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.
Architecture
Test your mettle with these stony questions centered upon edifices and infrastructure.
1. What is the tallest building in Westchester?
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
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.
A. Cornelius Vanderbilt
B. Jay Gould
C. Jim Fisk
SPORTS
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
Education
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
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)
28. Which of these hip-hop stars never resided in Westchester?
A. DMX
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
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
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
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
42. TRUE OR FALSE
Westchester County has an official song, titled “It’s Westchester for Me”
Answers
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?
