Famous Streets & Squares

22 Times Square Trivia Questions: History, Billboards, and Broadway

Times Square is one of the most famous intersections globally, known for its bright lights, theater district, and massive New Year’s Eve celebration.

This quiz looks at the area’s rich history, including its early horse-trading days and the iconic ball drop. You will see questions about its geography, historic buildings, and famous street performers.

When you finish, you can explore other famous landmarks, learn about global cities of the world, or discover more famous streets and squares.

In which major U.S. city is Times Square located?

Chicago

Chicago

New York City

New York City

Los Angeles

Los Angeles

Las Vegas

Las Vegas

Which famous thoroughfare slices diagonally through Times Square?

Park Avenue

Park Avenue

Broadway

Broadway

Wall Street

Wall Street

Fifth Avenue

Fifth Avenue

What was the name of Times Square before it was renamed in 1904?

Union Square

Union Square

Madison Square

Madison Square

Longacre Square

Longacre Square

Herald Square

Herald Square

Which iconic object is lowered in Times Square to mark the beginning of the New Year?

A silver bell

A silver bell

A giant apple

A giant apple

A crystal ball

A crystal ball

A golden star

A golden star

Approximately how much does the Waterford crystal ball used in the New Year’s Eve celebration weigh?

9,875 pounds

9,875 pounds

12,875 pounds

12,875 pounds

11,875 pounds

11,875 pounds

10,875 pounds

10,875 pounds

In what year did the first New Year’s Eve ball drop take place?

1910

1910

1913

1913

1904

1904

1907

1907

Before it was renamed Times Square, what was the area known as?

Longacre Square

Longacre Square

Herald Square

Herald Square

Madison Square

Madison Square

Union Square

Union Square

Which street performer, known for wearing only briefs, a cowboy hat, and boots, became a fixture of Times Square?

The Times Square Magician

The Times Square Magician

The Subway Performer

The Subway Performer

The Naked Cowboy

The Naked Cowboy

The Broadway Troubadour

The Broadway Troubadour

Which soft drink company has maintained a prominent, multi-story digital billboard in Times Square since the 1930s?

Dr Pepper

Dr Pepper

Coca-Cola

Coca-Cola

Pepsi

Pepsi

7-Up

7-Up

Which numbered street is famously celebrated in a classic musical about the Broadway theater district?

42nd Street

42nd Street

46th Street

46th Street

40th Street

40th Street

44th Street

44th Street

In what year did the City of New York initiate the permanent pedestrianization of the central traffic lanes of Times Square?

2010

2010

2008

2008

2009

2009

2007

2007

Which iconic Alfred Eisenstaedt photograph, taken in Times Square, captures a sailor kissing a nurse to celebrate the end of World War II?

V-E Day

V-E Day

D-Day

D-Day

V-J Day

V-J Day

Armistice Day

Armistice Day

What is the Broadway street address of the building where the New Year’s Eve ball drop ceremony takes place?

1475 Broadway

1475 Broadway

1540 Broadway

1540 Broadway

1560 Broadway

1560 Broadway

1500 Broadway

1500 Broadway

The current New Year’s Eve ball is covered in panels manufactured by which famous glass company?

Steuben Glass

Steuben Glass

Baccarat Crystal

Baccarat Crystal

Waterford Crystal

Waterford Crystal

Swarovski Crystal

Swarovski Crystal

Which historic Beaux-Arts luxury hotel, opened in 1904 in Times Square, was famous for its spectacular roof garden?

The Plaza Hotel

The Plaza Hotel

The Knickerbocker Hotel

The Knickerbocker Hotel

The Pabst Hotel

The Pabst Hotel

The Astor Hotel

The Astor Hotel

For decades prior to its major 2020s redevelopment, what was unique about the status of the building known as One Times Square?

It was used as a government office building

It was used as a government office building

It housed the headquarters of The New York Times

It housed the headquarters of The New York Times

It displayed constant messages for the United Nations

It displayed constant messages for the United Nations

It was mostly vacant and served primarily as a billboard tower

It was mostly vacant and served primarily as a billboard tower

In 2014, a record-breaking digital billboard debuted on the Marriott Marquis in Times Square. Approximately how many square feet did this massive screen span?

45,000 square feet

45,000 square feet

25,000 square feet

25,000 square feet

15,000 square feet

15,000 square feet

35,000 square feet

35,000 square feet

Times Square underwent a massive revitalization project in the 1990s to move away from what reputation?

1970s and 1980s urban decay and crime

1970s and 1980s urban decay and crime

1890s horse carriage trading center

1890s horse carriage trading center

1950s Cold War nuclear drill sites

1950s Cold War nuclear drill sites

1920s Prohibition era speakeasy culture

1920s Prohibition era speakeasy culture

What is the name of the famous red glass staircase booth where tourists purchase discounted same-day Broadway tickets?

The Broadway Ticket kiosk

The Broadway Ticket kiosk

The Lincoln Center box office

The Lincoln Center box office

The Playbill station

The Playbill station

The TKTS booth

The TKTS booth

What is the most common nickname for Times Square?

Red Square

Red Square

The Great White Way

The Great White Way

The Crossroads of the World

The Crossroads of the World

The Canyon of Heroes

The Canyon of Heroes

The first-ever New Year’s Eve ball, created in 1907, was primarily made out of what materials?

Wood and iron

Wood and iron

Plastic and neon gas

Plastic and neon gas

Paper and papier-mâché

Paper and papier-mâché

Steel and lightbulbs

Steel and lightbulbs

Which musical holds the record for the longest-running show in Broadway history?

Wicked

Wicked

The Lion King

The Lion King

Phantom of the Opera

Phantom of the Opera

Chicago

Chicago

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If you liked this, try our architecture trivia, look at other places, or read about art history.

My passion for travel seamlessly integrates with my love for trivia, as I spend a lot of time on the road. I create engaging trivia quizzes based on the information I gather about new locations, food, music, customs, and people.

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