130 free Boston trivia questions with answers — geography quiz, new questions added Aug 2026.
56 free Boston trivia questions with answers. This trivia about Boston runs from the Puritans landing on the Shawmut Peninsula in 1630 to the Big Dig and the Celtics' eighteenth banner. In between are the Tea Party and the Massacre, Paul Revere's lanterns, the oldest subway in North America, the day a wave of molasses tore through the North End, and the night two fake policemen walked out of the Gardner Museum with a Vermeer. It is written for Bostonians who want to test their local pride, visitors planning a walk along the Freedom Trail, teachers building a unit on the American Revolution, and pub quiz hosts who need a city round. The mix leans easy to medium, with a handful of tough ones on dates, architects and the State House dome. Every answer has been checked against city histories and encyclopaedic sources, so you can repeat them on the Swan Boats without fear of correction.
30 of 130 questions with answers and explanations. Play the quiz
Q 01Boston was named after a market town in which English county?
Lincolnshire
Puritan settlers founded it on a near-empty peninsula in 1630.
Q 02In what year was Boston founded?
1630
Settlers led by John Winthrop crossed over from the failing colony at Charlestown.
Q 03Boston Common, dating from 1634, holds what national distinction?
The first public park in the U.S.
The city also claims the first public school (1635) and the first subway (1897).
Q 04Founded in 1635, which institution is the oldest public high school in the United States?
Boston Latin
Benjamin Franklin attended it but never graduated.
Q 05The oldest subway tunnel in North America, opened in Boston in 1897, runs beneath which thoroughfare?
Tremont
Only London's 1890 tube and Budapest's 1896 line are older among electric subways still in use.
Q 06What did settler William Blaxton call the peninsula on which Boston stands?
Shawmut
The Puritans he invited over from Charlestown called it Tremontaine, after its three hills.
Q 07Boston's Back Bay neighbourhood was created in the 19th century by doing what?
Filling in tidal marshland
Nearly 600 acres of Charles River marsh were filled with gravel brought by rail from Needham.
Q 08On which date did the Boston Tea Party take place?
December 16, 1773
Sons of Liberty disguised as Native Americans dumped about 342 chests of East India Company tea.
Q 09Roughly how many chests of tea were thrown into Boston Harbor at the Tea Party?
342
The Tea Act had authorised 5,000 chests, about 250 tons, for the American colonies.
Q 10How many colonists were killed in the Boston Massacre of March 1770?
Five
Crispus Attucks, a mixed-race former slave, was among the first to die.
Q 11Which future U.S. president defended the British soldiers accused in the Boston Massacre?
John Adams
His cousin Samuel was one of the leading agitators on the other side.
Q 12The June 1775 battle everyone calls Bunker was mostly fought on which rise in Charlestown?
Breed's Hill
The British took the ground on June 17, 1775, but at a cost so heavy it was a pyrrhic victory.
Q 13The granite obelisk in Charlestown commemorating the June 1775 battle stands how tall?
221 feet
Dedicated in 1843, it was then the largest obelisk in the United States.
Q 21Who designed the Massachusetts State House, completed in 1798 on Beacon Hill?
Charles Bulfinch
Paul Revere's company sheathed its leaking wooden dome in copper in 1802; the gold leaf came in 1874.
Q 22The State House dome was first gilded with gold leaf in which year?
1874
It had earlier been painted grey and then light yellow; the 1997 regilding used 23-karat gold.
Q 23A wave of what substance killed 21 people in Boston's North End on January 15, 1919?
Molasses
The 2.3-million-gallon tank burst and the wave moved at an estimated 35 mph; locals swore the smell lingered for decades.
Q 14Two lanterns in which Boston landmark's steeple signalled the British advance in 1775?
Old North Church
Built in 1723, it is the oldest standing church in the city.
Q 15What was Paul Revere's trade?
Silversmith
In 1800 he became the first American to roll copper into sheets, later used to sheathe naval hulls.
Q 16Which Founding Father was born on Boston's Milk Street in 1706?
Benjamin Franklin
He was his father's fifteenth child and was baptised at the Old South Meeting House.
Q 17The USS Constitution, berthed in Charlestown, earned what nickname after defeating HMS Guerriere in 1812?
Old Ironsides
Launched in 1797, she is the oldest naval vessel in the world still afloat.
Q 18Faneuil Hall, nicknamed the Cradle of Liberty, is topped by a weathervane in the shape of what?
A grasshopper
The building opened in 1742 as a marketplace and meeting hall.
Q 19The Freedom Trail through Boston is marked on the pavement by what?
A red line of bricks
The 2.5-mile route was conceived by journalist William Schofield in 1951 and links 16 sites.
Q 20How long is the Freedom Trail?
About 2.5 miles
Most sites are free, though the Old State House and Paul Revere House charge admission.
Q 24First run in 1897, what record does the Boston Marathon hold?
World's oldest annual one
It was inspired by the marathon at the first modern Olympics in Athens the previous year.
Q 25The Boston Marathon starts in which town?
Hopkinton
It finishes on Boylston Street near Copley Square, and is run on Patriots' Day.
Q 26The Boston Marathon is traditionally run on which holiday?
Patriots' Day
That is the third Monday of April, when the Red Sox also play a morning home game.
Q 27In what year did women officially become eligible to enter the Boston Marathon?
1972
Organisers now recognise 1966, when Bobbi Gibb ran unofficially, as the first women's finish.
Q 28Fenway Park opened in 1912; what news story overshadowed coverage of its first game?
The sinking of the Titanic
The Titanic had gone down five days earlier, on April 15.
Q 29How tall is Fenway Park's Green Monster wall in left field?
37 feet
It replaced Duffy's Cliff and the original 25-foot wall during the 1934 rebuild.
Q 30The illuminated Citgo sign that looms over Fenway Park overlooks which part of the city?
Kenmore Square
Installed in 1940, it got Citgo's current logo in 1965 and became famous on Red Sox broadcasts.