Quiz: How Well Do You Know Westchester County?

Think you’re a Westchester pro? Put your local knowledge to the test to see exactly how well you know the ins and outs of the 914.

By Paul Adler, Nick Brandi & Mackenzie Tatananni

Think you know Westchester inside and out? You may just reconsider after taking this fun yet comprehensive quiz, which tests the wit and wits of intrepid locals with questions ranging from megastar celebs that call the county home to unlikely facts about county sites, institutions, sports, and geography.


Test your mettle with these stony questions centered upon edifices and infrastructure.

1. What is the tallest building in Westchester?

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A. One City Place, White Plains
B. Trump Plaza New Rochelle
C. The Residences at the Ritz-Carlton, Westchester

2. How long is Valhalla’s Kensico Dam?

A. 1,690 feet
B. 1,843 feet
C. 1,917 feet

3. The Union Church of Pocantico Hills boasts stained-glass windows by which acclaimed French artist?

A. Paul Gauguin
B. Pierre-Auguste Renoir
C. Henri Matisse

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4. How skinny is Mamaroneck’s famed Skinny House?

A. 10 feet
B. 14 feet
C. 16 feet

5. In what year was Sleepy Hollow’s iconic lighthouse originally built?

A. 1883
B. 1892
C. 1905

6. This Gilded Age tycoon purchased Lyndhurst mansion in 1880.

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A. Cornelius Vanderbilt
B. Jay Gould
C. Jim Fisk


Calling all sports fanatics — it’s your time to shine. Get out there and show us that you’ve got game!

7. Where in Westchester is the Madison Square Garden Training Facility located?

A. Mount Kisco
B. Tarrytown
C. Yonkers

8. Which of these sports stars has never lived in Westchester?

A. Mariano Rivera
B. Art Monk
C. Derek Jeter

9. The Westchester Flames won the Professional Development League National Championship in this year:

A. 2001
B. 2003
C. 2005

10. The Westchester Knicks are part of this NBA league:

A. The D League
B. The G League
C. The B League

11. Back in the ’80s, where was the NY Giants training camp?

A. Iona College
B. Manhattanville College
C. Pace University

Geography & Stats

Those who think they know every nook and cranny of our county may have cause for pause when they tackle these geography- and municipality-based queries.

12. What is the oldest community in Westchester?

A. Pelham
B. Dobbs Ferry
C. Tarrytown

13. Which of these was once the name of the town of Irvington?

A. King’s Ferry
B. Greenville
C. Dearman

14. Which of these was once the name of Port Chester?

A. New Stratford
B. Bishopville
C. Saw Pit

15. When did the Cross County Center open?

A. 1954
B. 1958
C. 1961

16. Which of these Westchester communities has the smallest population?

A. Buchanan
B. Briarcliff Manor
C. Ardsley

17. What is the highest point in Westchester?

A. Bailey Mountain Peak
B. Titicus Mountain Peak
C. Bald Mountain Peak

18. Which local roadway was the site of the HBO documentary There’s Something Wrong With Aunt Diane?

A. Saw Mill River Parkway
B. Taconic State Parkway
C. Cross County Parkway

19. Per the 2020 Census, what is Westchester’s population?

A. 967,506 people
B. 1,004,457 people
C. 1,104,457 people

20. Including water, how many square miles is Westchester County?

A. 450
B. 500
C. 625


Fancy yourself a Westchester know-it-all? Prove it with this list of questions featuring local high schools, colleges, and universities.

21. Which Westchester-based college is home to the Neuberger Museum of Art?

A. Manhattanville College
B. Purchase College
C. Sarah Lawrence College

The Neuberger Museum of Art
The Neuberger Museum of Art | Photo courtesy of the Tags Group

22. Which of Westchester’s colleges has the largest population of undergrads?

A. Mercy College
B. Westchester Community College
C. Pace University

23. What is the county’s oldest college?

A. Iona College
B. Manhattanville College
C. SUNY Purchase

24. Where did artist Norman Rockwell attend high school?

A. Rye
B. Mamaroneck
C. New Rochelle

25. Which famous politician graduated from Yorktown High School?

A. Alexandria Ocasio-Cortez
B. Nita Lowey
C. George Pataki

26. What boyhood job did New Rochelle’s Don McLean have that he referenced in his anthemic song “American Pie”?

A. Paper Boy
B. Lawn Mowing
C. Lifeguard

Famous Figures

More than a few celebrities have spent time in our cosmopolitan county.

27. What rocker had his mugshot taken by the Yonkers Police Dept?

A. Axl Rose (Guns N’ Roses)
B. Steven Tyler (Aerosmith)
C. Vince Neil (Mötley Crüe)

Concert photo
Adobe Stock | DWP

28. Which of these hip-hop stars never resided in Westchester?

B. Dr. Dre
C. Mary J. Blige

29. Whom did Marilyn Monroe marry at the White Plains Courthouse?

A. Joe DiMaggio
B. Arthur Miller
C. James Dougherty

30. Which of these celebrities was not cremated at Ardsley’s Ferncliff Cemetery?

A. Humphrey Bogart
B. John Lennon
C. Nikola Tesla

31. Which late-night TV host owns a North Salem home?

A. Jay Leno
B. Jimmy Fallon
C. David Letterman

32. Which of these celebs has never called Bedford home?

A. Rob Thomas
B. Glenn Close
C. Scarlett Johansson

33. Which fashion icon owns a stylish county pad in the 914?

A. Michael Kors
B. Ralph Lauren
C. Calvin Klein

34. Name the Westchester town in which former United States Secretary of State Hillary Clinton lives.

A. Chappaqua
B. Scarsdale
C. Bedford

Hillary Clinton. Westchester Quiz
Gage Skidmore | Wikimedia Commons

Fun Facts

Explore a few unlikely corners of Westchester knowledge with these fun and sundry questions.

35. What retail destination has been operating in Westchester the longest?

A. Ridge Hill
B. Cross County Shopping Center
C. The Westchester

Ridge Hill. Westchester Quiz
Ridge Hill | Photo courtesy of Buzzcreators

36. Which Westchester park is home to the Leatherman’s Cave?

A. Ward Pound Ridge Reservation
B. Croton Point Park
C. Rockefeller State Park Preserve

37. Which of these psychedelic rockers never performed at The Capitol Theatre?

A. Grateful Dead
B. The Doors
C. Pink Floyd

Capitol Theatre. Westchester Quiz
Capitol Theatre | Photo by Scott Harris

38. Walter’s Hot Dogs has been serving up the good stuff in the county since?

A. 1916
B. 1919
C. 1921

39. In what Westchester city was the nation’s first elevated mass-transit system built?

A. White Plains
B. New Rochelle
C. Yonkers

40. Which of these hit movies did not film scenes at Rye Playland?

A. Adventures in Babysitting
B. Fatal Attraction
C. Big

41. Which is the wealthiest town in the county (and No. 2 nationwide)?

A. Bronxville
B. Larchmont
C. Scarsdale


Westchester County has an official song, titled “It’s Westchester for Me”



1. C 2. B 3. C 4. A 5. A 6. B 7. B 8. C 9. A 10. B 11. C 12. A 13. C 14. C 15. A 16. A 17. A 18. B 19. B 20. B 21. B 22. B 23. B 24. B 25. A 26. A 2 7. B 28. B 29. B 30. A 31. C 32. C 33. B 34. A 35. B 36. A 37. B 38. B 39. C 40. A 41. C 42. T

If you got:

More than 36 correct: You should consider running for county executive.

26 to 36 correct: You are a bona fide Westchesterite.

15 to 25 correct: We’ll keep you, but you have some homework to do.

Fewer than 15 correct: Either you’re new to the county, or perhaps New Jersey is the place for you.

Related: Quiz: How Well Do You Actually Know Croton-on-Hudson?

Our Westchester Home Design Awards event is June 26!

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Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

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