Times Square is one of the most iconic and well-known places in the world. Located in Midtown Manhattan, Times Square is a major commercial intersection and entertainment hub that draws nearly 50 million visitors every year. With its bright lights, towering billboards, and bustling crowds, Times Square has a vibrant energy that makes it a fascinating place to explore.
Riddles are a great way to get your mind working and challenge yourself intellectually. Solving riddles about notable landmarks like Times Square is an entertaining way to learn more about these locations. Below are 75 riddles about Times Square along with their answers to test your knowledge about this famous New York City square.
Riddles About Times Square History
1. I’m named after a prominent newspaper that used to be headquartered where I now stand. What am I?
Answer: Times Square. Times Square is named after The New York Times newspaper, which was previously headquartered at One Times Square.
2. I’m an annual tradition in Times Square where a giant crystal ball descends down a pole at midnight on New Year’s Eve. What am I?
Answer: The New Year’s Eve Ball Drop.
3. I’m the nickname given to the area that is now Times Square back when it used to be known for its seedy reputation. What am I?
Answer: Longacre Square
4. I refer to the theaters found along Broadway near Times Square that historically played musicals and other big entertainment spectacles. What am I?
Answer: The Great White Way
5. I was a mayor known for initiating an urban renewal project that helped clean up Times Square’s unsavory reputation in the 1990s. Who am I?
Answer: Rudy Giuliani
Riddles About Times Square Location
6. I’m the avenue that intersects with Broadway to form the bowtie shape of Times Square. What am I?
Answer: 7th Avenue
7. I’m the long street that runs through Times Square, famous for its theaters and bright lights. What am I?
Answer: Broadway
8. I’m the neighborhood of Manhattan that Times Square is located within. What am I?
Answer: Midtown
9. I’m the body of water located close to Times Square. What am I?
Answer: Hudson River
10. I’m the green space located uptown from Times Square known for its zoo. What am I?
Answer: Central Park
Riddles About Times Square Landmarks
11. I’m the building where the famous New Year’s Eve ball drops every year in Times Square. What am I?
Answer: One Times Square
12. I’m an annual parade filled with giant character balloons that passes through Times Square on Thanksgiving Day. What am I?
Answer: Macy’s Thanksgiving Day Parade
13. I’m the triangular concrete plaza filled with tables and chairs where folks gather in Times Square. What am I?
Answer: Father Duffy Square
14. I’m the headquarters of a major news network located on Broadway in Times Square. What am I?
Answer: Fox News Building
15. I’m a grand old theater that still hosts Broadway shows after over 100 years in Times Square. What am I?
Answer: The Palace Theatre
Riddles About Times Square Signage & Billboards
16. I’m the designer of the big lit-up signs and billboards found all over Times Square. Who am I?
Answer: Douglas Leigh
17. I refer to the giant brightly-lit signs and billboards that are a signature of Times Square. What am I?
Answer: Spectaculars
18. I’m the nickname for the area in Times Square where stock market information used to be displayed on tickers. What am I?
Answer: The Ticker
19. I’m the former newspaper that had a zipper-like news ticker on a building in Times Square. What am I?
Answer: The New York Times
20. I’m the address of the tower where the New Year’s Eve Ball drops each year in Times Square. What number am I?
Answer: One
Riddles About Times Square Culture & Entertainment
21. I’m a glamorous New York theater award named after a theater critic with ties to Times Square. What am I?
Answer: The Tony Award
22. I’m the nickname for the Theater District near Times Square that stages big Broadway shows. What am I?
Answer: The Great White Way
23. I’m the street performer famous for appearing in Times Square as a painted robot. Who am I?
Answer: The Naked Cowboy
24. I’m the annual drop-in event in Times Square each New Year’s Eve where people gather to watch the ball drop. What am I?
Answer: New Year’s Eve in Times Square
25. I’m the glamorous movie premiere that takes place each year in Times Square. What am I?
Answer: The TCM Classic Film Festival
Riddles About Times Square Businesses
26. I’m the globally recognized coffeehouse chain that has a large store right in Times Square. What am I?
Answer: Starbucks
27. I’m the brand of candy with a huge retail store in Times Square filled with M&M’s. What am I?
Answer: M&M’s World
28. I’m the restaurant known for its burgers and shakes that overlooks Times Square from a prime location. What am I?
Answer: Shake Shack
29. I’m the iconic New York restaurant that has a location right in the middle of Times Square’s pedestrian plaza. What am I?
Answer: Red Lobster
30. I’m the global sportswear brand that runs a massive flagship store on Broadway in Times Square. What brand am I?
Answer: Nike
Riddles About Times Square Visitors & Crowds
31. I refer to the annual estimate of how many people pass through Times Square each year. What number am I?
Answer: 50 million
32. I’m the term for when locals avoid Times Square to steer clear of the tourist crowds. What am I?
Answer: Avoiding the Bowtie
33. I’m the nickname for the people who slowly wander through Times Square taking pictures and looking up. Who am I?
Answer: Sidewalk Shufflers
34. I’m the direction people say not to look when walking slowly through Times Square crowds. What direction am I?
Answer: Up
35. I’m the recommended travel tip for efficiently navigating Times Square crowds. What am I?
Answer: Walk faster and with purpose
Riddles About Times Square Safety & Security
36. I’m the city agency responsible for security and law enforcement in Times Square. Who am I?
Answer: The New York Police Department (NYPD)
37. I’m the security measure installed in Times Square to prevent vehicle attacks on pedestrians. What am I?
Answer: Bollards
38. I’m the type of cameras found all over Times Square that help monitor activity there 24/7. What am I?
Answer: Surveillance cameras
39. I’m the counterterrorism squad that has a command center beneath Times Square. What am I?
Answer: NYC Counterterrorism Response Command
40. I’m the annual practice to prepare for New Year’s Eve security in Times Square involving hundreds of officers. What am I?
Answer: New Year’s Eve Security Rehearsal
Riddles About Times Square Economy & Commerce
41. I’m the global credit card company that paid millions for branded signage in Times Square. Who am I?
Answer: American Express
42. I’m the estimated annual economic impact of Times Square on New York City. What dollar amount am I?
Answer: $110 billion
43. I’m the agency that works to attract businesses and tourism to Times Square. Who am I?
Answer: Times Square Alliance
44. I’m the average annual rent for retail space in Times Square per square foot. What dollar amount am I?
Answer: $2,000
45. I’m the Pittsburgh paint supplier who paid for branded content on a Times Square billboard in the 1940s. Who am I?
Answer: Alcoa
Riddles About Times Square Transportation
46. I’m the underground subway system with a major hub at Times Square. What am I?
Answer: The New York Subway
47. I’m the major rail company with a terminal near Times Square. What am I?
Answer: Grand Central Terminal
48. I’m the airline that has a ticketing office located right on Times Square. Who am I?
Answer: American Airlines
49. I’m the NYC bus route that runs right through Times Square What route number am I?
Answer: M42 Bus
50. I’m the bike sharing system that has docking stations located near Times Square. What am I?
Answer: Citi Bike
Riddles About Times Square In Pop Culture
51. I’m the New Year’s Eve-themed romantic comedy film set in Times Square starring Michelle Pfeiffer. What am I?
Answer: New Year’s Eve
52. I’m the Broadway musical set in 1980s Times Square about the goings-on at a seedy burlesque theater. What am I?
Answer: The Producers
53. I’m the movie musical starring Fred Astaire featuring the song-and-dance number “Lullaby of Broadway” set in Times Square. What movie am I?
Answer: 42nd Street
54. I’m the rock musical set in 1970s gritty Times Square featuring hits like “Rent” and “Seasons of Love.” What Broadway show am I?
Answer: Rent
55. I’m the cartoon character that lives in Times Square with his pals in a skyscraper brimming with fun and excitement. Who am I?
Answer: Pete from Mickey Mouse Clubhouse
Riddles About Times Square Events & Traditions
56. I’m the crystallized ball that descends down a pole in Times Square every New Year’s Eve. What am I?
Answer: The New Year’s Eve Ball
57. I’m the person who designed the first version of the dazzling New Year’s Eve Ball. Who am I?
Answer: Walter Palmer
58. I’m the tradition where couples kiss when the ball drops in Times Square on New Year’s Eve. What am I?
Answer: The New Year’s kiss
59. I’m the network that has broadcast the Times Square New Year’s Eve celebrations annually since 1972. What am I?
Answer: Dick Clark’s New Year’s Rockin Eve
60. I’m the annual concert in Times Square where music stars perform to usher in the New Year. What event am I?
Answer: New Year’s Rockin’ Eve
Riddles About Times Square Renovations
61. I’m the NYC mayor who spearheaded major renovations of Times Square in the 1990s. Who am I?
Answer: Rudy Giuliani
62. I’m the architecture firm behind the pedestrian-friendly redesign of Times Square in 2009. Who am I?
Answer: Snøhetta
63. I’m the name of the original transit hub demolished to make way for the new renovated Times Square. What was I called?
Answer: Duffy Square
64. I’m the seating material used in Times Square to discourage lingering when renovating the public plazas. What material am I?
Answer: Granite
65. I’m the overall vision to make Times Square more pedestrian-friendly during major renovations in the 2000s. What was I called?
Answer: Green Light for Midtown
Riddles About Fun Times Square Facts & Firsts
66. I’m the first advertisers to use high-tech billboard lighting effects in Times Square back in the 1920s. Who were we?
Answer: Camel Cigarettes
67. I’m the first woman to get a license to be a Times Square sightseeing guide in 1892. Who am I?
Answer: Annie Moore
68. I’m the motel chain that opened Times Square’s first modern branded storefront in 1959. What chain am I?
Answer: Howard Johnson’s
69. I’m the year that the annual New Year’s Eve ball drop tradition began in Times Square. What year was I?
Answer: 1907
70. I’m the number of lightbulbs used to illuminate the New Year’s Eve Ball in Times Square. What number am I?
Answer: 32,256
Riddles About Times Square Numbers & Statistics
71. I’m the number of annual visitors Times Square receives in millions. What number am I?
Answer: 50 million
72. I’m the number of Broadway theaters located in the Times Square Theater District. What number am I?
Answer: 41
73. I’m the number of streets that intersect at Times Square. What number am I?
Answer: 12
74. I’m the number of subway lines that pass through the Times Square station. What number am I?
Answer: 13
75. I’m the percentage of leased office space found in the Times Square area. What percentage am I?
Answer: 95%
Conclusion
Times Square is such an iconic destination that the riddles about its history, landmarks, events and more are endless! Exploring this famous urban space through unique riddles provides a fun and interactive way to engage with facts and trivia. From its neon lights and New Year’s Eve traditions to its portrayal in pop culture and statistics about visitors, there is a lot to uncover about this vibrant NYC landmark.
The 75 riddles in this article only scratch the surface of the rich stories and details behind Times Square. Its decades of history from the early 1900s to today reveal plenty of fascinating insights. Times Square has evolved from a seedy area known as Longacre Square to the dazzling entertainment hub full of lights and excitement that it is today.
Learning about Times Square through imaginative riddles allows you to connect with its past and present in a more lively, engaging way. Pondering the cryptic clues and guessing the answers draws upon your deduction skills while teaching you new details. Whether you’re a NYC local or an out-of-towner, these Times Square riddles offer an entertaining brain teaser for all.
Next time you’re wandering through the crowds of Times Square, think back to these riddles and discover something new. Look around at the towering billboards, streaming LED displays and selfie-taking visitors to appreciate all the rich history and culture this destination represents. Times Square offers endless intrigue if you take the time to explore its many stories and secrets!
