William Penn
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50 free William Penn trivia questions with answers — history quiz, new questions added Oct 2026.
William Penn established Pennsylvania in 1681, but the road there ran through expulsion, family rows and more than one jail cell. Few colonial founders make better trivia: he was a rich man's son who chose a persecuted faith, argued with judges, and still talked a king into handing him one of the largest grants in colonial history. This quiz covers the whole story: his youth and conversion, the trials that made legal history, the founding and planning of his colony, his dealings with Native Americans, and the statues, legends and brand names that keep his memory alive. Every answer comes with a short explanation, so the fun facts stick. It suits students of colonial America, Pennsylvania locals, trivia-night hosts and anyone curious about the man behind the name. Questions go from easy openers to a few deep cuts for history buffs.
30 of 50 questions with answers and explanations. Play the quiz
Q 01For roughly how long did William Penn actually live in Pennsylvania, the colony he founded?
About 4 years
About 4 years is all William Penn spent in America, split across two visits in 1682–84 and 1699–1701. Money troubles and court politics kept pulling him back across the Atlantic, and he never returned after 1701.
Q 02After 1909, one cereal company's advertising named William Penn as the man pictured on its boxes of what?
Oats
Quaker Oats advertising called its logo figure William Penn, the standard bearer of the Quakers. The company has since said the man on the box does not depict Penn.
Q 03Which childhood disease cost William Penn his hair, leaving him to wear wigs for most of his life?
Smallpox
Smallpox struck William Penn as a small boy and took his hair with it. The illness also prompted his parents to move the family out to a country estate in Essex, where he picked up a lifelong love of gardening.
Q 04At his 1670 trial for street preaching, William Penn was jailed for contempt after refusing to remove what?
His hat
His hat stayed on because Quakers would not bare their heads to social superiors, holding that all men were equal under God. The gesture sent Penn to Newgate jail.
Q 05The most authentic portrait of the pacifist Quaker William Penn shows him at 22 dressed in what?
A suit of armor
A suit of armor appears in the 1666 portrait, painted after Penn helped put down a rebellion as a young soldier. Soon afterward he joined a faith that renounces the use of force.
Q 06The Curse of Billy Penn, begun when a tower outgrew William Penn's statue, ended with a 2008 title in which sport?
Baseball
Baseball's Phillies won the 2008 World Series a year after builders fixed a tiny Penn statuette to the top beam of the city's new tallest skyscraper. No major Philadelphia team had won a title since 1983.
Q 07Which Philadelphia icon's inscription may mark the 50th anniversary of William Penn's Charter of Privileges?
The Liberty Bell
The Liberty Bell carries a Bible verse about proclaiming liberty, picked by Assembly speaker Isaac Norris in 1751. Penn's 1701 charter had promised Pennsylvanians religious freedom and a real say in their own government.
Q 08The University of Pennsylvania was founded not by William Penn but by which later Philadelphian?
Benjamin Franklin
Benjamin Franklin founded the academy that grew into the University of Pennsylvania, decades after William Penn died in 1718. The school's short name comes from the state, not from the man.
Q 09Pennsylvania's name honors not William Penn but his father, a man celebrated in which profession?
Admiral
Admiral Sir William Penn had helped bring the monarchy back in 1660, and the King insisted on honoring him. The younger Penn had proposed plain Sylvania; the King added the family name himself.
Q 10William Penn named his capital city Philadelphia, a name built from Greek words with which meaning?
Brotherly love
Brotherly love is what the Greek roots phílos and adelphós add up to. Penn, who had been jailed for his beliefs, wanted a town where nobody would be persecuted for theirs.
Q 11Which king granted William Penn the charter for Pennsylvania in 1681, clearing money the Crown owed his family?
Charles II
Charles II signed the charter on 4 March 1681, cancelling about £16,000 the Crown owed the Penn family. In return the King was promised a fifth of any gold and silver mined there, of which there was almost none.
Q 12With which Native American people did William Penn make his land purchases and his famous treaty of peace?
Lenape
The Lenape sold land to William Penn while keeping the right to travel over it to hunt, fish and gather. Penn insisted on paying for territory the King had already handed him on paper.
Q 13A 37-foot bronze statue of William Penn has stood since 1894 on top of which Philadelphia building?
City Hall
Q 21The colony name Pennsylvania joins William Penn's family surname to a Latin word meaning what?
Woods
Woods, or forests, is the meaning of the Latin Sylvania, so the name reads as Penn's Woods. The royal charter handed Penn more than 45,000 square miles of them.
Q 22Which name did William Penn first propose for his colony, before Sylvania and long before Pennsylvania?
New Wales
New Wales was William Penn's first choice, dropped for Sylvania before the King had the final say. Welsh settlers came anyway, among the many persecuted minorities drawn by his prospectus.
Q 23Which founder of the Quaker movement became William Penn's close ally and travelling companion across Europe?
George Fox
City Hall carries the largest statue on top of any building in the world, hoisted up in fourteen sections. Its sculptor was annoyed that Penn was set facing northeast rather than south into the sun.
Q 14William Penn was expelled in 1662 from which university after rebelling against compulsory chapel?
Oxford
Oxford expelled William Penn for religious nonconformity, and his furious father beat him with a cane and turned him out of the house. His old college, Christ Church, displays his portrait in its dining hall.
Q 15After publishing The Sandy Foundation Shaken in 1668, William Penn spent eight months in solitary confinement where?
Tower of London
The Tower of London held William Penn in an unheated cell while the Bishop of London waited for him to recant. Handed paper to write a retraction, he wrote another defiant book instead.
Q 16Which name did William Penn give his plan to run Pennsylvania on Quaker ideals of peace and tolerance?
Holy Experiment
Holy Experiment was Penn's term for a colony offering religious freedom to Quakers and other persecuted minorities. For all his sincerity, he also expected the venture to make him rich, and it never did.
Q 17William Penn wanted a spacious country town and so had Philadelphia's streets laid out in which pattern?
A grid
A grid of wide, straight streets kept houses far apart, with five public squares left open as parkland. The cramped capital he grew up in had been ravaged by plague and the Great Fire in the 1660s.
Q 18William Penn's plan for Philadelphia crossed its numbered streets with streets named after what?
Trees
Trees gave their names to Chestnut, Walnut and Mulberry Streets, laid east to west across the numbered ones. Mulberry has since been renamed Arch Street, but most of the others survive.
Q 19Which present-day US state began as the three Lower Counties of William Penn's Pennsylvania?
Delaware
Delaware's three counties won their own assembly in 1701 after years of clashes with Penn's government in Philadelphia. They still shared a governor with Pennsylvania until 1776.
Q 20Which famous surveyed boundary finally settled the feud William Penn began with Lord Baltimore?
Mason–Dixon line
The Mason–Dixon line was surveyed in the 1760s for the Penn and Calvert heirs, ending some eighty years of dispute. Penn had never checked where his charter's southern boundary, the 40th parallel, actually ran.
George Fox began the movement in the 1650s, and William Penn became its first theologian and legal defender. Penn later wrote the introduction to Fox's published journal.
Q 24William Penn's fellow Quakers belong to a faith formally known by which name?
Society of Friends
Society of Friends is the formal name; outsiders coined 'Quakers' after the movement's founder told a judge to quake before the authority of God. In Penn's day they worshipped in silence, with no clergy.
Q 25Which book did William Penn write behind bars in 1668–69, citing 68 authors from memory?
No Cross, No Crown
No Cross, No Crown was supposed to be a retraction: Penn's jailers gave him paper hoping he would recant. Instead he wrote a call to self-denial that became a classic of Christian literature.
Q 26William Penn's laws for Pennsylvania kept the death penalty for only two crimes: treason and which other?
Murder
Murder and treason alone carried death in Penn's code, at a time when English law listed some two hundred capital crimes. His jails were meant to reform inmates through work in workshops.
Q 27William Penn himself presided over the trial of Margaret Mattson, a Swedish-Finnish settler accused of what?
Witchcraft
Witchcraft was the charge, brought by neighbors who claimed Mattson had bewitched their cattle. She was found guilty only of having the reputation of a witch, not of being one, and was released.
Q 28Tradition says William Penn made his treaty of friendship at Shackamaxon in the shade of a great what?
Elm
The Treaty Elm stood on the riverbank until a storm blew it down in 1810. The spot is now Penn Treaty Park, where a descendant of the original was planted in 2010.
Q 29Which Pennsylvania-born artist painted the famous scene of William Penn's treaty for Penn's son Thomas?
Benjamin West
Benjamin West, born into a Quaker family near Philadelphia, painted it in England nearly ninety years after the event. He put brick buildings in the background that did not exist in 1682.
Q 30After strokes disabled William Penn in 1712, who ran Pennsylvania's affairs until 1726?
His wife Hannah
His wife Hannah acted as proprietor from 1712 until her death in 1726, beating a lawsuit from Penn's eldest son along the way. She was later the first woman named an honorary US citizen.