockin' Eve after him; Guy Lombardo's CBS special was the earlier rival.
Q 20How much biodegradable confetti is dropped on the Times Square crowd at midnight each New Year?
3,000 pounds
The tradition dates from 1992; sanitation crews cleared over 50 tons of rubbish after the 2014 celebration.
Q 24Which financial firm, mocked for paying $27.5 million for One Times Square in 1995, made it a billboard frame?
Lehman Brothers
The tower was too small to make sense as offices; the last office tenants left in 1996 and Jamestown has owned it since 1997.
Q 25Which pharmacy chain leased the entire One Times Square building in 2007 for $4 million a year?
Walgreens
Its flagship opened in 2008 and had closed by 2022 as a $500 million renovation added an observation deck.
Q 26Times Square's record two-million crowd on 15 August 1945 was celebrating what?
Victory over Japan
The zipper announced it with the headline 'OFFICIAL *** TRUMAN ANNOUNCES JAPANESE SURRENDER'.
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
Made by a federal employee on duty, it cannot be copyrighted; his version pins the spot outside the Chemical Bank building.
Q 29A 1981 Rolling Stone article called 42nd Street in Times Square what?
The sleaziest block in America
By 1984 the whole area paid the city just $6 million in property taxes; The New York Times had called it the worst block in town as early as 1960.
Q 30Which 1969 film's portrait of Times Square as gritty and desperate came to symbolise the area's decline?
Midnight Cowboy
Taxi Driver in 1976 doubled down on the same seedy image.