Long Island
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52 free Long Island trivia questions with answers — geography quiz, new questions added Oct 2026.
55 free Long Island trivia questions with answers. Long Island is 118 miles of contradictions: the country's biggest island that the Supreme Court says is not legally an island, home to Gatsby's mansions and the first mass-produced suburb, the factory that built the lunar module and the bar that (probably) invented a cocktail with no tea in it. This quiz covers the whole thing, from Brooklyn and Queens out to Orient and Montauk Points: geography, the Battle of Long Island, the LIRR, Levittown, Roosevelt Field, Brookhaven and Cold Spring Harbor, Jones Beach and Fire Island, the Islanders and Belmont, wine, ducks, the Hamptons, and famous Long Islanders. Questions start easy (which sound lies to the north, where the Hamptons are) and climb to genuinely hard ones about the Dutch name on 1650s maps, Jayne's Hill and the first vinifera vineyard. Every answer was checked against a documented source and the citation sits under each explanation, so a Nassau-versus-Suffolk argument can be settled on the spot. Play it solo, or use it as a Long Island round for a bar trivia night from Massapequa to Montauk.
30 of 52 questions with answers and explanations. Play the quiz
Q 01Long Island covers more land than which entire US state?
Rhode Island
Rhode Island. The smallest state has about 1,034 square miles of land to the island's 1,400 or so, while Delaware, the next smallest, could still hold the island with room to spare.
Q 02Which inventor built Wardenclyffe Tower at Shoreham, Long Island, hoping to send messages and power without wires?
Nikola Tesla
Nikola Tesla. He began the tower in 1901 with money from the banker J. P. Morgan, but the funding ran out and it was torn down for scrap in 1917 to help pay his debts.
Q 03Which two of Long Island's four counties are also boroughs of New York City?
Kings and Queens
Kings and Queens are New York City boroughs: Kings County is Brooklyn and Queens County is the borough of the same name. Nassau and Suffolk make up what most people mean by 'the Island.'
Q 04Which pirate left treasure on Gardiners Island, off Long Island's East End, in 1699?
Captain Kidd
Captain Kidd. He stopped at the island on his way to Boston to answer piracy charges, and after his arrest the governor had the hoard collected to use as evidence against him.
Q 05What formed Long Island's two east-west ridges, Harbor Hill and Ronkonkoma?
Ice Age glaciers
Ice Age glaciers piled up both ridges as moraines of gravel and loose rock, and blocks of ice they left behind melted into deep kettle lakes such as Lake Ronkonkoma.
Q 06Which hill, at roughly 400 feet, is the highest natural point on Long Island?
Jayne's Hill
Jayne's Hill stands in West Hills County Park, where a poet born at its foot came back in 1881 and wrote that he might be standing on the highest spot on Long Island.
Q 07Which painter moved to Springs, on Long Island's East End, in 1945 and lived there until his death?
Jackson Pollock
Jackson Pollock. There he began laying canvases flat on his studio floor and dripping paint over them; the house he shared with the painter Lee Krasner is now a museum and a National Historic Landmark.
Q 08In United States vs. Maine (1985), the Supreme Court ruled Long Island is legally what?
Part of the mainland
Part of the mainland. The justices treated the island as an extension of the shore, which turned the waters behind it into a bay controlled by the states instead of the federal government.
Q 09The far eastern tip of the North Fork, where the ferry to New London departs, is called what?
Orient Point
Orient Point is where the car ferry leaves for New London, Connecticut; one of the boats on the run, the Cape Henlopen, is a converted landing ship that took part in the D-Day landings in Normandy.
Q 10The Battle of Long Island in August 1776 holds what distinction in the Revolutionary War?
Biggest engagement of the war
Biggest engagement of the war by troops involved, it was also the first major battle after the Declaration of Independence, and the defeat cost the Americans New York City.
Q 11How did Washington save his army after losing the Battle of Long Island?
A night evacuation across the East River
A night evacuation across the East River saved the army: on August 29-30, 1776, about 9,000 men were ferried to Manhattan under darkness and fog without the loss of a single life.
Q 12The Long Island Rail Road bills itself as the oldest US railroad still doing what?
Operating under its original name and charter
Operating under its original name and charter since April 1834, the LIRR was first meant to be part of a New York-to-Boston route via a ferry from Greenport, not a commuter line.
Q 13What is the LIRR's second Manhattan terminal, opened in January 2023, called?
Q 21Which Long Island aircraft maker built the Apollo lunar modules that carried astronauts to the Moon's surface?
Grumman
Grumman assembled the landers at its Long Island plant, and one of them, Aquarius, became the lifeboat that kept the Apollo 13 crew alive after their main spacecraft was crippled.
Q 22Which Long Island lab, on the old Camp Upton army base, produced Tennis for Two in 1958?
Brookhaven National Laboratory
Brookhaven National Laboratory physicist William Higinbotham wired an analog computer to an oscilloscope to liven up the lab's visitors' day, and hundreds of people queued to play.
Q 23Which Long Island institution was run for decades by James Watson and counts eight Nobel laureates?
Grand Central Madison
Grand Central Madison is named for the Madison Avenue corridor above it; work on the project began in 2008, and its budget grew from about $4 billion to more than $11 billion.
Q 14Levittown, the prototype postwar suburb, was called what when Levitt & Sons broke ground in 1947?
Island Trees
Island Trees is what Levitt & Sons first called the development in 1947 before renaming it after themselves; by July 1948 their crews were turning out 30 houses a day.
Q 15Levittown's original leases contained a covenant restricting occupancy to whom?
Members of the Caucasian race
Members of the Caucasian race were the only occupants clause 25 of the first leases allowed; the Supreme Court made such covenants unenforceable in 1948, yet the builders kept turning away Black buyers.
Q 16Which financier built Oheka Castle on Long Island, the second-largest private home in the United States?
Otto Kahn
Otto Kahn made the name from his own, Otto Hermann Kahn; the 127-room house later stood in for Xanadu in Citizen Kane and was the setting of Taylor Swift's 'Blank Space' video.
Q 17Which nickname did Long Island's North Shore earn for the mansions tycoons built there from the late 1800s?
The Gold Coast
The Gold Coast. Its era of great estates ended with new taxes, the Depression and rising upkeep costs, and many owners subdivided the land or gave the houses to parks and preservation groups.
Q 18Which real Long Island peninsula, where Fitzgerald lived from 1922 to 1924, was the model for Gatsby's West Egg?
Great Neck
Great Neck became new-money West Egg and Sands Point, across the bay, old-money East Egg; the ash dumps behind the novel's 'valley of ashes' are now Flushing Meadows-Corona Park.
Q 19Charles Lindbergh took off for Paris in 1927 from which Long Island airfield, now a shopping mall site?
Roosevelt Field
Roosevelt Field was named for Theodore Roosevelt's son Quentin, a pilot killed in air combat in 1918; Lindbergh left it on May 20, 1927, and the field closed in 1951 to become a shopping center.
Q 20Long Island's cluster of pioneering airfields earned it which nickname?
The Cradle of Aviation
The Cradle of Aviation is also the name of the museum in Garden City, whose prize exhibit is a real Apollo lunar module that never flew because its Moon mission was cancelled.
Cold Spring Harbor Laboratory
Cold Spring Harbor Laboratory was led by James Watson from 1968 to 2007 as director, president and chancellor; its darkest chapter was hosting the Eugenics Record Office from 1910 to 1939.
Q 24Which poet was born in 1819 in a West Hills farmhouse and raised in Brooklyn?
Walt Whitman
Walt Whitman was born in the West Hills farmhouse now kept as a state historic site, and after a spell of teaching he came back to Huntington to start his own newspaper, the Long-Islander.
Q 25The Montauk Point Light was authorized under which president?
George Washington
George Washington was president when Congress authorized the light in 1792; finished in 1796, it stood 300 feet back from the cliff edge, a margin that erosion has since cut to about 100 feet.
Q 26Fire Island National Seashore was created in 1964 largely in response to protests against what?
A proposed highway
A proposed highway along the barrier island, pushed by Robert Moses, sparked the protests that led Congress to create the seashore; even now cars can reach only the two ends of Fire Island.
Q 27Which Fire Island community is known as 'America's First Gay and Lesbian Town'?
Cherry Grove
Cherry Grove's Community House and Theatre, where residents began staging shows in 1948, joined the National Register of Historic Places in 2013 for its part in that history.
Q 28The Power Broker alleged Robert Moses built parkway bridges deliberately low to keep out what?
Buses
Buses could not clear the low overpasses, Caro wrote, which kept poorer families without cars away from Jones Beach; critics reply that low bridges were standard on parkways of the time.
Q 29The Long Island Expressway, Interstate 495, ends in which Suffolk town at its eastern terminus?
Riverhead
Riverhead is where the expressway finally gives out; its chronic jams had earned it the nickname 'the world's longest parking lot' in print by 1963.
Q 30Nassau County was carved out in 1899 from the eastern 70 percent of which existing county?
Queens
Queens County split after its western part joined New York City in 1898: the three eastern towns left outside the city broke away as Nassau County on January 1, 1899.