Dolley Madison
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40 free Dolley Madison trivia questions with answers — history quiz, new questions added Oct 2026.
Dolley Madison turned the job of president's wife into a public role. She charmed friends and rivals alike, set fashions, stood her ground as enemy troops marched on the capital, and stayed the most admired woman in Washington for decades after her husband left office. This quiz covers the fun facts people look for: her childhood and family, her first marriage and early loss, how she met James Madison, her famous receptions, the night the White House burned, and the honors, hardships and legends of her later years. It suits students, teachers building a lesson on first ladies or the early republic, and anyone who enjoys a good life story. Every answer comes with a short explanation, so you pick up the history as you play.
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Q 01Which artist painted the George Washington portrait that Dolley Madison refused to abandon in 1814?
Gilbert Stuart
Gilbert Stuart's canvas was screwed to the wall, so she had the frame broken and the picture carried off by two New Yorkers. It hangs in the White House again today.
Q 02Which inventor asked Dolley Madison in 1844 to send the first personal message over his new line to Baltimore?
Samuel Morse
Samuel Morse had just demonstrated his telegraph in the Capitol when he turned to her for a message of her own. She sent her love to a friend in Baltimore.
Q 03Dolley Madison's elder son, John Payne Todd, was born in 1792 on which notable day of the calendar?
Leap Day
Leap Day, February 29, gave him a true birthday only once every four years. Known as Payne, he was two when his mother married James Madison.
Q 04Which New York senator, an old college friend of James Madison, introduced him to the widowed Dolley Todd in 1794?
Aaron Burr
Aaron Burr had boarded at her mother's house, and that spring she named him guardian of her small son in her will. The couple married four months after the introduction.
Q 05Which pet did Dolley Madison send to the French consulate for safekeeping as she fled the capital in 1814?
A parrot
A parrot named Polly, a macaw that spoke French, was a favorite family pet. Her niece later wrote that a night hawk killed the bird when it was left off its perch one night.
Q 06Dolly Madison snack cakes, named after Dolley Madison, were long advertised by characters from which comic strip?
Peanuts
Peanuts characters appeared on the packages and in TV commercials from the 1960s into the 1980s. The brand, started in 1937, dropped the 'e' from her first name.
Q 07Which religious group expelled Dolley Madison in 1794 for marrying James Madison, who was not a member?
The Quakers
The Quakers had raised her in plain dress under strict rules. Once read out of meeting, she began attending Episcopal services and took up the latest city fashions.
Q 08What struck Washington within a day of British troops burning the White House that Dolley Madison had fled?
A violent storm
A violent storm, complete with a tornado that tossed cannons, put out the fires. It became known as the storm that saved the city, though it wrecked more buildings too.
Q 09Which disease killed Dolley Madison's first husband, John Todd, and their baby son during a 1793 epidemic?
Yellow fever
Yellow fever also took both of her in-laws that autumn. At 25 she was left a widow with one surviving son, and had to sue her brother-in-law for her inheritance.
Q 10Dolley Madison sometimes stepped in as White House hostess for which widowed president, a close friend of her husband?
Thomas Jefferson
Thomas Jefferson usually relied on his daughters, so she filled in only when they were away. Her own house on F Street became the capital's real social hub.
Q 11British troops forced Dolley Madison to flee the White House during which conflict, later ended by the Treaty of Ghent?
The War of 1812
The War of 1812 reached her door in August 1814. Her husband approved the peace treaty the following winter in a private house nearby, the mansion being a burned-out shell.
Q 12Which exotic style of headwear became Dolley Madison's fashion trademark, worn with the high-waisted gowns of her day?
A turban
A turban was her calling card for decades. She was still wearing a white one when she sat for photographs in her last years, long after the style had passed.
Q 13Dolley Madison's family moved when she was 15 to which city, where she later met James Madison?
Philadelphia
Q 21Which man enslaved by Dolley Madison's family later published the first memoir of life in the White House?
Paul Jennings
Paul Jennings was about 15 during the 1814 evacuation. His 1865 book says servants, not the first lady herself, took the famous portrait off the wall.
Q 22Which famous senator often sent market baskets of food to the impoverished Dolley Madison in her last years?
Daniel Webster
Daniel Webster sent the market baskets after learning how short of money she was. Her son's gambling debts had swallowed the family fortune.
Q 23Dolley Madison bonded with the War Hawk congressman Henry Clay by sharing which tobacco habit with him?
Taking snuff
Philadelphia became the national capital in 1790, which is how a Virginia congressman came to be living in the same city as the young widow.
Q 14James Madison held which cabinet post from 1801 to 1809, the years Dolley Madison became the capital's leading hostess?
Secretary of State
Secretary of State was the senior cabinet seat, which put his wife first in rank among the capital's hostesses for eight years before she ever lived in the White House.
Q 15Legend credits Dolley Madison with starting which annual White House tradition for children, supposedly in 1814?
The Easter Egg Roll
The Easter Egg Roll is on firmer ground from 1878, when Rutherford and Lucy Hayes welcomed children who had just been banned from rolling eggs on the Capitol lawn.
Q 16Dolley Madison hosted which Washington first at Long's Hotel in March 1809, with 400 tickets sold at $4 each?
An inaugural ball
An inaugural ball had been thrown for George Washington in New York in 1789, but hers was the first in the new federal city, held the evening her husband was sworn in.
Q 17Which Virginia plantation, the Madison family home, did the widowed Dolley Madison sell in 1844 to pay debts?
Montpelier
Montpelier passed to a new owner that August. She wrote that no one could appreciate her grief and dismay at handing a beloved home to someone else.
Q 18Dolley Madison liked to call herself a Virginian but was actually born in a log cabin in which present-day state?
North Carolina
North Carolina was home for less than a year. Her parents had joined the New Garden settlement, now part of Greensboro, and were back in Virginia by early 1769.
Q 19Dolley Madison raised money for the Washington Monument alongside the elderly widow of which Founding Father?
Alexander Hamilton
Alexander Hamilton's widow, Eliza, was by then in her nineties. She, Dolley Madison and Louisa Adams lent their famous names to the fundraising drive.
Q 20Dolley Madison escaped unharmed in 1844 when a giant cannon burst aboard a Navy warship carrying which president?
John Tyler
John Tyler was below decks when the gun called the Peacemaker blew apart on the Potomac, killing two members of his cabinet and four other people.
Taking snuff together gave her a way to reach a man her husband could not approach directly. A friend said her little box had a magic influence.
Q 24After the 1814 invasion, Dolley Madison became first directress of a Washington society that cared for which group?
Orphans
Orphans became her cause once the fighting ended: she gave time and money and urged other women to join. It made her the first president's wife tied to a public charity.
Q 25What did the widowed Dolley Madison sell to Congress in two lots, in 1837 and 1848, to ease her debts?
Her husband's papers
Her husband's papers included his own notes on the 1787 convention. The second payment was placed in a trust so her spendthrift son could not get at it.
Q 26The earliest known photograph of any U.S. first lady shows Dolley Madison around 1846 in which early process?
Daguerreotype
Daguerreotype was the process, and the sitter was nearly 80. The National Portrait Gallery acquired the picture in 2024.
Q 27Which Hollywood star played Dolley Madison opposite Burgess Meredith's James Madison in the 1946 film Magnificent Doll?
Ginger Rogers
Ginger Rogers took the role in a drama that invents a love triangle with a scheming rival suitor. RC Cola ran ads showing her in costume as the first lady.
Q 28Which famous group was introduced to the press in 1959 at Dolley Madison's former home in Washington?
The Mercury Seven
The Mercury Seven astronauts faced reporters there because NASA was using the yellow house at the time. It is now occupied by a federal appeals court.
Q 29Dolley Madison's sister Lucy married a man holding which office at the first White House wedding, in 1812?
Supreme Court justice
Supreme Court justice Thomas Todd of Kentucky was the groom. The bride was the widow of a nephew of George Washington.
Q 30After the White House burned, Dolley Madison and her husband lived for six months in which Washington mansion?
The Octagon
The Octagon belonged to John Tayloe, a Federalist with little love for the war. The Madisons paid $500 in rent, and the peace treaty was approved in its upstairs study.