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50 free James Monroe trivia questions with answers — history quiz, new questions added Aug 2026.
James Monroe was the last Founding Father to reach the White House and the last president to wear a powdered wig and knee-breeches, which is why contemporaries called him the Last Cocked Hat. He was wounded at Trenton, shared a log hut at Valley Forge with John Marshall, studied law under Thomas Jefferson, and later fell out with James Madison before serving as his Secretary of State and Secretary of War at the same time. His presidency gave the country the Era of Good Feelings, the Missouri Compromise, the acquisition of Florida, the 49th-parallel border with Canada and the doctrine that still carries his name. He died on July 4, 1831, the third president to go on Independence Day, and Liberia's capital is named for him. These 50 questions move from the basics to the details only serious presidential buffs know: the elector who spoiled his unanimous 1820 vote, his pseudonym, his abandoned book and the price he was actually authorised to pay for New Orleans.
30 of 50 questions with answers and explanations. Play the quiz
Q 01Which number president of the United States was James Monroe?
5th
Monroe followed Madison and was the last of the so-called Virginia dynasty of presidents.
Q 02Monroe's presidency coincided with which famously named political period?
Era of Good Feelings
The phrase was coined around his 1817 inauguration, the first to come during general peace and economic stability.
Q 03Which political party did Monroe belong to?
Democratic-Republican
He became one of the fledgling party's leaders in the Senate in the early 1790s.
Q 04Monroe studied law from 1780 to 1783 under which future president?
Thomas Jefferson
Jefferson opened his library to his protégé, where the works of Epictetus made a lasting impression.
Q 05Monrovia, a national capital named after Monroe, is the capital of which country?
Liberia
It is the only national capital besides Washington, D.C. named after a U.S. president.
Q 06In which Virginia county was Monroe born in 1758?
Westmoreland
The birthplace sits a mile from the community now known as Monroe Hall, and the site joined the National Register in 1979.
Q 07Monroe suffered a severed artery and nearly died in which 1776 engagement?
Battle of Trenton
Washington cited him for bravery after the surprise attack on the Hessian camp and promoted him to captain.
Q 08Monroe shared a log hut at Valley Forge in 1777–78 with which future chief justice?
John Marshall
The two had been classmates at Campbelltown Academy, the only school in their county.
Q 09Which painter's 1851 canvas memorialised Monroe's part in the 1776 river crossing?
Emanuel Leutze
Trumbull painted Monroe too, in his canvas of the Hessians' capture at Trenton.
Q 10As Jefferson's special envoy, Monroe helped negotiate which 1803 land deal?
Louisiana Purchase
The deal nearly doubled the size of the United States.
Q 11How much did Monroe and Livingston agree to pay France for all of Louisiana?
$15 million
Monroe violated his instructions to close the deal, and Jefferson backed him anyway.
Q 12Monroe's instructions in 1803 had authorised how much for New Orleans and West Florida?
$9 million
He ended up spending far more than authorised, but on a far bigger prize.
Q 13Who was Monroe's Federalist opponent in the 1816 presidential election?
Rufus King
The Federalists offered little resistance after opposing a war the public regarded as a victory.
Q 21Under the 1819 treaty with Spain, the US assumed citizens' claims up to what sum?
$5 million
In return the United States renounced its claims to Texas and the lands west of the new line.
Q 22On what date did Monroe deliver the annual message that became the Monroe Doctrine?
December 2, 1823
It began by restating neutrality toward European wars before warning against recolonisation.
Q 23The Monroe Doctrine's line against new colonisation was aimed primarily at which power?
Russia
St Petersburg had closed the Pacific coast north of 51° to foreign ships in 1821.
Q 14How many of the 217 electoral votes did Monroe win in 1816?
183
He lost only Massachusetts, Connecticut and Delaware.
Q 15Which New Hampshire elector denied Monroe a unanimous Electoral College in 1820?
William Plumer
The tale that he did it to preserve Washington's unique honour came later; he simply thought Monroe incompetent.
Q 16Who served as vice president for both of Monroe's terms?
Daniel D. Tompkins
He was the only 19th-century vice president to serve two full terms.
Q 17Which Massachusetts man did Monroe choose as his Secretary of State?
John Quincy Adams
The choice acknowledged Northern discontent with the Virginia dynasty and made him the early favourite to succeed Monroe.
Q 18Which South Carolina congressman became Monroe's Secretary of War?
John C. Calhoun
Monroe turned to him only after Andrew Jackson declined the post.
Q 19Which general seized the Spanish capital of Pensacola during Monroe's 1818 Seminole campaign?
Andrew Jackson
Many in Congress called it an undeclared war, but Monroe and Adams defended him.
Q 20Which Spanish ambassador co-signed the 1819 treaty ceding the Floridas?
Luis de Onís
The treaty also drew a border from the Sabine River all the way to the Pacific along the 42nd parallel.
Q 24Which British foreign secretary sought a joint Anglo-American statement in 1823?
George Canning
Adams argued against a bilateral statement, and two months later it became a unilateral American declaration.
Q 25Which 1817 agreement with Britain regulated naval armaments on the Great Lakes?
Rush–Bagot Treaty
It helped avoid an expensive naval arms race on the lakes.
Q 26The Treaty of 1818 fixed the border from Minnesota to the Rockies along which parallel?
49th
The same accords set up a joint occupation of Oregon Country for ten years.
Q 27The 1824 treaty with the Tsar set the southern limit of his Pacific claims at which line?
54°40′
That line is the present southern tip of the Alaska Panhandle.
Q 28Monroe signed the Missouri Compromise into law in which year?
1820
He opposed any limit on slavery's expansion but signed it as the least bad option for southern slaveholders.
Q 29The Missouri Compromise excluded slavery from Louisiana Territory north of which line?
36°30′
The line is the southern boundary of Missouri itself, which was exempted.
Q 30Which New York congressman's 1819 amendment touched off the Missouri crisis?
James Tallmadge Jr.
His amendment would have freed children of enslaved parents in Missouri at age 25.