Deborah Sampson
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40 free Deborah Sampson trivia questions with answers — history quiz, new questions added Oct 2026.
Deborah Sampson is one of the few women known to have fought in the Revolutionary War. In 1782 she put on men's clothes, gave a false name and joined the Continental Army, where she marched, scouted and was wounded in action before anyone learned her secret. These questions follow the fun facts people look for about her: a hard childhood in colonial Massachusetts, two attempts to enlist, the injury she treated herself, the illness that exposed her, and the years she spent afterwards fighting to be paid. They also cover how she is remembered today, on screen, in law and in her home state. The quiz suits students working on a report, teachers planning a Revolutionary War lesson, and anyone who enjoys a true story stranger than fiction. Every answer comes with a short explanation.
30 of 40 questions with answers and explanations. Play the quiz
Q 01Which famous Boston Patriot lent Deborah Sampson money and wrote to a congressman on her behalf?
Paul Revere
Paul Revere sent her the ten dollars she asked to borrow in 1806. His letter to a congressman vouched for her character after he had asked around about her.
Q 02Under which male alias did Deborah Sampson serve 17 months in the Continental Army?
Robert Shirtliff
Robert Shirtliff was the name she gave the 4th Massachusetts Regiment, and records also spell it Shurtleff. The other three were real men in her story: her future husband, her captain and her colonel.
Q 03Which comedian voiced Deborah Sampson in the animated history series Liberty's Kids?
Whoopi Goldberg
Whoopi Goldberg joined a starry voice cast that had Walter Cronkite as Benjamin Franklin and Ben Stiller as Thomas Jefferson. Her episode aired in 2003.
Q 04Which actress cited Deborah Sampson in a speech at the 2016 Democratic National Convention?
Meryl Streep
Meryl Streep set Deborah Sampson beside other women who had made history, putting a soldier of the 1780s in front of a prime-time audience more than two centuries later.
Q 05After a 1782 skirmish, Deborah Sampson cut a ball out of her own thigh using what?
A penknife and needle
A penknife and needle let her dodge the doctors who might have found her out, so she left the hospital with the leg untreated. Some shot stayed too deep to reach, and the wound never fully healed.
Q 06In which city did a doctor treating Deborah Sampson for fever discover her secret in 1783?
Philadelphia
Philadelphia is where she passed out with fever and a doctor found the cloth binding her chest. He told no one in the Army and moved her to his own house to recover.
Q 07In 1802, Deborah Sampson became one of the first American women to do what, often in uniform?
Go on a lecture tour
To go on a lecture tour was almost unheard of for a woman in 1802. She closed each talk by coming back on stage in Army uniform and running through a demanding military drill.
Q 08In 1983, the Commonwealth of Massachusetts proclaimed Deborah Sampson its official what?
Heroine
Heroine is her official state title, proclaimed on May 23, 1983. The town where she was born later put her on its flag.
Q 09Which physical trait, rare in women of the 1700s, helped Deborah Sampson pass as a male soldier?
Her height
Her height, about five feet seven, beat the average man of her day by a couple of inches. She joined a company picked for size, where nobody thought to look for a woman.
Q 10Four years after Deborah Sampson died, her husband asked Congress for what as a soldier's spouse?
A pension
A pension was approved for Benjamin Gannett in 1837, by a committee that said the Revolution offered no other case like his wife's. He died before he could collect it.
Q 11In which Massachusetts town was Deborah Sampson born, in a grandparents' house that still stands?
Plympton
Plympton lies near Plymouth, where her Pilgrim ancestors settled. The town green has carried a bronze plaque in her memory since 1906.
Q 12Deborah Sampson's mother was a great-granddaughter of which longtime governor of Plymouth Colony?
William Bradford
William Bradford led Plymouth Colony on and off for about 30 years. His descendant still grew up in poverty, raised in other families' homes.
Q 13Deborah Sampson's family was told that her missing father had died in what way?
In a shipwreck
In a shipwreck was the family story, but the evidence says Jonathan Sampson simply walked out. He started a second household elsewhere and lived for decades more.
Q 21Deborah Sampson was wounded in 1782 when her patrol fought a local band of which enemy?
Tories
Tories, colonists loyal to the Crown, clashed with her unit in Westchester County, north of British-held New York City. Her company scouted the contested ground between the two armies.
Q 22What weapon gashed Deborah Sampson's forehead in the same 1782 fight in which she was shot?
A sword
A sword cut was the one wound she let a doctor treat, since a head injury posed no risk to her disguise. She left the hospital before he could look at her leg.
Q 23Deborah Sampson spent seven months of 1783 as a waiter to which Continental Army general?
John Paterson
Q 14Deborah Sampson's father abandoned his family and resettled in which district, later a state?
Maine
Maine is where he took a common-law wife named Martha and had at least two more children. He came back to his old hometown in 1794 to see to a property deal.
Q 15From age 10 to 18, Deborah Sampson lived with a Middleborough farm family in what role?
Indentured servant
Indentured servant was her status in the Thomas household, where she was treated well but kept out of school. The head of the family did not believe in educating women.
Q 16At 18 and newly independent, Deborah Sampson spent two summers doing which job?
Teaching school
Teaching school was a bold step for someone never sent to class herself. She had picked up her lessons from the schoolwork the sons of the household shared with her.
Q 17Which church cut off Deborah Sampson after she first tried to enlist dressed as a man?
Baptist
Baptist members withdrew their fellowship and refused to associate with her unless she apologised and asked forgiveness. By the time they voted, she had already left town and joined the Army.
Q 18Deborah Sampson's second enlistment, in May 1782, filled a soldier quota for which Massachusetts town?
Uxbridge
Uxbridge got the credit for her service: she signed on at Bellingham, for a bounty, to fill one of Uxbridge's places in the Army. A first try closer to home had ended when a local recognised her.
Q 19Deborah Sampson served in which kind of elite company, hand-picked for size and strength?
Light infantry
Light infantry companies scouted ahead and covered the flanks of marching regiments. Serving among men chosen for their build made her disguise more convincing.
Q 20Near which Hudson Valley town in New York was Deborah Sampson wounded in a 1782 skirmish?
Tarrytown
Tarrytown is where about 30 infantrymen from her unit ran into a fight in the summer of 1782. She begged her comrades not to take her to a doctor, fearing discovery.
John Paterson learned her secret from a doctor's note that she delivered to him herself. Instead of a reprimand, he gave her a discharge, some words of advice and money to get home.
Q 24Which doctor found out Deborah Sampson was a woman, kept quiet, and nursed her in his own home?
Barnabas Binney
Barnabas Binney had his wife, his daughters and a nurse look after her, and told the Army nothing. He later sent her to her general carrying a note that revealed the truth.
Q 25At which New York post on the Hudson River was Deborah Sampson honorably discharged in 1783?
West Point
West Point saw her leave the Army with an honorable record after a year and a half in uniform. Other women caught serving as men had been reprimanded.
Q 26Which general, a former Boston bookseller, gave Deborah Sampson her honorable discharge in 1783?
Henry Knox
Henry Knox, the artillery chief who hauled captured cannon from Ticonderoga to Boston, signed her out of the Army. She had served a year and a half without being found out by her officers.
Q 27In which Massachusetts town did Deborah Sampson spend her married life on the Gannett family farm?
Sharon
Sharon still has the Deborah Sampson Gannett House, though it is privately owned and closed to visitors. The farmland around it is protected from development.
Q 28Which Massachusetts governor signed the 1792 act granting Deborah Sampson her withheld Army pay?
John Hancock
John Hancock approved 34 pounds plus interest, pay the Army had held back because she was a woman. She had petitioned the state legislature for it that January.
Q 29Herman Mann's 1797 biography of Deborah Sampson was published under which title?
The Female Review
The Female Review came out while she was still alive, written by a man who knew her personally for years. The other three titles are modern books about her life.
Q 30The Deborah Sampson Act, passed by Congress in 2020, removes barriers to care for which group?
Women veterans
Women veterans gained a dedicated Office of Women's Health under the law. It carries the name of a woman who spent years petitioning to be paid for her own service.