Underground Railroad
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50 free Underground Railroad trivia questions with answers — history quiz, new questions added Oct 2026.
The Underground Railroad ran on nerve, not steam. In the decades before the Civil War, enslaved people walked, rode and sailed out of the South with help from a loose network of Black and white allies, and tens of thousands reached free soil. Their stories include some of the boldest escapes in American history. This quiz covers the whole story: Harriet Tubman's life and missions, the code words borrowed from the railways, famous escapes and the people who planned them, the laws and court cases that followed fugitives into the free states, and the places in Canada where many journeys ended. A few questions look at how novels, film and television have retold it. The questions suit classrooms, Black History Month quiz nights and anyone who wants to test what they remember from school. Every answer comes with a short explanation, so you learn something even when you miss.
30 of 50 questions with answers and explanations. Play the quiz
Q 01Which enslaved Virginian escaped by having himself shipped to Philadelphia abolitionists inside a wooden crate?
Henry Brown
Henry Brown spent 27 hours in a box labelled as dry goods, carried by wagon, railroad and steamboat. He later toured England as a magician under the nickname Box.
Q 02Harriet Tubman's rescue missions into slave territory earned her the name of which biblical prophet?
Moses
Moses led the Hebrews out of Egypt, and Tubman made some 13 trips back south to bring about 70 relatives and friends out of slavery.
Q 03Frederick Douglass escaped Baltimore by train in 1838 wearing the uniform of which profession?
A sailor
A sailor's uniform and a free seaman's papers carried Douglass to New York in under 24 hours. His future wife, Anna Murray, supplied the clothes and part of her savings.
Q 04Which pattern in the night sky did freedom seekers call the drinking gourd and use to find north?
The Big Dipper
The Big Dipper gave its nickname to the folk song Follow the Drinking Gourd, though scholars doubt that such songs carried real directions for people on the run.
Q 05Harriet Tubman often began escapes on which evening, since runaway notices could not be printed until Monday?
Saturday
Saturday starts bought her groups a head start, and she usually worked in winter, when long nights and cold weather kept people indoors.
Q 06What did the name Underground Railroad describe in the decades before the Civil War?
Secret routes and safe houses
Secret routes and safe houses were described in the slang of the newest transport of the day. The first railway that really ran underground did not open until 1863.
Q 07In Underground Railroad slang, what name was given to guides who led freedom seekers between hiding places?
Conductors
Conductors included free-born Black Americans, white abolitionists, formerly enslaved people and Native Americans. Some posed as enslaved workers to get onto a plantation.
Q 08Since the 1980s, a disputed theory has held that patterns on which household items guided freedom seekers north?
Quilts
Quilts hung one at a time on a fence were said to carry ten coded patterns, but historians have found no evidence from the period that such a code existed.
Q 09A southern branch of the Underground Railroad led to which country, which abolished slavery in 1829?
Mexico
Mexico ended slavery under President Vicente Guerrero, who was himself of African descent, and people who crossed its border from the United States became free.
Q 10Ona Judge fled the President's House in Philadelphia by ship, escaping enslavement by which president's family?
George Washington
George Washington's household was packing for a trip to Virginia when Judge slipped away. She reached New Hampshire and was never recaptured, though in law she stayed a fugitive for life.
Q 11Freedom seekers gave the Ohio River, the border between slave and free states, the name of which biblical river?
Jordan
Jordan was the river the Israelites crossed to enter the Promised Land, which is the name fugitives gave to Canada.
Q 12Harriet Tubman was born into slavery in Dorchester County, on the Eastern Shore of which state?
Maryland
Maryland bordered free Pennsylvania, and Tubman escaped to Philadelphia in 1849, only to go back soon afterwards to rescue her family.
Q 13Which novelist turned a true tale of a mother carrying her child across Ohio River ice into fiction?
Harriet Beecher Stowe
Harriet Beecher Stowe heard the tale from the minister John Rankin, who had housed the woman in 1838, and modelled Eliza in Uncle Tom's Cabin on her.
Q 21Many freedom seekers finished the journey to Canada by boat from Ohio ports across which body of water?
Lake Erie
Lake Erie lay at the end of the main route north, which ran up the Appalachians and through the strongly anti-slavery Western Reserve of northeastern Ohio.
Q 22In 1978 Harriet Tubman became the first African-American woman to be honoured on which everyday item?
A postage stamp
A postage stamp carried her portrait again in 1995, when the United States issued a second Tubman design.
Q 23Which novelist won the 2017 Pulitzer Prize for a book that imagines the Underground Railroad as real trains in tunnels?
Colson Whitehead
Q 14Which actress earned an Academy Award nomination for playing Harriet Tubman in the 2019 film Harriet?
Cynthia Erivo
Cynthia Erivo was nominated twice over for the film: she also co-wrote its song Stand Up, which was up for the Oscar, Grammy and Golden Globe.
Q 15Which constitutional amendment of December 1865 made the Underground Railroad unnecessary by outlawing slavery?
The Thirteenth
The Thirteenth Amendment kept one exception in its text: slavery and involuntary servitude were banned except as punishment for a crime.
Q 16Which Christian group, the faith of Pennsylvania founder William Penn, was especially active in hiding freedom seekers?
Quakers
Quakers had not always opposed slavery: in colonial Pennsylvania it was fairly common for Friends to own slaves, until protests from their own members turned the group against it.
Q 17As an adolescent, Harriet Tubman suffered a lifelong head injury when an overseer threw which object at another person?
A metal weight
A metal weight of about two pounds, aimed at a man who had left work without permission, hit her instead. The wound brought seizures and vivid visions that she took as messages from God.
Q 18Harriet Tubman helped a militant abolitionist plan and recruit for his 1859 raid on which Virginia town?
Harpers Ferry
Harpers Ferry was attacked on October 16, 1859, but Tubman, whom the raid's leader called General Tubman, was in New York City when it happened.
Q 19Most freedom seekers who reached Canada settled in which present-day province, then known as Canada West?
Ontario
Ontario drew the largest group, and whole villages of formerly enslaved people grew up in its Kent and Essex counties.
Q 20The 1856 escape of Margaret Garner across the frozen Ohio River inspired which Toni Morrison novel?
Beloved
Beloved grew out of what Garner did when slave catchers cornered her family: she killed her two-year-old daughter rather than see the child returned to slavery.
Colson Whitehead won the fiction Pulitzer a second time in 2020 for The Nickel Boys, a double that very few writers have managed.
Q 24Which surveyed boundary on Pennsylvania's southern edge became shorthand for the divide between free and slave states?
The Mason–Dixon Line
The Mason–Dixon Line was surveyed in the 1760s to end a quarrel between colonies, and took on its later meaning once Pennsylvania had abolished slavery.
Q 25Harriet Tubman carried which weapon on her missions as protection against slave catchers and their dogs?
A revolver
A revolver also kept her groups moving: when one man lost his nerve and wanted to go back, she aimed it at his head and gave him the choice of walking on or dying.
Q 26Which Philadelphia abolitionist kept hidden notes on hundreds of escapes and published them as a book in 1872?
William Still
William Still interviewed every arrival, and one man he questioned turned out to be his own brother Peter, whom he had never met.
Q 27Which Indiana merchant, said to have sheltered 3,000 fugitives, was nicknamed President of the Underground Railroad?
Levi Coffin
Levi Coffin was first given the title by an exasperated slave catcher, and his house in Fountain City became known as the network's Grand Central Station.
Q 28Which woman escaped slavery in 1848 disguised as a white male planter, with her husband posing as her servant?
Ellen Craft
Ellen Craft and her husband William rode first-class trains and steamboats from Macon to Philadelphia, arriving on Christmas Day.
Q 29After the 1851 Christiana Resistance in Pennsylvania, 41 people were indicted for which crime against the United States?
Treason
Treason proved impossible to make stick: a jury took only 15 minutes to acquit the first defendant, and the charges against everyone else were dropped.
Q 30Frederick Douglass named his Rochester abolitionist newspaper after which nighttime guide followed by freedom seekers?
The North Star
The North Star first appeared in December 1847, paid for with money English supporters had given Douglass, and it figuratively stood for Canada as well.