120+ Boston Riddles with Answers
This page runs on Boston's habit of nicknaming itself: nine separate riddles describe the city and hand you Boston as the answer, from the Cradle of Liberty to the Hub of the Solar System. Around that core sit the landmarks tourists actually walk past: Fenway's Green Monster, the lanterns in the Old North Church, the golden grasshopper on Faneuil Hall. A smaller set trades history for dialect, daring you to know that a milkshake is a frappe and soda is a tonic. When this deck runs dry, the Thai riddles pick up right where these leave off.
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Three Boston riddles, answers included
- I'm a giant white bird that a person pedals across a pond in a Boston park. What am I?
- Answer: A Swan Boat
- What bronze duck family waddles forever across Boston's Public Garden?
- Answer: The Make Way for Ducklings statues
- I'm the oldest ballpark in Major League Baseball, tucked right into a Boston neighborhood. What am I?
- Answer: Fenway Park
Boston Riddles
- I'm a giant white bird that a person pedals across a pond in a Boston park. What am I?A Swan Boat
- What bronze duck family waddles forever across Boston's Public Garden?The Make Way for Ducklings statues
- I'm the oldest ballpark in Major League Baseball, tucked right into a Boston neighborhood. What am I?Fenway Park
- What 37-foot-tall wall in left field sends home run balls bouncing right back onto the grass?The Green Monster
- What giant triangle sign glows over Boston every night near Fenway Park?The Citgo sign
- What one letter is Boston's whole subway system called?The T
- I'm the oldest public park in the entire United States, sitting right in downtown Boston. What am I?Boston Common
- What Boston park sits beside the Common, famous for its swan boats?The Public Garden
- I'm a red line painted on the sidewalk for two and a half miles, leading you past almost every famous spot in old Boston. What am I?The Freedom Trail
- What Boston silversmith jumped on a horse one night in 1775 to warn everyone the British were coming?Paul Revere
- I hung two lanterns in my steeple one night to warn that the British were coming by sea. What am I?The Old North Church
- What Boston party had no cake and no balloons, and ended with hundreds of chests of tea dumped straight into the harbor?The Boston Tea Party
- I've been a marketplace and meeting hall since 1742, and a golden grasshopper sits on top of me instead of a rooster. What am I?Faneuil Hall
- What Boston market serves a dozen different lunches under one roof?Quincy Market
- What famous Boston race sends runners 26.2 miles to a finish line on Boylston Street every spring?The Boston Marathon
- I drive down the street like a bus, then splash right into the Charles River like a boat. What am I?A Boston Duck Tours boat
- What thick, creamy soup do Bostonians just call chowda?Clam chowder
- I'm a hot dog bun, but instead of a hot dog, I'm stuffed with cold lobster meat. What am I?A lobster roll
- What Boston dessert is actually a cake, filled with custard and topped with chocolate, despite its name?Boston cream pie
- What coffee chain started near Boston and fuels the entire city?Dunkin'
- I gave Boston its nickname, and I'm slow-cooked with molasses until I'm sweet and sticky. What am I?Boston baked beans
- What black and gold team skates for Boston all winter?The Boston Bruins
- Who has won more NBA championship banners than any other team?The Boston Celtics
- I'm one of the oldest, most famous universities in America, teaching students in Massachusetts since 1636. What am I?Harvard University
- What Boston-area university once had students measure an entire bridge using a classmate named Oliver Smoot as the ruler?MIT
- I'm a wooden warship so tough that cannonballs used to bounce right off my sides. Sailors call me Old Ironsides. What am I?USS Constitution
- What is the oldest lighthouse station in the United States, still flashing at the mouth of Boston Harbor?Boston Light
- What Boston accent turns park the car into pahk the cah?The Boston accent
- What sticky disaster sent a wave rolling through Boston's North End in 1919, and it definitely was not chocolate?The Great Molasses Flood
- I'm a bridge over the Charles River measured not in feet, but in one student's body length, painted on my sidewalk again and again. What am I?The Harvard Bridge
- Twin gold statues of a lion and a unicorn still perch on my balcony, symbols of a king Boston once rebelled against. What am I?The Old State House
- What Boston school, founded in 1635, is the oldest public school in the entire United States?Boston Latin School
- What hot dog is famous for being sold only at Fenway Park?A Fenway Frank
- I'm a huge group of musicians who have been playing concerts in Boston since 1881. What am I?The Boston Symphony Orchestra
- What Founding Father from Boston signed the Declaration of Independence and later had a beer named after him, though he never brewed a drop?Samuel Adams
- I share my name with a famous Boston patriot, but you'll find me in a bottle, not a history book. What am I?Sam Adams beer
- Whose signature is so big it became a synonym for signature itself?John Hancock
- I share a name with a man famous for his giant signature, but I'm made of glass and I once lost window panes in the wind. What am I?The John Hancock Tower
- What real Boston bar inspired a show where everybody knows your name?Cheers
- I started the day Boston traded away a young pitcher named Babe Ruth, and I didn't end for 86 years. What am I?The Curse of the Bambino
- What Boston museum still hangs empty frames where 13 paintings were stolen in 1990 and never recovered?The Isabella Stewart Gardner Museum
- What Boston project buried an entire elevated highway underground?The Big Dig
- I'm a rental truck that ignored the warning signs, took the wrong parkway, and got peeled open by a low stone bridge. What am I?A storrowed truck
- What do Bostonians call a traffic circle that everywhere else in America calls a roundabout?A rotary
- In parts of New England, what do you call a water fountain?A bubbler
- I'm a Boston word that means very, and I show up in front of almost every adjective around here. What word am I?Wicked
- In Boston, what do you order if you want a milkshake, since asking for a milkshake just gets you flavored milk?A frappe
- Order me regular at a Boston coffee shop and you won't get black coffee, you'll get cream and two sugars. What am I?A regular coffee
- What old-school Boston word means plain old soda pop?A tonic
- What cobblestone street on Beacon Hill is considered one of the most photographed streets in America, despite barely fitting a car?Acorn Street
- I'm a private, gated square on Beacon Hill where the front doors are famously colorful and a future secretary of state once called home. What am I?Louisburg Square
- What still light up Beacon Hill's sidewalks after dark, the old-fashioned way?The Beacon Hill gas lamps
- What Back Bay street turned its old brownstones into Boston's fanciest shops?Newbury Street
- I used to be a bargain hunter's paradise below a department store, where prices dropped automatically the longer a dress sat unsold. What am I?Filene's Basement
- What Copley Square church, finished in 1877, is considered one of the most important buildings in American architecture?Trinity Church
- What Back Bay square sits between a famous church and a famous library?Copley Square
- I was the first large free municipal library in the United States, and my courtyard makes visitors feel like they walked into Italy. What am I?The Boston Public Library
- What glass-walled Boston museum, designed by I.M. Pei, sits on the harbor honoring a president from nearby Brookline?The John F. Kennedy Presidential Library
- I'm a bridge with two tall towers shaped like a sliced obelisk, carrying traffic over the Charles River. What am I?The Zakim Bridge
- What Boston bridge is nicknamed the Salt and Pepper Bridge for the shape of its stone towers?The Longfellow Bridge
- What Boston tunnel is named after a baseball legend, not a general?The Ted Williams Tunnel
- I'm the airport where your Boston trip probably started, sitting right across the harbor from downtown. What am I?Logan International Airport
- What Boston Harbor island was literally rebuilt out of rubble from the Big Dig?Spectacle Island
- What Southie waterfront spot is actually a peninsula, not an island at all anymore?Castle Island
- I've served oysters in the same Boston building since 1826, making me the oldest continuously running restaurant in America. What am I?The Union Oyster House
- What soft, buttery dinner roll was invented at a Boston hotel and is still served at tables across America?The Parker House roll
- I'm remembered as the first person killed in the Boston Massacre, and many historians consider me the first casualty of the American Revolution. Who am I?Crispus Attucks
- What 221-foot granite obelisk in Charlestown marks a battle the British technically won, at a heavy cost?The Bunker Hill Monument
- What violent confrontation on King Street in 1770 left five colonists dead and helped ignite the American Revolution?The Boston Massacre
- I was a Boston lawyer who defended the British soldiers after the Boston Massacre, believing everyone deserved a fair trial, years before I became president. Who am I?John Adams
- What Charlestown battle did the British technically win, at a devastating cost?The Battle of Bunker Hill
- What Founding Father was born on Milk Street in Boston before running off to make his fortune in Philadelphia?Benjamin Franklin
- I burned through 65 acres of downtown Boston in a single night, destroying almost 800 buildings before firefighters finally stopped me. What am I?The Great Boston Fire of 1872
- What Boston museum holds one of the largest art collections in the entire country, spanning ancient Egypt to modern America?The Museum of Fine Arts
- Acousticians still study my concert hall as one of the best-sounding rooms ever built, thanks to math done before anyone owned a computer. What am I?Symphony Hall
- What Boston university is famous for sending students out on co-op jobs?Northeastern University
- What Boston university stretches for over a mile along Commonwealth Avenue?Boston University
- What Jesuit university just outside Boston plays its football rivalry against Notre Dame?Boston College
- I sit on a hill between Boston and Medford, and my mascot is a mildly ridiculous choice: a jumbo elephant. What am I?Tufts University
- What is the largest two-day rowing event in the world, held every fall on the Charles River?The Head of the Charles Regatta
- I freeze a Boston hockey legend mid-air, arms raised, the instant after he scored the goal that won the 1970 Stanley Cup. What am I?The Bobby Orr statue
- What Celtics legend, nicknamed the Hick from French Lick, won three NBA championships in the 1980s?Larry Bird
- I'm the last Major League Baseball player to bat over .400 in a single season, and I did it in a Red Sox uniform in 1941. Who am I?Ted Williams
- What Fenway foul pole is named after a player who barely hit any home runs there?Pesky's Pole
- What furry green mascot is named after the most famous wall in baseball?Wally the Green Monster
- I'm the arena where the Celtics and the Bruins both play, built right on top of a train station. What am I?TD Garden
- What baseball series did the Red Sox win after falling behind three games to none, the only team ever to do it?The 2004 ALCS comeback
- What Boston newspaper has been printing since 1872?The Boston Globe
- In the 1800s, I earned a nickname comparing me to an ancient Greek city, thanks to my universities, libraries, and general love of showing off how smart I was. What city am I?Boston
- What chain of connected parks winds through Boston like a green ribbon, designed by the same man who designed Central Park?The Emerald Necklace
- I designed both New York's Central Park and Boston's Emerald Necklace, and I'm considered the father of American landscape architecture. Who am I?Frederick Law Olmsted
- What Boston skyscraper's observation deck gives you a 360-degree view of the whole city?The Prudential Tower Skywalk Observatory
- My brick sidewalks host some of the priciest real estate in Boston, and a few of my old window panes have turned faintly purple with age. What neighborhood am I?Beacon Hill
- What Beacon Hill building has a dome covered in 23-karat gold leaf, gleaming over the Boston skyline?The Massachusetts State House
- I honor a young colonel and the Black soldiers of the 54th Massachusetts Regiment, standing across from the State House on Boston Common. What am I?The Robert Gould Shaw Memorial
- What small brick building in downtown Boston once housed a 19th-century publishing house that printed Hawthorne, Longfellow, and Thoreau?The Old Corner Bookstore
- I'm the oldest Black church building still standing in the United States, tucked into Beacon Hill's north slope since 1806. What am I?The African Meeting House
- What Boston neighborhood holds the largest collection of Victorian brownstones anywhere in the country?The South End
- I'm a ribbon of parks and public art running a mile and a half where an ugly elevated highway once stood, before it finally went underground. What am I?The Rose Kennedy Greenway
- What riverside park hosts free outdoor concerts every Fourth of July, right along the Charles?The Charles River Esplanade
- I'm the historic, fenced-in heart of Harvard's campus, where freshmen have been living in the same dorms since colonial times. What am I?Harvard Yard
- What member-only library, founded in 1807, has provided a peaceful reading room to Boston's book lovers for over two centuries?The Boston Athenaeum
- What city has been nicknamed the Cradle of Liberty ever since the American Revolution began within its streets?Boston
- Nineteenth-century writer Oliver Wendell Holmes called me the hub of the solar system, and locals shortened that into just one nickname. What city am I?Boston
- What major US city has streets so winding that legend blames them on colonial-era cows choosing their own paths?Boston
- I was founded in 1630 by Puritan settlers who named me after a town back in England. What city am I?Boston
- What historic Boston snowstorm dumped over two feet of snow in 1978 and shut the entire city down for a week?The Blizzard of '78
- I'm Boston's largest neighborhood by both size and population, home turf to rappers and hockey stars alike. What am I?Dorchester
- What historic Boston neighborhood was almost entirely demolished in the 1950s in the name of urban renewal, and is still mourned by former residents today?The West End
- What is one of the oldest Chinatowns on the entire East Coast?Boston's Chinatown
- I separate Boston from Cambridge, and on any sunny day you'll find rowers gliding across me. What am I?The Charles River
- What harbor once had hundreds of tea chests dumped into it, and today is clean enough to swim in?Boston Harbor
- What 34-island park hides in plain sight inside Boston Harbor?The Boston Harbor Islands
- Wait five minutes and I'll change completely, especially in spring, and locals joke about it constantly. What city's weather am I?Boston
- What city has fans who casually expect a championship parade from at least one of four major sports teams nearly every year?Boston
- I'm one of Boston's oldest neighborhoods, once my own separate town, with deep roots in the city's Black cultural history. What neighborhood am I?Roxbury
- What city's nickname comes from its old-fashioned love of a slow-cooked bean dish?Boston
- What city is both New England's biggest and the capital of Massachusetts?Boston
- What Boston neighborhood throws one of the oldest and largest Saint Patrick's Day parades in the entire country?South Boston
- I'm a floating museum with two full-scale replica ships, where visitors can toss fake tea crates into the harbor just like 1773. What am I?The Boston Tea Party Ships and Museum
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The Two Tricks Behind These Boston Riddles
Two different tricks run through this set. The first hides the city inside its own nicknames: a riddle claims I earned a nickname comparing me to an ancient Greek city or promises wait five minutes and I'll change completely, and the answer is not a landmark, it is Boston itself, so read city riddles for a slogan or a running joke before hunting for a building.
The second trick is local vocabulary, not history. Ask what Bostonians call a traffic circle and the riddles expect you to already know the answer is a rotary, not a roundabout, and the same goes for a bubbler, a tonic, or a regular coffee that arrives with cream and sugar instead of black. When a riddle sounds like plain conversation, suspect a dialect word, not a fact.
Who Reaches for a Boston Riddle
Visitors walking the Freedom Trail use this as a cheat sheet for the story behind Paul Revere's ride, the lanterns in the Old North Church, and why a golden grasshopper sits on top of Faneuil Hall instead of a rooster. Filter to Kids before a family trip and every riddle stays inside swan boats, duck statues, and the Green Monster, nothing that needs a date memorized.
Transplants and college students lean on the vocabulary riddles to stop ordering a milkshake and getting flavored milk instead of a frappe, or asking for a water fountain instead of a bubbler. Trivia hosts pull from Hard for the ringers, the Great Molasses Flood, Pesky's Pole, the Smoot measurements on the Harvard Bridge, questions built to separate the locals from the tourists.
More Boston Riddles by Type
Boston Riddles for Kids
34 kid-friendly boston riddles with simple words, safe themes, and answers that make young solvers feel clever.
Example Boston Riddles for Kids
- I'm a giant white bird that a person pedals across a pond in a Boston park. What am I? A Swan Boat
- What bronze duck family waddles forever across Boston's Public Garden? The Make Way for Ducklings statues
- I'm the oldest ballpark in Major League Baseball, tucked right into a Boston neighborhood. What am I? Fenway Park
- What 37-foot-tall wall in left field sends home run balls bouncing right back onto the grass? The Green Monster
Hard Boston Riddles
For solvers who like a fight: 37 hard boston riddles that resist the first guess, and often the second.
Example Hard Boston Riddles
- What sticky disaster sent a wave rolling through Boston's North End in 1919, and it definitely was not chocolate? The Great Molasses Flood
- I'm a bridge over the Charles River measured not in feet, but in one student's body length, painted on my sidewalk again and again. What am I? The Harvard Bridge
- Twin gold statues of a lion and a unicorn still perch on my balcony, symbols of a king Boston once rebelled against. What am I? The Old State House
- What Boston school, founded in 1635, is the oldest public school in the entire United States? Boston Latin School
Boston Riddles for Adults
34 boston riddles with grown-up wit: subtler wordplay and references, zero crudeness, all challenge.
Example Boston Riddles for Adults
- What violent confrontation on King Street in 1770 left five colonists dead and helped ignite the American Revolution? The Boston Massacre
- I was a Boston lawyer who defended the British soldiers after the Boston Massacre, believing everyone deserved a fair trial, years before I became president. Who am I? John Adams
- What Charlestown battle did the British technically win, at a devastating cost? The Battle of Bunker Hill
- What Founding Father was born on Milk Street in Boston before running off to make his fortune in Philadelphia? Benjamin Franklin
Funny Boston Riddles
The punchline crowd: 42 boston riddles built for a laugh, with puns, twists and groan-worthy wordplay included.
Example Funny Boston Riddles
- What giant triangle sign glows over Boston every night near Fenway Park? The Citgo sign
- What one letter is Boston's whole subway system called? The T
- I'm the oldest public park in the entire United States, sitting right in downtown Boston. What am I? Boston Common
- What Boston park sits beside the Common, famous for its swan boats? The Public Garden
Easy Boston Riddles
Warm up with 41 easy boston riddles for quick wins to build momentum before the tricky ones.
Example Easy Boston Riddles
- I'm a red line painted on the sidewalk for two and a half miles, leading you past almost every famous spot in old Boston. What am I? The Freedom Trail
- What Boston party had no cake and no balloons, and ended with hundreds of chests of tea dumped straight into the harbor? The Boston Tea Party
- What Boston market serves a dozen different lunches under one roof? Quincy Market
- What famous Boston race sends runners 26.2 miles to a finish line on Boylston Street every spring? The Boston Marathon
Tricky Boston Riddles
34 tricky boston riddles that bait the obvious answer, so read slowly, the trap is in the wording.
Example Tricky Boston Riddles
- What Founding Father from Boston signed the Declaration of Independence and later had a beer named after him, though he never brewed a drop? Samuel Adams
- I share my name with a famous Boston patriot, but you'll find me in a bottle, not a history book. What am I? Sam Adams beer
- Whose signature is so big it became a synonym for signature itself? John Hancock
- I share a name with a man famous for his giant signature, but I'm made of glass and I once lost window panes in the wind. What am I? The John Hancock Tower
What Am I Boston Riddles
The classic guessing game: 48 what-am-I boston riddles that describe themselves clue by clue. Read, commit to a guess, then reveal.
Example What Am I Boston Riddles
- I hung two lanterns in my steeple one night to warn that the British were coming by sea. What am I? The Old North Church
- I've been a marketplace and meeting hall since 1742, and a golden grasshopper sits on top of me instead of a rooster. What am I? Faneuil Hall
- I drive down the street like a bus, then splash right into the Charles River like a boat. What am I? A Boston Duck Tours boat
- I'm a hot dog bun, but instead of a hot dog, I'm stuffed with cold lobster meat. What am I? A lobster roll
Clever Boston Riddles
44 boston riddles built on a genuinely neat idea rather than a trap: fair on the first read, satisfying on the reveal.
Example Clever Boston Riddles
- What Boston silversmith jumped on a horse one night in 1775 to warn everyone the British were coming? Paul Revere
- I gave Boston its nickname, and I'm slow-cooked with molasses until I'm sweet and sticky. What am I? Boston baked beans
- What Boston-area university once had students measure an entire bridge using a classmate named Oliver Smoot as the ruler? MIT
- I'm a wooden warship so tough that cannonballs used to bounce right off my sides. Sailors call me Old Ironsides. What am I? USS Constitution
Long Boston Riddles
85 boston riddles with a full setup and room for real misdirection, the ones worth reading out loud.
Example Long Boston Riddles
- What Boston dessert is actually a cake, filled with custard and topped with chocolate, despite its name? Boston cream pie
- I'm one of the oldest, most famous universities in America, teaching students in Massachusetts since 1636. What am I? Harvard University
- What is the oldest lighthouse station in the United States, still flashing at the mouth of Boston Harbor? Boston Light
- I'm a huge group of musicians who have been playing concerts in Boston since 1881. What am I? The Boston Symphony Orchestra
Boston Riddles to Ask Your Friends
34 boston riddles built to stump someone: text one without the answer, watch them squirm, then enjoy the reveal.
Example Boston Riddles to Ask Your Friends
- What real Boston bar inspired a show where everybody knows your name? Cheers
- I started the day Boston traded away a young pitcher named Babe Ruth, and I didn't end for 86 years. What am I? The Curse of the Bambino
- What Boston museum still hangs empty frames where 13 paintings were stolen in 1990 and never recovered? The Isabella Stewart Gardner Museum
- What Boston project buried an entire elevated highway underground? The Big Dig
Short Boston Riddles
In a hurry? 35 bite-size boston riddles that get to the point in one line, perfect to text a friend.
Example Short Boston Riddles
- What thick, creamy soup do Bostonians just call chowda? Clam chowder
- What coffee chain started near Boston and fuels the entire city? Dunkin'
- What black and gold team skates for Boston all winter? The Boston Bruins
- Who has won more NBA championship banners than any other team? The Boston Celtics
All 120 Boston Riddles with Answers
1. I'm a giant white bird that a person pedals across a pond in a Boston park. What am I?
Answer: A Swan Boat
2. What bronze duck family waddles forever across Boston's Public Garden?
Answer: The Make Way for Ducklings statues
3. I'm the oldest ballpark in Major League Baseball, tucked right into a Boston neighborhood. What am I?
Answer: Fenway Park
4. What 37-foot-tall wall in left field sends home run balls bouncing right back onto the grass?
Answer: The Green Monster
5. What giant triangle sign glows over Boston every night near Fenway Park?
Answer: The Citgo sign
6. What one letter is Boston's whole subway system called?
Answer: The T
7. I'm the oldest public park in the entire United States, sitting right in downtown Boston. What am I?
Answer: Boston Common
8. What Boston park sits beside the Common, famous for its swan boats?
Answer: The Public Garden
9. I'm a red line painted on the sidewalk for two and a half miles, leading you past almost every famous spot in old Boston. What am I?
Answer: The Freedom Trail
10. What Boston silversmith jumped on a horse one night in 1775 to warn everyone the British were coming?
Answer: Paul Revere
11. I hung two lanterns in my steeple one night to warn that the British were coming by sea. What am I?
Answer: The Old North Church
12. What Boston party had no cake and no balloons, and ended with hundreds of chests of tea dumped straight into the harbor?
Answer: The Boston Tea Party
13. I've been a marketplace and meeting hall since 1742, and a golden grasshopper sits on top of me instead of a rooster. What am I?
Answer: Faneuil Hall
14. What Boston market serves a dozen different lunches under one roof?
Answer: Quincy Market
15. What famous Boston race sends runners 26.2 miles to a finish line on Boylston Street every spring?
Answer: The Boston Marathon
16. I drive down the street like a bus, then splash right into the Charles River like a boat. What am I?
Answer: A Boston Duck Tours boat
17. What thick, creamy soup do Bostonians just call chowda?
Answer: Clam chowder
18. I'm a hot dog bun, but instead of a hot dog, I'm stuffed with cold lobster meat. What am I?
Answer: A lobster roll
19. What Boston dessert is actually a cake, filled with custard and topped with chocolate, despite its name?
Answer: Boston cream pie
20. What coffee chain started near Boston and fuels the entire city?
Answer: Dunkin'
21. I gave Boston its nickname, and I'm slow-cooked with molasses until I'm sweet and sticky. What am I?
Answer: Boston baked beans
22. What black and gold team skates for Boston all winter?
Answer: The Boston Bruins
23. Who has won more NBA championship banners than any other team?
Answer: The Boston Celtics
24. I'm one of the oldest, most famous universities in America, teaching students in Massachusetts since 1636. What am I?
Answer: Harvard University
25. What Boston-area university once had students measure an entire bridge using a classmate named Oliver Smoot as the ruler?
Answer: MIT
26. I'm a wooden warship so tough that cannonballs used to bounce right off my sides. Sailors call me Old Ironsides. What am I?
Answer: USS Constitution
27. What is the oldest lighthouse station in the United States, still flashing at the mouth of Boston Harbor?
Answer: Boston Light
28. What Boston accent turns park the car into pahk the cah?
Answer: The Boston accent
29. What sticky disaster sent a wave rolling through Boston's North End in 1919, and it definitely was not chocolate?
Answer: The Great Molasses Flood
30. I'm a bridge over the Charles River measured not in feet, but in one student's body length, painted on my sidewalk again and again. What am I?
Answer: The Harvard Bridge
31. Twin gold statues of a lion and a unicorn still perch on my balcony, symbols of a king Boston once rebelled against. What am I?
Answer: The Old State House
32. What Boston school, founded in 1635, is the oldest public school in the entire United States?
Answer: Boston Latin School
33. What hot dog is famous for being sold only at Fenway Park?
Answer: A Fenway Frank
34. I'm a huge group of musicians who have been playing concerts in Boston since 1881. What am I?
Answer: The Boston Symphony Orchestra
35. What Founding Father from Boston signed the Declaration of Independence and later had a beer named after him, though he never brewed a drop?
Answer: Samuel Adams
36. I share my name with a famous Boston patriot, but you'll find me in a bottle, not a history book. What am I?
Answer: Sam Adams beer
37. Whose signature is so big it became a synonym for signature itself?
Answer: John Hancock
38. I share a name with a man famous for his giant signature, but I'm made of glass and I once lost window panes in the wind. What am I?
Answer: The John Hancock Tower
39. What real Boston bar inspired a show where everybody knows your name?
Answer: Cheers
40. I started the day Boston traded away a young pitcher named Babe Ruth, and I didn't end for 86 years. What am I?
Answer: The Curse of the Bambino
41. What Boston museum still hangs empty frames where 13 paintings were stolen in 1990 and never recovered?
Answer: The Isabella Stewart Gardner Museum
42. What Boston project buried an entire elevated highway underground?
Answer: The Big Dig
43. I'm a rental truck that ignored the warning signs, took the wrong parkway, and got peeled open by a low stone bridge. What am I?
Answer: A storrowed truck
44. What do Bostonians call a traffic circle that everywhere else in America calls a roundabout?
Answer: A rotary
45. In parts of New England, what do you call a water fountain?
Answer: A bubbler
46. I'm a Boston word that means very, and I show up in front of almost every adjective around here. What word am I?
Answer: Wicked
47. In Boston, what do you order if you want a milkshake, since asking for a milkshake just gets you flavored milk?
Answer: A frappe
48. Order me regular at a Boston coffee shop and you won't get black coffee, you'll get cream and two sugars. What am I?
Answer: A regular coffee
49. What old-school Boston word means plain old soda pop?
Answer: A tonic
50. What cobblestone street on Beacon Hill is considered one of the most photographed streets in America, despite barely fitting a car?
Answer: Acorn Street
51. I'm a private, gated square on Beacon Hill where the front doors are famously colorful and a future secretary of state once called home. What am I?
Answer: Louisburg Square
52. What still light up Beacon Hill's sidewalks after dark, the old-fashioned way?
Answer: The Beacon Hill gas lamps
53. What Back Bay street turned its old brownstones into Boston's fanciest shops?
Answer: Newbury Street
54. I used to be a bargain hunter's paradise below a department store, where prices dropped automatically the longer a dress sat unsold. What am I?
Answer: Filene's Basement
55. What Copley Square church, finished in 1877, is considered one of the most important buildings in American architecture?
Answer: Trinity Church
56. What Back Bay square sits between a famous church and a famous library?
Answer: Copley Square
57. I was the first large free municipal library in the United States, and my courtyard makes visitors feel like they walked into Italy. What am I?
Answer: The Boston Public Library
58. What glass-walled Boston museum, designed by I.M. Pei, sits on the harbor honoring a president from nearby Brookline?
Answer: The John F. Kennedy Presidential Library
59. I'm a bridge with two tall towers shaped like a sliced obelisk, carrying traffic over the Charles River. What am I?
Answer: The Zakim Bridge
60. What Boston bridge is nicknamed the Salt and Pepper Bridge for the shape of its stone towers?
Answer: The Longfellow Bridge
61. What Boston tunnel is named after a baseball legend, not a general?
Answer: The Ted Williams Tunnel
62. I'm the airport where your Boston trip probably started, sitting right across the harbor from downtown. What am I?
Answer: Logan International Airport
63. What Boston Harbor island was literally rebuilt out of rubble from the Big Dig?
Answer: Spectacle Island
64. What Southie waterfront spot is actually a peninsula, not an island at all anymore?
Answer: Castle Island
65. I've served oysters in the same Boston building since 1826, making me the oldest continuously running restaurant in America. What am I?
Answer: The Union Oyster House
66. What soft, buttery dinner roll was invented at a Boston hotel and is still served at tables across America?
Answer: The Parker House roll
67. I'm remembered as the first person killed in the Boston Massacre, and many historians consider me the first casualty of the American Revolution. Who am I?
Answer: Crispus Attucks
68. What 221-foot granite obelisk in Charlestown marks a battle the British technically won, at a heavy cost?
Answer: The Bunker Hill Monument
69. What violent confrontation on King Street in 1770 left five colonists dead and helped ignite the American Revolution?
Answer: The Boston Massacre
70. I was a Boston lawyer who defended the British soldiers after the Boston Massacre, believing everyone deserved a fair trial, years before I became president. Who am I?
Answer: John Adams
71. What Charlestown battle did the British technically win, at a devastating cost?
Answer: The Battle of Bunker Hill
72. What Founding Father was born on Milk Street in Boston before running off to make his fortune in Philadelphia?
Answer: Benjamin Franklin
73. I burned through 65 acres of downtown Boston in a single night, destroying almost 800 buildings before firefighters finally stopped me. What am I?
Answer: The Great Boston Fire of 1872
74. What Boston museum holds one of the largest art collections in the entire country, spanning ancient Egypt to modern America?
Answer: The Museum of Fine Arts
75. Acousticians still study my concert hall as one of the best-sounding rooms ever built, thanks to math done before anyone owned a computer. What am I?
Answer: Symphony Hall
76. What Boston university is famous for sending students out on co-op jobs?
Answer: Northeastern University
77. What Boston university stretches for over a mile along Commonwealth Avenue?
Answer: Boston University
78. What Jesuit university just outside Boston plays its football rivalry against Notre Dame?
Answer: Boston College
79. I sit on a hill between Boston and Medford, and my mascot is a mildly ridiculous choice: a jumbo elephant. What am I?
Answer: Tufts University
80. What is the largest two-day rowing event in the world, held every fall on the Charles River?
Answer: The Head of the Charles Regatta
81. I freeze a Boston hockey legend mid-air, arms raised, the instant after he scored the goal that won the 1970 Stanley Cup. What am I?
Answer: The Bobby Orr statue
82. What Celtics legend, nicknamed the Hick from French Lick, won three NBA championships in the 1980s?
Answer: Larry Bird
83. I'm the last Major League Baseball player to bat over .400 in a single season, and I did it in a Red Sox uniform in 1941. Who am I?
Answer: Ted Williams
84. What Fenway foul pole is named after a player who barely hit any home runs there?
Answer: Pesky's Pole
85. What furry green mascot is named after the most famous wall in baseball?
Answer: Wally the Green Monster
86. I'm the arena where the Celtics and the Bruins both play, built right on top of a train station. What am I?
Answer: TD Garden
87. What baseball series did the Red Sox win after falling behind three games to none, the only team ever to do it?
Answer: The 2004 ALCS comeback
88. What Boston newspaper has been printing since 1872?
Answer: The Boston Globe
89. In the 1800s, I earned a nickname comparing me to an ancient Greek city, thanks to my universities, libraries, and general love of showing off how smart I was. What city am I?
Answer: Boston
90. What chain of connected parks winds through Boston like a green ribbon, designed by the same man who designed Central Park?
Answer: The Emerald Necklace
91. I designed both New York's Central Park and Boston's Emerald Necklace, and I'm considered the father of American landscape architecture. Who am I?
Answer: Frederick Law Olmsted
92. What Boston skyscraper's observation deck gives you a 360-degree view of the whole city?
Answer: The Prudential Tower Skywalk Observatory
93. My brick sidewalks host some of the priciest real estate in Boston, and a few of my old window panes have turned faintly purple with age. What neighborhood am I?
Answer: Beacon Hill
94. What Beacon Hill building has a dome covered in 23-karat gold leaf, gleaming over the Boston skyline?
Answer: The Massachusetts State House
95. I honor a young colonel and the Black soldiers of the 54th Massachusetts Regiment, standing across from the State House on Boston Common. What am I?
Answer: The Robert Gould Shaw Memorial
96. What small brick building in downtown Boston once housed a 19th-century publishing house that printed Hawthorne, Longfellow, and Thoreau?
Answer: The Old Corner Bookstore
97. I'm the oldest Black church building still standing in the United States, tucked into Beacon Hill's north slope since 1806. What am I?
Answer: The African Meeting House
98. What Boston neighborhood holds the largest collection of Victorian brownstones anywhere in the country?
Answer: The South End
99. I'm a ribbon of parks and public art running a mile and a half where an ugly elevated highway once stood, before it finally went underground. What am I?
Answer: The Rose Kennedy Greenway
100. What riverside park hosts free outdoor concerts every Fourth of July, right along the Charles?
Answer: The Charles River Esplanade
101. I'm the historic, fenced-in heart of Harvard's campus, where freshmen have been living in the same dorms since colonial times. What am I?
Answer: Harvard Yard
102. What member-only library, founded in 1807, has provided a peaceful reading room to Boston's book lovers for over two centuries?
Answer: The Boston Athenaeum
103. What city has been nicknamed the Cradle of Liberty ever since the American Revolution began within its streets?
Answer: Boston
104. Nineteenth-century writer Oliver Wendell Holmes called me the hub of the solar system, and locals shortened that into just one nickname. What city am I?
Answer: Boston
105. What major US city has streets so winding that legend blames them on colonial-era cows choosing their own paths?
Answer: Boston
106. I was founded in 1630 by Puritan settlers who named me after a town back in England. What city am I?
Answer: Boston
107. What historic Boston snowstorm dumped over two feet of snow in 1978 and shut the entire city down for a week?
Answer: The Blizzard of '78
108. I'm Boston's largest neighborhood by both size and population, home turf to rappers and hockey stars alike. What am I?
Answer: Dorchester
109. What historic Boston neighborhood was almost entirely demolished in the 1950s in the name of urban renewal, and is still mourned by former residents today?
Answer: The West End
110. What is one of the oldest Chinatowns on the entire East Coast?
Answer: Boston's Chinatown
111. I separate Boston from Cambridge, and on any sunny day you'll find rowers gliding across me. What am I?
Answer: The Charles River
112. What harbor once had hundreds of tea chests dumped into it, and today is clean enough to swim in?
Answer: Boston Harbor
113. What 34-island park hides in plain sight inside Boston Harbor?
Answer: The Boston Harbor Islands
114. Wait five minutes and I'll change completely, especially in spring, and locals joke about it constantly. What city's weather am I?
Answer: Boston
115. What city has fans who casually expect a championship parade from at least one of four major sports teams nearly every year?
Answer: Boston
116. I'm one of Boston's oldest neighborhoods, once my own separate town, with deep roots in the city's Black cultural history. What neighborhood am I?
Answer: Roxbury
117. What city's nickname comes from its old-fashioned love of a slow-cooked bean dish?
Answer: Boston
118. What city is both New England's biggest and the capital of Massachusetts?
Answer: Boston
119. What Boston neighborhood throws one of the oldest and largest Saint Patrick's Day parades in the entire country?
Answer: South Boston
120. I'm a floating museum with two full-scale replica ships, where visitors can toss fake tea crates into the harbor just like 1773. What am I?
Answer: The Boston Tea Party Ships and Museum
That's all 120, solved, peeked, or saved for later. The generator up top can re-deal them in any order, or filter down to exactly the kind you want.
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