60 free Long Island trivia questions with answers — geography quiz, new questions added Aug 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 60 questions with answers and explanations. Play the quiz
Q 01Long Island stretches how far east from New York Harbor into the Atlantic?
118 miles
At its widest the island is only 23 miles across, which is why locals give directions purely in terms of 'north shore' and 'south shore.'
Q 02Long Island's eight million-plus people are roughly what share of New York State's population?
40%
That makes it the most populous island in any US state or territory, and it would rank around 12th among the states if it were one.
Q 03Which two of Long Island's four counties are also boroughs of New York City?
Kings and Queens
Kings County is Brooklyn. Nassau and Suffolk make up what most people mean when they say 'the Island.'
Q 04The 1650s Dutch name for the island, 't Lange Eylandt, was paired on maps with what Native American name?
Matouwacs
Walt Whitman preferred the Algonquian name Paumanok, which he used in his poetry.
Q 05Long Island's two east-west ridges, the Harbor Hill and Ronkonkoma moraines, were left behind by what?
Ice Age glaciers
The debris dates from the last pulses of Wisconsin glaciation about 21,000 years ago; the same ice scooped out the kettle lakes Ronkonkoma and Success.
Q 06What is the highest natural point on Long Island, at a modest 401 feet?
Jayne's Hill
It sits in West Hills near the Nassau-Suffolk line, a short walk from Walt Whitman's birthplace.
Q 07Why are the island's northern beaches rocky while its southern beaches are fine white sand?
Glacial debris vs glacial outwash
The South Shore's sand is fronted by a chain of barrier islands, including Fire Island and Jones Beach Island.
Q 08In United States v. Maine (1985), the Supreme Court ruled Long Island is legally what?
Part of the mainland
The ruling turned Long Island Sound into a 'juridical bay', though the Board on Geographic Names still calls it an island because it is surrounded by water.
Q 09The far eastern tip of the North Fork, where the ferry to New London departs, is called what?
Orient Point
The two forks split near the county seat; the North Fork is now better known for its wineries than its potato farms.
Q 10The Battle of Long Island, fought on August 27, 1776, holds what distinction in the Revolutionary War?
Biggest engagement of the war
It was also the first major battle after the Declaration of Independence; the British held New York and Long Island until 1783.
Q 11How did Washington save his army after losing the Battle of Long Island?
A night evacuation across the East River
About 9,000 men were ferried to Manhattan under cover of darkness and fog without a single loss of life.
Q 12The Long Island Rail Road, chartered in 1834, is the oldest US railroad still doing what?
Operating under its original name and charter
It was originally meant to be part of a New York-to-Boston route via a ferry from Greenport, not a commuter line.
Q 13The LIRR gained a second Manhattan terminal in January 2023. What is it called?
Q 21The Apollo Lunar Module was assembled in which Long Island town?
Bethpage
Grumman had moved there in 1939 after starting out in a Baldwin garage; the same plant later built the F-14 Tomcat.
Q 22For how many hours was Apollo 13's lunar module Aquarius designed to support two astronauts?
45
Grumman engineers reportedly joked about sending North American Rockwell a towing bill for the command module.
Q 23Which Long Island lab, on the old Camp Upton army base, produced Tennis for Two in 1958?
Brookhaven National Laboratory
Seven Nobel Prizes have come out of work done there, and it now runs the Relativistic Heavy Ion Collider.
Grand Central Madison
The East Side Access project took more than a decade and gave the busiest commuter railroad in North America a direct route to Grand Central.
Q 14Levittown, the prototype postwar suburb, was called what when Levitt & Sons broke ground in 1947?
Island Trees
By July 1948 the company was finishing 30 houses a day, and its ranch homes sold for $7,990 in 1949.
Q 15Levittown's original leases contained a covenant restricting occupancy to whom?
Members of the Caucasian race
Sales agents also turned away Black, Asian and Jewish families; the town stayed nearly all-white for decades after Brown v. Board.
Q 16Which industrialist's Long Island estate, Oheka Castle, is the second-largest US private home?
Otto Kahn
The name is built from his initials, Otto Hermann Kahn; the 127-room house later doubled as Xanadu in Citizen Kane and starred in Taylor Swift's 'Blank Space' video.
Q 17Roughly how many Gold Coast mansions went up on the North Shore during its Gilded Age building spree?
Over 500
Around 300 were torn down after World War II; the survivors include Old Westbury Gardens and the Vanderbilt Museum.
Q 18Which real Long Island peninsula, where Fitzgerald lived from 1922 to 1924, was the model for Gatsby's West Egg?
Great Neck
Old-money East Egg was Sands Point across Manhasset Bay; the 'valley of ashes' between them and the city was the Corona ash dumps, later Flushing Meadows.
Q 19Charles Lindbergh took off for Paris in 1927 from which Long Island airfield, now a shopping mall site?
Roosevelt Field
The field was renamed in 1919 for Theodore Roosevelt's son Quentin, killed in air combat in World War I; it closed in 1951.
Q 20Long Island's cluster of early airfields earned it what nickname by the mid-1920s?
The Cradle of Aviation
The museum of that name in Garden City holds a real Lunar Module, LM-13, built for the cancelled Apollo 19 mission.
Q 24Which Long Island institution was run for decades by James Watson and counts eight Nobel laureates?
Cold Spring Harbor Laboratory
Its darkest chapter was hosting the Eugenics Record Office from 1910 to 1939.
Q 25Theodore Roosevelt's home Sagamore Hill overlooks which Long Island harbor?
Oyster Bay
He died there on January 6, 1919 and is buried nearby at Youngs Memorial Cemetery.
Q 26Which poet was born in 1819 in a West Hills farmhouse and moved to Brooklyn at age five?
Walt Whitman
The house is a state historic site; a nearby shopping mall borrows his name too.
Q 27The Montauk Point Light, completed in 1796, was authorized under which president?
George Washington
It was New York's first lighthouse and is the fourth-oldest still active in the country.
Q 28The 168-foot Fire Island Lighthouse, lit in 1858, was decommissioned in 1974 and then what?
Relit in 1986 after a preservation campaign
It was the first sight of America for generations of immigrants arriving by ship, and later played a cameo in Men in Black II.
Q 29Fire Island National Seashore was created in 1964 largely in response to protests against what?
A proposed highway
Most of the 31-mile barrier island is still car-free; residents haul groceries in wagons along boardwalks.
Q 30Which Fire Island community calls itself 'America's First Gay and Lesbian Town'?
Cherry Grove
Cherry Grove and neighboring Fire Island Pines were established LGBT havens by the 1950s.