U.S. Military History
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50 free U.S. Military History trivia questions with answers — history quiz, new questions added Oct 2026.
American military history is a long run of close calls and unlikely turns. A ragged colonial army outlasted the strongest empire of its day, a civil war nearly split the country in two, and within a century the United States was fighting on oceans and continents far from home. Behind the famous dates are the details people remember: a desperate river crossing, a message nobody should have been able to read, a nickname that stuck for two hundred years. This quiz covers the whole sweep. Expect the War of Independence, the War of 1812, the Civil War, the frontier and the war with Spain, both world wars, Korea, Vietnam and the conflicts since. The questions take in battles, commanders, ships, medals, traditions and the ordinary men and women in uniform who became part of the legend. It is written for history fans, veterans and their families, students and anyone hosting a trivia night. Every answer comes with a short explanation, so even a wrong guess leaves you with a story worth repeating.
30 of 50 questions with answers and explanations. Play the quiz
Q 01Which 1775 battle near Boston was a British victory so costly that it encouraged the American rebels?
Bunker Hill
Bunker Hill was fought mostly on neighboring Breed's Hill, where colonial troops had dug a redoubt overnight. The British took the ground, but the price made it a Pyrrhic win.
Q 02Which national nickname does legend trace to a New York meatpacker who supplied army rations in the War of 1812?
Uncle Sam
Uncle Sam, the story goes, began as a joke about the U.S. initials stamped on meatpacker Samuel Wilson's ration packages. Historians call the true origin obscure.
Q 03Which abolitionist led Union soldiers on an 1863 raid up South Carolina's Combahee River that freed over 700 people?
Harriet Tubman
Harriet Tubman led 150 Black soldiers of the 2nd South Carolina Infantry on the raid, and many of the people they freed went on to join the Union Army.
Q 04Which US decoration descends from the Badge of Military Merit that George Washington created in 1782?
Purple Heart
The Purple Heart, now given to troops wounded or killed in action, revives Washington's award: a heart of purple cloth that he gave to only three Revolutionary War soldiers.
Q 05Which bugle call did Union general Daniel Butterfield arrange in 1862 as a new signal for lights out?
Taps
Taps began as Butterfield's lights-out call. That same summer an artillery captain, unable to fire the usual three volleys so close to the enemy, had it sounded at a burial instead, and the custom spread.
Q 06Which name did American troops in World War II scrawl beside a doodle of a bald man peeking over a wall?
Kilroy
Kilroy turned up wherever American servicemen were stationed, encamped or visited. Nobody knows whether a real person inspired the name, though a shipyard inspector later claimed it.
Q 07Which Native American language did US Marine code talkers use for radio messages in the Pacific in World War II?
Navajo
Navajo was proposed to the Marines by Philip Johnston, a missionary's son raised on the reservation. With no word for submarine, the code talkers called it an iron fish.
Q 08Which Baltimore stronghold withstood the 1814 British bombardment that inspired Francis Scott Key's national anthem?
Fort McHenry
Fort McHenry is a pentagon-shaped fort whose pointed bastions could cover one another with crossfire. The sight of its flag still flying gave Key his poem.
Q 09Which future president won the Battle of New Orleans in 1815, fought two weeks after the peace treaty was signed?
Andrew Jackson
Andrew Jackson beat the British 15 days after the Treaty of Ghent was signed, because news of the peace had not yet crossed the Atlantic.
Q 10Which later president was skipper of PT-109 when a Japanese destroyer rammed and sank the torpedo boat in 1943?
John F. Kennedy
John F. Kennedy saved his surviving crew, later scratching a rescue message on a coconut, and the episode made him a war hero.
Q 11Which Massachusetts woman disguised herself as a man to serve in the Continental Army and was shot in the thigh?
Deborah Sampson
Deborah Sampson joined an elite unit picked for size and strength, which helped her disguise: nobody was likely to look for a woman among those soldiers.
Q 12Which icy river did George Washington's army cross on Christmas night 1776 to surprise the Hessians at Trenton?
Delaware
Delaware River ice made the night crossing a gamble, but it set up a surprise attack on the garrison the next morning. Emanuel Leutze turned the scene into his idealized 1851 painting.
Q 13At which Pennsylvania winter camp of 1777–78 did Prussian drillmaster Baron von Steuben retrain the Continental Army?
Valley Forge
Q 21Which island stronghold in Charleston Harbor was bombarded in April 1861, firing the opening shots of the Civil War?
Fort Sumter
Fort Sumter fell without a single death in the bombardment. The war's first military fatalities came during the surrender salute, when a pile of cartridges blew up.
Q 22Which 1862 battle in Maryland remains the bloodiest single day in American history, with over 22,000 casualties?
Antietam
Antietam's outcome gave Lincoln the political confidence to issue the preliminary Emancipation Proclamation five days later.
Q 23At which 1863 Pennsylvania battle did the failure of Pickett's Charge mark the high-water mark of the Confederacy?
Gettysburg
Valley Forge turned the army around: under Steuben the Continentals practiced volley fire, standardized their marching pace and drilled with the bayonet.
Q 14Which 1777 American victory in upstate New York, where General Burgoyne surrendered, persuaded France to join the war?
Saratoga
Saratoga proved the rebels could beat a British army in the field. France had been slipping the Americans guns in secret, and the news turned that help into an open alliance.
Q 15At which Virginia port did Lord Cornwallis's British army surrender in 1781, all but ending the Revolutionary War?
Yorktown
Yorktown's surrender ceremony went ahead without Cornwallis, who pleaded illness. His deputy tried to surrender to the French commander, who pointed him toward Washington.
Q 16Which Continental Army general secretly plotted in 1780 to hand the Hudson River fort at West Point to the British?
Benedict Arnold
Benedict Arnold fled to the British when militiamen caught Major John André carrying papers that revealed the plot. André was hanged; Arnold became a British brigadier and a byword for treason.
Q 17Which North African state declared war on the US in 1801 over tribute payments, starting the First Barbary War?
Tripoli
Tripoli gives the conflict its other name, the Tripolitan War. During it, William Eaton led a handful of Marines and several hundred mercenaries across the desert to capture the city of Derna.
Q 18Which captain, often called the Father of the American Navy, fought HMS Serapis in the Bonhomme Richard in 1779?
John Paul Jones
John Paul Jones knew he could not win a duel of big guns, so he worked to lock the two ships together. He later became a rear admiral in the Imperial Russian Navy.
Q 19Which US Navy frigate earned the nickname Old Ironsides by capturing HMS Guerriere during the War of 1812?
USS Constitution
USS Constitution is still in commission and is the oldest commissioned warship afloat. She sailed under her own power for her 200th birthday in 1997.
Q 20Which war ended with the 1848 Treaty of Guadalupe Hidalgo, which handed California and much of the Southwest to the US?
Mexican–American War
The Mexican–American War cost Mexico 55 percent of its territory, including present-day California, Nevada and Utah. US troops had taken the capital months earlier.
Gettysburg's climactic assault is named for Major General George Pickett, though he was just one of the Confederate division commanders who took part.
Q 24Which Mississippi River fortress city surrendered on 4 July 1863 after a siege of more than 40 days?
Vicksburg
Vicksburg's fall, followed days later by Port Hudson, put the whole river firmly in Union hands and split the Confederacy in two.
Q 25Which Union general won the nickname Unconditional Surrender after capturing Fort Donelson in Tennessee in 1862?
Ulysses S. Grant
Ulysses S. Grant had demanded exactly those terms from the fort's commander, and the Northern press noticed that the phrase matched his initials.
Q 26Which Virginian was offered a senior Union command in April 1861 but instead became the Confederacy's leading general?
Robert E. Lee
Robert E. Lee received the offer just three weeks after being promoted to colonel in the US Army. He resigned his commission instead.
Q 27Which Union general presented the captured city of Savannah to President Lincoln as a Christmas gift in 1864?
William T. Sherman
William T. Sherman had marched from Atlanta to the sea, his men heating railroad rails over fires and twisting them around trees into what became known as Sherman's neckties.
Q 28At which Virginia village did the Army of Northern Virginia surrender in April 1865, effectively ending the Civil War?
Appomattox Court House
Appomattox Court House hosted the surrender in the parlor of Wilmer McLean, who had moved there to escape the war after its first big battle was fought on his farm.
Q 29Which Civil War nurse, nicknamed the Angel of the Battlefield, went on to found the American Red Cross?
Clara Barton
Clara Barton earned the name by coming to the aid of an overwhelmed surgeon after the battle of Cedar Mountain in 1862. Before the war she had worked as a patent clerk.
Q 30At which 1876 Montana battle did Lakota and Cheyenne warriors wipe out George Custer's 7th Cavalry detachment?
Little Bighorn
Little Bighorn is known to the Lakota as the Battle of the Greasy Grass. Their war leaders included Crazy Horse and Gall, inspired by the visions of Sitting Bull.