Our Ultimate Westchester County Quiz

So, Westchester, you think you’re pretty smart, huh? Sure, you probably know a bunch of state capitals and at one point understood photosynthesis. But how much do you know about your own home county? Well it’s time to find out. We here at Westchester Magazine are saturated with county factoids, tidbits, lore, and gossip all day, every day, and we’ve taken some of the most surprising, exciting, and, frankly, obscure facts that we’ve ever seen and put them in this quiz. We’re talking “Daily Doubles on the Jeopardy! Tournament of Champions” hard. Think you know the answers? There’s only one way to find out… Let’s get quizzical!

(Answer key on page 2)

by the numbers

1. Approximately how many people board Metro-North in Westchester bound for the City on an average weekday?
a) 750
b) 7,500
c) 75,000
d) 750,000

- Advertisement -

2. Approximately how much of our energy does Indian Point provide?
a) 15%
b) 20%
c) 25%
d) 30%

3. Where does Westchester’s population rank among the counties of New York State?
a) Fifth most populous
b) Sixth most populous
c) Seventh most populous
d) Eighth most populous


this land is our land

4. In what year was Westchester County created by an act of the New York General Assembly?
a) 1643
b) 1664
c) 1683
d) 1777

5. In 1775, how did Westchester relate to other counties in the New York colony?
a) It was the largest.
b) It was the richest.
c) It was the most populous.
d) Both b and c

- Partner Content -

6.Which of the following Bronx neighborhoods was originally part of Westchester?
a) Kingsbridge, named for the bridge erected there by Frederick Philipse, who owned land up to Croton
b) Pelham Bay, which was once part of the land extending all the way to Rye that Thomas Pell purchased in 1654
c) Eastchester, which was once part of the Westchester town of the same name
d) All of the above


life & liberty

7. John Peter Zenger’s 1735 trial for seditious libel, which occurred as a result of his writings about an election held in Eastchester, helped enshrine freedom of the press in the Bill of Rights. What other treasured American liberty has connections to that election?
a) Freedom of religion: The Eastchester sheriff attempted to disenfranchise Quakers, who were mostly voting against his preferred candidate, by making them affirm their vote with an oath on the Bible, which was against their religion. A law was soon passed making such affirmations illegal.
b) The right to bear arms: To protect a Crown-granted colony monopoly on the lucrative hunting of beavers for their furs, the governor limited the rights of people living in towns to own guns. The new councilman gave the opposition enough votes to repeal the law.
c) The right to a speedy and public trial: In order to prevent the election’s winner from becoming chief justice, the governor charged him with sedition but delayed the trial to take advantage of a law forbidding the seating of justices under indictment. Only when, two years later, the king intervened, citing the Magna Carta, was the affair resolved.
d) Freedom from excessive bail: In order to prevent the winner from becoming a councilman, the governor charged him with trespassing on the land of one of his tenant farmers and imposed exorbitant bail to take advantage of a law forbidding the seating of anyone in debt servitude as a public official. Only when, two years later, the king demanded the bail be reduced to two pounds was the affair resolved.

8. When British Army Major John André was captured in civilian clothes outside Tarrytown on September 23, 1780, where was he carrying the plans for the fort at West Point that Benedict Arnold had provided him?
a) In his shoes
b) In his coin purse
c) In his tri-corner hat
d) In his horse’s feed bag

9. Long before Hillary Rodham Clinton landed in Chappaqua, another secretary of state called Westchester home. David Dean Rusk, who served from 1961 to 1969 under JFK and Lyndon Johnson, even returned to receive his former township’s Man of the Year Award in 1967. The denizens of the community reacted in silent protest to Rusk’s defense of American involvement in the Vietnam War. Which of the following town’s citizens kept mum?
a) Scarsdale
b) Bronxville
c) Larchmont
d) Rye

- Advertisement -

10. In 1985, the US Supreme Court left intact a federal appeals court decision that dismissed the Scarsdale government’s ability to ban a nativity display in a public park (ACLU v. Scarsdale, New York)—as long as the crèche was balanced out with secular symbols. This stipulation became known as:
a) The Evergreen Act
b) The Snowman Statute
c) The Reindeer Rule
d) The Canon Clause


sites & such

11. Most proud Westchesterites know that the Bronx River Parkway was the country’s first parkway and a crucial innovation to the development of the suburbs. But in what order were the first sections of our other three waterway-named parkways completed?
a) Sprain, Saw Mill, Hutch
b) Hutch, Sprain, Saw Mill
c) Saw Mill, Sprain, Hutch
d) Saw Mill, Hutch, Sprain

12. Which New York City landmark does not incorporate marble from the famed Tuckahoe quarries?
a) The New York Public Library’s main branch
b) St. Patrick’s Cathedral
c) Washington Square Arch
d) Woolworth Building

13. Which of our famous cemeteries made it onto a Lonely Planet list of the top 10 cemeteries in the world along with the Taj Mahal, the Pyramids of Giza, and the Catacombs of Rome?
a) Sleepy Hollow Cemetery, where Washington Irving, Andrew Carnegie, and numerous Rockefellers are buried
b) Ferncliff Cemetery, where James Baldwin, Yul Brynner, Joan Crawford, Judy Garland, Jim Henson, Thelonious Monk, Malcolm X, and Ed Sullivan are buried
c) The Kensico Cemetery, where Anne Bancroft, Lou Gehrig, Beverly Sills, and Ayn Rand are buried
d) Hartsdale Pet Cemetery & Crematory


most infamous

14. Which of the following Westchester areas is held in local legend to be a location of some of Captain Kidd’s buried treasure?
a) Huckleberry Island off New Rochelle
b) Chicken Island in Yonkers
c) Hen Island off Mamaroneck
d) Richards Island off Dobbs Ferry

15. Which criminal “celebrity” was never imprisoned at Sing Sing?
a) Gangster Bugsy Siegel
b) Soviet spy Julius Rosenberg
c) Bank robber Willie Sutton
d) Serial killer Albert Fish

16. What minor infraction led police to arrest Yonkers resident David Berkowitz as the Son of Sam serial killer?
a) A littering violation
b) Turnstyle jumping
c) A parking ticket
d) A bounced check
penned in

17. Which musical takes place in New Rochelle—and was based on a novel also written there?
a) Rent
b) Ragtime
c) Hello, Dolly!
d) Damn Yankees

18. Which well-loved American poem was written in Westchester?
a) “The Red Wheelbarrow,” William Carlos Williams
b) “The Road Not Taken,” Robert Frost
c) “Trees,” Joyce Kilmer
d) “Paul Revere’s Ride,” Henry Wadsworth Longfellow

19. Pound Ridge, the 5,000-person community the New York Times has called “affluent, rural, and very, very private,” has served as a haven for celebs including Richard Gere, Christopher Reeve, Susan Sarandon, Tim Robbins, and Tom Brokaw, not to mention Hume Cronyn and Jessica Tandy. But which musically gifted, long-time resident honored the town in song?
a) Recording star turned Catwoman Eartha Kitt
b) Broadway producer Robert Whitehead
c) King of Swing Benny Goodman
d) Multiple Tony Award-winner (and Mrs. Robert Whitehead) Zoe Caldwell


on screen

20. Rob Petrie of the popular 1960s sitcom The Dick Van Dyke Show lived in New Rochelle at 148 Bonnie Meadow Road and was based on series creator Carl Reiner, who actually lived where in the Queen City?
a) 148 Bonnie Meadow Drive
b) 48 Bonnie Meadow Road
c) 148 Sunny Meadow Road
d) 148 Scarsdale Boulevard

21. Which of the following is one of Westchester’s many appearances in a based-on-real-events movie?
a) Ardsley, as the childhood town of Beverly Donofrio (Drew Barrymore) in Riding in Cars with Boys       
b) A Purchase mansion as the house where John Nash (Russell Crowe) deposits what he believes to be decoded Soviet messages in A Beautiful Mind          
c) Sarah Lawrence as the Harvard campus in The Social Network
d) A Yonkers soundstage as the location of many sets in American Gangster

22. Titanic beauty Kate Winslet originally hails from Reading, England, but the Oscar-winning actress has starred in more than one work with ties to Westchester. Which of the following does not?  
a) Eternal Sunshine of the Spotless Mind
b) Mildred Pierce (miniseries)
c) Revolutionary Road
d) Little Children

23. Boy meets girl. Boy and girl fall in love, get married, pop out 2.5 kids…and move to the ’burbs. At least that’s how it goes on our favorite sitcoms. Which of these beloved television shows employed the old moving-to-Westchester plot?
a) I Love Lucy
b) How I Met Your Mother
c) Friends
d) Both b and c


team spirit

24. What breed of dog is Pace University’s mascot, T-Bone?
a) Scottish Terrier
b) Irish Setter
c) English Bulldog
d) Cavalier King Charles Spaniel

25. What do Iron Man 2, 127 Hours, The Girl with the Dragon Tattoo, and The Social Network have in common? They each star Kate or Rooney Mara, the football-dynasty-heiresses-cum-Hollywood-darlings from Bedford. To which of these sporting enterprises besides the New York Giants (there are at least two) does the Mara family have connections?
a) Pittsburgh Pirates
b) Empire City at Yonkers Raceway
c) Madison Square Garden
d) Pittsburgh Steelers

26. We all remember decathlon gold medalist (and current step-patriarch to the Kardashian klan) Bruce Jenner, a Mount Kisco native who shot to Olympic stardom at the 1976 Montreal Olympics. Hudson Valley athletes competed in all but which of the following events during this summer’s games in London?    
a) Field hockey
b) Gymnastics
c) Mountain cycling
d) Equestrian show-jumping

27. Speaking of Olympians, remember 2008’s men’s tennis upset featuring hard-charging American James Blake? Blake just missed the podium in Beijing after beating World No. 1 Roger Federer for the first time in his career. At least he has brains to fall back on—he attended Harvard after graduating Fairfield Prep. But he was born right here in:
a) New Rochelle
b) Yonkers
c) Mount Vernon
d) Mamaroneck


martians and dragons and bones…oh my!

28. Once upon a time, there weren’t any roads to flood, repair, or complain about in these parts (or elsewhere), and the native beasts roamed free. Nowadays, infrastructure’s improved, but many of our wildest things have moved on…to that greener pasture in the sky. Which of these now-extinct beings can still be found here in relic form?
a) Aurochs, a large type of cattle
b) Mastodon, elephant/mammoth look-alike
c) Quagga, half zebra, half horse
d) Irish Elk, aka “giant deer”

29. Bright lights, big…UFO? Rumors of extraterrestrial activity swirled through the county in August 1995 when locals observed an otherworldly glow emanating from Playland. The luminescence was actually caused by industrial-sized lights brought in for the production of a major pop diva’s music video. Which ’90s songstress, who can be seen rollerblading down the boardwalk and riding the Dragon Coaster in the video’s final cut, was it?
a) Britney Spears
b) Mary J. Blige
c) Mariah Carey
d) Beyoncé

30. Time to look up. Last year we told you about Westchester’s sister city (yes, city), Jingzhou, China. In 1998, Jingzhou gifted us the Chinese Friendship Pavilion, located in Somers’s Lasdon Park, Arboretum and Veterans Memorial, with its blue and gold dragons among the clouds of the interior ceiling and on the structure’s exterior overhang. The mythical creatures represent the people of Westchester and Jingzhou. So, how many dragons are there?
a) 18
b) 80
c) 108
d) 180


what’s in a name?

31. As plenty of exasperated parents can attest, you don’t always get to pick your own—or your kid’s—nickname. (For the record, in lieu of Westchester, we prefer “Golden Apple” to the less-accurate “upstate.”) Match these towns to the other monikers they’ve been called: Tarrytown, Somers, Yonkers, Pound Ridge.  
a) Basket Town
b) Cradle of the American Circus
c) Millionaires’ Colony
d) City of Gracious Living

32. Before Dobbs Ferry became home to William Dobbs’ ferry line in 1730, what was the town known as?
a) Wysquaqua
b) Nepperhan
c) Rananchqua
d) Apawamis

33. A lighthouse just off New Rochelle in Long Island Sound goes by what macabre name?
a) The Black Coffin Flame
b) Ghost Landing Lighthouse
c) Execution Rocks Light
d) Drowning Man Point

Click to page 2 for the answers



by the numbers
1. c) 75,000
2. d) 30%
3. c) Seventh most populous—behind Kings County, i.e., Brooklyn; Queens County; New York County, i.e., Manhattan; Suffolk County; Bronx County; and Nassau County

this land is our land
4. c) 1683
5. d) Both b and c
6. d) All of the above—all of the Bronx was part of Westchester until it was annexed to the City in various stages during the 19th century.

life & liberty
7. a) Freedom of religion: The Eastchester sheriff attempted to disenfranchise Quakers, who were mostly voting against his preferred candidate, by making them affirm their vote with an oath on the Bible, which was against their religion. A law was soon passed making such affirmations illegal.
8. a) In his shoes
9. a) Scarsdale—Rusk, originally from Georgia, lived on Fenimore Road and was president of the Rockefeller Foundation from 1952 to 1960 before John F. Kennedy nominated him to be secretary.
10. c) The Reindeer Rule

sites & such
11. d) Saw Mill, Hutch, Sprain—although construction of the first part of the Hutch began before that of the Saw Mill.
12. d) Woolworth Building
13. d) Hartsdale Pet Cemetery & Crematory

most infamous
14. a) Huckleberry Island off New Rochelle
15. a) Gangster Bugsy Siegel
16. c) A parking ticket

penned in
17. b) Ragtime
18. c) “Trees,” Joyce Kilmer—in Larchmont
19. c) King of Swing Benny Goodman—Benjamin David “Benny” Goodman wrote the song “Pound Ridge” as an homage to the up-and-coming enclave for writers and artists, where he had a home in the 1940s.

on screen
20. b) 48 Bonnie Meadow Road
21. d) A Yonkers soundstage as the location of many sets in American Gangster
22. d) Little Children—Yonkers and Mount Vernon provide the backdrop in several Spotless scenes; parts of Pierce were filmed in Peekskill; the film version of Revolutionary Road is based on the namesake novel by Richard Yates, who grew up in Ossining near the real Revolutionary Road.
23. d) Both b and c—Mother’s Ted buys a house here in hopes of speeding along the settling-down process, despite not yet having found “the one” to share it with; in “The One Where Chandler Gets Caught,” Chandler and Monica break the news to the rest of the Friends gang that they’re leaving their City digs.

team spirit!
24. b) Irish Setter—the team is the “Pace Setters.”
25. b) Empire City at Yonkers Raceway—Kate and Rooney’s maternal grandfather, Tim Rooney, has owned and operated the Yonkers Raceway Corporation since 1972; d) Pittsburgh Steelers—the sisters’ great-grandfather, Art Rooney, Sr., founded the NFL team, originally dubbed the “Pittsburgh Pirates.” Their great-uncle, Dan Rooney, is chairman of the organization, as well as the US Ambassador to Ireland.
26. b) Gymnastics—Women’s field hockey defender Melissa Gonzalez’s hometown is Mohegan Lake; Kingston-born mountain cyclist Todd Wells finished tenth in the men’s cross-country final; Reed Kessler from Armonk and McLain Ward of Brewster, New York, both competed in team show-jumping for the US, which finished in sixth place.
27. b) Yonkers

martians and dragons and bones…oh my!
28. b) Mastodon, elephant/mammoth look-alike—Visit the Trailside Nature Museum at Ward Pound Ridge Reservation to view the remains of our very own mastodon, which, with its shaggy hair and long tusks, would have stood 7 to 9 feet tall and measured 10 to 14 feet in length. North American species of the mammal, which were hunted by early humans during the Ice Age, died out about 10,000 years ago for unknown reasons.
29. c) Mariah Carey—Carey’s directorial debut, “Fantasy,” was released on September 12, 1995.
30. c) 108

what’s in a name?
31. a) Pound Ridge b) Somers c) Tarrytown  d) Yonkers
32. a) Wysquaqua
33. c) Execution Rocks Light

Our Best of Westchester Party is July 24!

Our Westchester Home Design Awards event is June 26!

Our Wine & Food Festival returns June 4-9!

Our Wunderkinds event takes place on May 23!

Our Best of Business Ballot is open through May 15!

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!

Holiday flash sale ... subscribe and save 50%

Limited time offer. New subscribers only.