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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.
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Q 01New Haven sits on the northern shore of which body of water?
Long Island Sound
New Haven Harbor, fed by three rivers, is a shallow embayment of Long Island Sound, the tidal estuary separating Connecticut from Long Island.
Q 02New Haven's nickname, 'The Elm City', traces back to what civic innovation?
The first public tree-planting program in the US
New Haven's late-18th-century public tree-planting program, the first in the US, lined its streets with elms; that canopy earned the city the nickname The Elm City.
Q 03New Haven's original 1638 street layout is known by what name?
The Nine Square Plan
The Nine Square Plan laid out a three-by-three grid of blocks with the central square kept open as the Green; the American Planning Association lists it as a National Planning Landmark.
Q 04Roughly how large is the New Haven Green?
16 acres
The Green covers about 16 acres at the center of the original town grid; legend says the Puritans sized it to hold the 144,000 they believed would be saved 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
Minister John Davenport and merchant Theophilus Eaton led the group, seeking a stricter Puritan settlement than Massachusetts; Eaton served as the colony's governor until his death in 1658.
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
Judges' Cave, a cluster of boulders atop West Rock, hid regicides Edward Whalley and William Goffe from royal agents in 1661; the ridge path is named the Regicides Trail.
Q 09Which year's statewide vote chose Hartford over New Haven as Connecticut's sole capital?
1873
Voters chose Hartford in 1873, ending the arrangement that since 1701 had alternated legislative sessions between New Haven and Hartford; the change took effect in 1875.
Q 10Yale moved to New Haven in 1716 from which Connecticut town?
Old Saybrook
The Collegiate School had been seated at Saybrook, today's Old Saybrook, since 1701; it moved to New Haven in 1716 and took Elihu Yale's name in 1718.
Q 11Elihu Yale, whose 1718 gift renamed the Collegiate School, made his fortune as governor of which outpost?
Madras
Elihu Yale governed the East India Company's Fort St. George at Madras from 1687 to 1692; his nine bales of goods sold for over £560, and Cotton Mather proposed naming the college for him.
Q 12Which future traitor led New Haven's Foot Guard to seize the powder house in 1775?
Benedict Arnold
Captain Benedict Arnold demanded the keys to the powder house after news of Lexington arrived, then marched his Foot Guard to Cambridge; New Haven re-enacts the episode each spring as Powder House Day.
Q 13Who became New Haven's first mayor when it was incorporated as a city in 1784?
Roger Sherman
Q 21Louis' Lunch serves its signature sandwich on what instead of a bun?
Two slices of toasted white bread
Each patty goes between two slices of toasted white bread run 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
Apizza, pronounced 'ah-BEETS', is baked in coal-fired brick ovens with a thin, charred crust; a 'plain' pizza comes with tomato sauce and grated pecorino but no mozzarella.
Q 23Which seafood tops the signature 'white pie' of Wooster Street's pizzerias?
Clams
Roger Sherman, a signer of the Declaration and the Constitution and author of the Connecticut Compromise, served as New Haven's mayor from 1784 until his death in 1793.
Q 14Which Yale graduate stayed in New Haven to develop the cotton gin and build a gun factory?
Eli Whitney
Eli Whitney built his armory on the Mill River in 1798 to make muskets for the federal government; the neighborhood became Whitneyville, and the site houses the Eli Whitney Museum.
Q 15Whose statue beside New Haven's City Hall commemorates the Amistad captives jailed in the city?
Joseph Cinqué
Ed Hamilton's 1992 Amistad Memorial depicts Joseph Cinqué, also called Sengbe Pieh, leader of the 1839 revolt; it stands on the site of the jail that held the captives during their trial.
Q 16Which gunmaker produced firearms in New Haven until 2006?
Winchester Repeating Arms
Winchester Repeating Arms, formed in 1866 from the New Haven Arms Company, made rifles on Winchester Avenue until its successor, U.S. Repeating Arms, closed the plant in 2006.
Q 17Which Catholic fraternal organization was founded at St. Mary's Church in New Haven in 1882?
The Knights of Columbus
The Knights of Columbus were founded at St. Mary's in 1882 by Father Michael McGivney, beatified in 2020; the order's 23-story headquarters tower stands beside the downtown highway connector.
Q 18In 1878, the District Telephone Company of New Haven created the world's first what?
Switchboard exchange
The company opened the world's first commercial telephone exchange, a switchboard serving 21 subscribers, on January 28, 1878; it issued the first telephone directory weeks later and grew into Southern New England Telephone.
Q 19Louis' Lunch on Crown Street is credited by the Library of Congress with inventing what in 1900?
The hamburger
Louis Lassen served a hurried customer a ground-steak patty as a sandwich in 1900, and the Library of Congress credits Louis' Lunch with inventing the hamburger.
Q 20Louis' Lunch is famous for ejecting customers who ask for which condiment?
Ketchup
Ketchup is banned at Louis' Lunch, which allows only cheese, tomato and onion; the meat is broiled vertically in cast-iron gas stoves dating from 1898.
Pepe's white clam pizza tops a garlic-and-olive-oil base with freshly shucked littleneck clams; the original 1925 menu offered only tomato pizza, with or without anchovies.
Q 24Frank Pepe emigrated to New Haven as a teenager from which Italian town?
Maiori
Pepe left Maiori, on the Amalfi Coast, in 1909 at age 16; before opening his pizzeria in 1925 he peddled tomato pizzas around Wooster Square, balancing them on his head and later from 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
Frank Pepe's sister Filomena Consiglio bought the Wooster Street property for $500 in 1938; her son Salvatore 'Sally' Consiglio ran the pizzeria until his death in 1989.
Q 26Modern, the third of New Haven's famous pizzerias, opened in 1934 on which downtown thoroughfare?
State Street
Modern opened on State Street in 1934, nine years after Pepe's and four before Sally's; unlike its coal-fired rivals it bakes in an oil-fired brick oven.
Q 27The Frisbee takes its name from which product's tins, tossed by Yale students?
Pies
Bridgeport's Frisbie Pie Company baked pies whose empty tins Yale students flung; Wham-O renamed its Pluto Platter the Frisbee after hearing students call the disc a 'Frisbie'.
Q 28Confectioner George Smith of New Haven named his stick-mounted candy after what?
A racehorse
Smith said he named the candy after Lolly Pop, a racehorse of the day; he began making the sticks 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's Erector Set, sold from 1913, was inspired by the steel girders he saw going up for the New Haven Railroad's electrification; he was also a 1908 Olympic pole-vault champion and a working magician.
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.