These Boston trivia questions cover one city across four centuries in five rounds: founding and colonial Boston, Boston in the Revolution, Boston firsts, the shape of the city, and landmarks, food and words.
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Five rounds across four centuries
Founding and colonial Boston starts in 1630 on the Shawmut Peninsula. Boston in the Revolution covers the two lanterns, Dorchester Heights and the Freedom Trail. Boston firsts has the oldest city park, the first lighthouse and the oldest subway tunnel in North America. The shape of the city explains the Back Bay, the Emerald Necklace and the Big Dig. Landmarks, food and words ends with the Sacred Cod and baked beans.
Quiz a table or yourself
Tap a choice to check it; the reason and the page it was read on appear with the answer. Scored round asks 20 before it marks any. Team scores go on paper.
Tips
No sports round: no team, league or player is an answer anywhere in this pack.
Questions and answers
What are some easy Boston trivia questions?
In which year was Boston founded? How many lanterns were lit in Old North Church on April 18, 1775? What sweetens Boston baked beans? The answers are 1630, two and molasses.
What is Boston known for being first at?
Boston Common is the oldest city park in the United States, Boston Light of 1716 was the first lighthouse in what is now the United States, and the Tremont Street subway is the oldest subway tunnel in North America.
What is the Freedom Trail?
A 2.5-mile path through Boston that passes 16 places that matter to the history of the United States.
How were the answers checked?
Each was read on October 3, 2026 in the Wikipedia article linked under it, usually the article on that landmark. No team, league, player or company is an answer, and population figures are left out because they change.
Boston is named after a market town in which English county?Answer: Lincolnshire. Source: Wikipedia: Boston
The Boston News-Letter is regarded as the first continuously published newspaper in the colony. When did it first appear?Answer: 1704. Source: Wikipedia: The Boston News-Letter
Castle Island, now home to Fort Independence, has had a fort on it since which year?Answer: 1634. Source: Wikipedia: Castle Island (Massachusetts)
In the 1630s many families used Boston Common as what?Answer: A cow pasture. Source: Wikipedia: Boston Common
In which year was Boston founded?Answer: 1630. Source: Wikipedia: Boston
Long Wharf, the historic pier on Boston Harbor, was built between 1710 and which year?Answer: 1721. Source: Wikipedia: Long Wharf (Boston)
The Old State House is the oldest public building still standing in Boston. In which year was it completed?Answer: 1713. Source: Wikipedia: Old State House (Boston)
Publick Occurrences, printed in Boston, put out its first edition in which year?Answer: 1690. Source: Wikipedia: Publick Occurrences Both Forreign and Domestick
The ships that sailed from England beginning in April 1630 are sometimes known as whose fleet?Answer: The Winthrop Fleet. Source: Wikipedia: Massachusetts Bay Colony
What is the name of the peninsula on which Boston was built?Answer: Shawmut Peninsula. Source: Wikipedia: Shawmut Peninsula
Which neighborhood is the oldest residential community in Boston?Answer: The North End. Source: Wikipedia: North End, Boston
Which phrase is used for John Winthrop's vision of the Puritan colony?Answer: A city upon a hill. Source: Wikipedia: John Winthrop
Who was the first European settler of Boston?Answer: William Blaxton. Source: Wikipedia: William Blaxton
Boston in the Revolution 12
The Bunker Hill Monument is a granite obelisk. How tall is it?Answer: 221 feet. Source: Wikipedia: Bunker Hill Monument
By which name is the Boston Massacre of March 5, 1770 known in Great Britain?Answer: The Incident on King Street. Source: Wikipedia: Boston Massacre
How long is the Freedom Trail through Boston?Answer: 2.5 miles. Source: Wikipedia: Freedom Trail
How many lanterns were lit in the steeple of Old North Church on April 18, 1775?Answer: Two. Source: Wikipedia: Old North Church
In March 1776 the Continental Army placed cannons on which heights overlooking Boston and its harbor?Answer: Dorchester Heights. Source: Wikipedia: Fortification of Dorchester Heights
In which Boston burying ground do Paul Revere, Samuel Adams and John Hancock lie?Answer: The Granary Burying Ground. Source: Wikipedia: Granary Burying Ground
Old North Church is the oldest church still standing in Boston. When was it built?Answer: 1723. Source: Wikipedia: Old North Church
On which date was the Battle of Bunker Hill fought?Answer: June 17, 1775. Source: Wikipedia: Battle of Bunker Hill
The USS Constitution, berthed in Boston, holds which standing among the world's naval vessels?Answer: The oldest still afloat. Source: Wikipedia: USS Constitution
What did some of the men at the Boston Tea Party put on as a disguise?Answer: Mohawk costumes. Source: Wikipedia: Boston Tea Party
Which Boston hall is sometimes called "the Cradle of Liberty"?Answer: Faneuil Hall. Source: Wikipedia: Faneuil Hall
Who gave the lantern signal from Old North Church?Answer: Robert Newman, the sexton of the church. Source: Wikipedia: Paul Revere's midnight ride
Boston firsts 10
The Boston Athenaeum was founded in 1807 by which club?Answer: The Anthology Club. Source: Wikipedia: Boston Athenæum
Boston Light was the first lighthouse built in what is now the United States. In which year was it first built?Answer: 1716. Source: Wikipedia: Boston Light
The Boston Post Road grew into one of the first major highways in the United States. What did it carry at first?Answer: The mail between New York and Boston. Source: Wikipedia: Boston Post Road
In which year was the Boston Public Library founded?Answer: 1848. Source: Wikipedia: Boston Public Library
In which year was the Museum of Fine Arts in Boston founded?Answer: 1870. Source: Wikipedia: Museum of Fine Arts, Boston
The Public Garden in Boston was the first of what in America?Answer: Public botanical garden. Source: Wikipedia: Boston Public Garden
Since which year have the Swan Boats carried riders in Boston?Answer: 1877. Source: Wikipedia: Swan Boats (Boston, Massachusetts)
Symphony Hall opened in 1900. What was new about the way it was designed?Answer: It was one of the first halls planned with the science of acoustics. Source: Wikipedia: Symphony Hall (Boston)
Which Boston park is the oldest city park in the United States?Answer: Boston Common. Source: Wikipedia: Boston Common
Which Boston tunnel is the oldest subway tunnel in North America?Answer: The Tremont Street subway. Source: Wikipedia: Tremont Street subway
The shape of the city 11
Before the 19th century, what was the Back Bay neighborhood?Answer: A bay. Source: Wikipedia: Back Bay, Boston
The Boston Harbor Islands are looked after as a mix of which two kinds of park?Answer: A national recreation area and a state park. Source: Wikipedia: Boston Harbor Islands National and State Park
The fire of 1872 holds which place in the history of Boston?Answer: The largest fire the city has had. Source: Wikipedia: Great Boston Fire of 1872
How tall is the Custom House Tower?Answer: 496 feet. Source: Wikipedia: Custom House Tower
The Longfellow Bridge has a nickname that comes from the shape of its towers. What is it?Answer: The Salt-and-Pepper Bridge. Source: Wikipedia: Longfellow Bridge
Near its mouth, the Charles River divides downtown Boston from which city?Answer: Cambridge. Source: Wikipedia: Charles River
What did the huge road project known as the Big Dig put underground?Answer: An elevated highway through the middle of the city. Source: Wikipedia: Big Dig
What kind of bridge is the Zakim Bridge, completed across the Charles River in 2003?Answer: A cable-stayed bridge. Source: Wikipedia: Leonard P. Zakim Bunker Hill Memorial Bridge
Which architect designed the Massachusetts State House, completed in 1798?Answer: Charles Bulfinch. Source: Wikipedia: Massachusetts State House
Which landscape architect designed the Emerald Necklace, Boston's chain of parks?Answer: Frederick Law Olmsted. Source: Wikipedia: Emerald Necklace
Which park gives its name to the Fenway-Kenmore neighborhood?Answer: The Back Bay Fens. Source: Wikipedia: Back Bay Fens
Landmarks, food and words 10
For its literary culture, Boston has been called the Athens of what?Answer: America. Source: Wikipedia: Boston
In which neighborhood is Copley Square?Answer: Back Bay. Source: Wikipedia: Copley Square
King's Chapel is housed in an 18th-century building that had which name for a time after the Revolution?Answer: The Stone Chapel. Source: Wikipedia: King's Chapel
Quincy Market is named after Josiah Quincy. Which office did he hold?Answer: Mayor of Boston. Source: Wikipedia: Quincy Market
What hangs in the House of Representatives chamber of the Massachusetts State House?Answer: A carved wooden codfish. Source: Wikipedia: Sacred Cod
What sweetens Boston baked beans?Answer: Molasses. Source: Wikipedia: Boston baked beans
When Faneuil Hall opened in 1742, what was it built to be?Answer: A marketplace and meeting hall. Source: Wikipedia: Faneuil Hall
Which architect designed Trinity Church in Boston?Answer: Henry Hobson Richardson. Source: Wikipedia: Trinity Church (Boston)
Which creature is the weathervane on top of Faneuil Hall?Answer: A grasshopper. Source: Wikipedia: Faneuil Hall
Who coined the phrase "Brahmin caste of New England", the source of the term Boston Brahmin?Answer: Oliver Wendell Holmes Sr. Source: Wikipedia: Boston Brahmin
How this list was compiled
Written for this site; nothing was copied from another list. Questions and wrong choices are our own. Each explanation restates, in our own sentences, facts from the page named and linked beside it. Each answer was checked on 2026-10-03 against that page, fetched that day: the article of the English Wikipedia (https://en.wikipedia.org, text under the CC BY-SA 4.0 license) on the place, the building or the event asked about. Every place named is a public landmark. No team, league, player or company is an answer, and no business is named. Left out on purpose: population figures and rankings, which change. Not repeated here: Boston facts that other quizzes on this site already ask, among them the Tea Party's tea and its act, Breed's Hill, who defended the soldiers of 1770, Evacuation Day, the motto of Boston Latin School, the Boston cream pie, Beantown and the marathon. Levels are our estimate: easy is fair for any table, medium suits someone who has walked the city, hard will stump most of them. Each round is stored easiest first, and each question carries the date its page was read. Licence: own work