60 free New Haven trivia questions with answers — geography quiz, new questions added Aug 2026.
New Haven, Connecticut punches far above its size in trivia. It was America's first planned city, laid out as nine squares around a Green in 1638. It claims the first hamburger, the first lollipop, the first telephone exchange, the Erector Set and the Frisbee. And it is the home of coal-fired apizza, white clam pies and a burger joint that will throw you out for asking for ketchup. This quiz covers the whole city, not just Yale. You'll get questions on the Puritan founders and the regicides hiding on West Rock, the Amistad trial, Eli Whitney and the arms makers, Wooster Square's cherry blossoms, East Rock, the Shubert Theatre's Broadway tryouts, the Yale Bowl, Toad's Place, and the presidents and inventors who passed through town. Questions range from easy to expert, so locals, Yalies and visitors who only know the pizza can all play. Every answer was checked against Wikipedia and related reference pages, and each question shows the sentence that backs it up.
30 of 60 questions with answers and explanations. Play the quiz
Q 01New Haven sits on the northern shore of which body of water?
Long Island Sound
The city is drained by three rivers, and its large, shallow harbor is an embayment of the Sound.
Q 02New Haven's nickname, 'The Elm City', traces back to what civic innovation?
The first public tree-planting program in the US
Most of the original elms died of Dutch elm disease in the mid-20th century, and disease-resistant elms were replanted from the 1980s.
Q 03New Haven's original 1638 street layout is known by what name?
The Nine Square Plan
The American Planning Association recognizes it as a National Planning Landmark, and the central open square became the New Haven Green.
Q 04Roughly how large is the New Haven Green?
16 acres
Legend says the Puritans sized it to hold the 144,000 people they believed would be spared at the Second Coming.
Q 05Which Native American people lived around New Haven Harbor before the English arrived?
The Quinnipiac
Under attack from neighboring Pequots, they sold their land to the settlers in exchange for a pledge of protection; the town was briefly called Quinnipiac before being renamed.
Q 06Which two men led the 500 Puritans who founded New Haven in April 1638?
John Davenport and Theophilus Eaton
They wanted a stricter theocracy than Massachusetts allowed; the New Haven Colony forbade other churches entirely.
Q 07What happened to the 'Great Shippe' New Haven sent fully loaded to England in 1646?
It vanished and was never seen again
The loss set New Haven back badly against rising rivals Boston and New Amsterdam.
Q 08What is the West Rock formation where two of Charles I's regicides hid in 1661 called?
Judges' Cave
Edward Whalley and William Goffe were later joined by a third regicide, John Dixwell; the trail to the cave on West Rock is the Regicides Trail.
Q 09New Haven shared the role of Connecticut's capital with Hartford from 1701 until which year?
1873
The last state house on the Green, an 1831 Greek Revival building by Ithiel Town, was demolished in 1889 despite preservationist protests.
Q 10Yale moved to New Haven in 1716 from which Connecticut town?
Old Saybrook
It was still called the Collegiate School; the Yale name came two years later after a donation from East India Company merchant Elihu Yale.
Q 11Elihu Yale, whose 1718 gift renamed the Collegiate School, made his fortune as governor of which outpost?
Madras
He donated nine bales of goods that sold for more than £560, and Cotton Mather suggested the college take his name.
Q 12Which future traitor led New Haven's Governor's Foot Guard to seize the powder house on April 23, 1775?
Benedict Arnold
They armed themselves for a three-day march to Cambridge; the city re-enacts it every April on the Green.
Q 13Who became New Haven's first mayor when it was incorporated as a city in 1784?
Roger Sherman
Sherman signed the Constitution and authored the Connecticut Compromise; George Washington stayed at his house in 1789.
Q 21Louis' Lunch burgers are served on what instead of a bun?
Two slices of toasted white bread
The bread goes through a 1929 Savory Radiant Gas Toaster; the only toppings allowed are cheese spread, tomato and onion.
Q 22New Haven-style pizza is known locally by what name?
Apizza
It is baked in coal- or wood-fired brick ovens with a thin, charred crust, and a 'plain' pie comes without mozzarella.
Q 23Which seafood tops the signature 'white pie' of Wooster Street's pizzerias?
Clams
A white pie uses garlic and olive oil instead of tomato sauce; Pepe's original 1925 menu offered only a tomato pie and an anchovy pie.
Q 14Which Yale graduate stayed in New Haven to develop the cotton gin and build a gun factory?
Eli Whitney
The neighborhood is still called Whitneyville, and his factory is now a museum with a heavy focus on children's activities.
Q 15Whose statue stands beside New Haven's City Hall, commemorating the 1839 Amistad trial held in the city?
Joseph Cinqué
The memorial stands on the site of the jail that held the captives; spectators paid twelve and a half cents to view them.
Q 16Which gunmaker produced firearms in New Haven until 2006?
Winchester Repeating Arms
It grew out of the New Haven Arms Company, which boomed on Civil War orders.
Q 17Which Catholic fraternal organization was founded at St. Mary's Church in New Haven in 1882?
The Knights of Columbus
Its 23-story headquarters is the third-tallest building in the city, and its founder, Father Michael McGivney, has been beatified.
Q 18In 1878, the District Telephone Company of New Haven created the world's first what?
Switchboard exchange
It also produced the first telephone directory and installed the first public phone, and it later became Southern New England Telephone.
Q 19Louis' Lunch on Crown Street is credited by the Library of Congress with inventing what in 1900?
The hamburger
The family story says a hurried customer asked Louis Lassen to 'slap a meatpuck between two planks', so he served ground steak between two slices of toast.
Q 20Louis' Lunch is famous for ejecting customers who ask for which condiment?
Ketchup
A sign inside reads 'This is not Burger King. You don't get it your way.' The burgers are broiled vertically in cast-iron stoves from 1898.
Q 24Frank Pepe emigrated to New Haven as a teenager from which Italian town?
Maiori
Before opening his pizzeria in 1925 he sold 'tomato pies' around the Wooster Square market from a special headdress and later a wagon.
Q 25Sally's, Pepe's great rival on Wooster Street, was bought in 1938 for $500 by whom?
Frank's sister, Filomena Consiglio
Filomena Consiglio's son Sal ran it until his death in 1989, and the family sold the business to an unnamed buyer in 2017.
Q 26Modern, the third of New Haven's famous pizzerias, opened in 1934 on which downtown thoroughfare?
State Street
It opened in 1934, nine years after Pepe's and four years before Sally's.
Q 27The Frisbee is named after a Connecticut company whose tins Yale students tossed. What did it make?
Pies
Wham-O adopted the name in 1957 after hearing students call its Pluto Platter a 'Frisbie', after the Frisbie Pie Company.
Q 28Confectioner George Smith of New Haven named his stick-mounted candy after what?
A racehorse
He started making the candies in 1908 and trademarked the 'lollipop' name in 1931.
Q 29Which construction toy was invented in New Haven by A. C. Gilbert in 1911?
The Erector Set
Gilbert was also an Olympic pole-vault gold medalist and a working magician; his inspiration was the steel girders of the New Haven Railroad.
Q 30A. C. Gilbert earned the nickname 'The man who saved Christmas' for doing what in 1918?
Talking the government out of banning toy production
The Council of National Defense was weighing a wartime ban on toys; Gilbert argued successfully against it.