245 Boston Trivia Questions (Ranked From Easiest to Hardest)

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245 Boston Trivia Questions Ranked From Easiest to Hardest (Updated For 2024)

1. One of Boston's best-known skyscrapers, "The Pru's" nickname is short for the name of what insurance company?
   
   Answer: Prudential
   
   
2. The "Boston" breed of what dog type is sometimes adorably known as the "American gentleman?" These dogs are also the mascot of Boston University.
   
   Answer: Terrier
   
   
3. Glitzy shops like Bulgari, Diane von Furstenberg, and Longchamp line what posh shopping street in Boston's Back Bay neighborhood?
   
   Answer: Newbury Street
   
   
4. Frederick Law Olmsted designed a chain of green spaces across the Boston peninsula, that are called a "necklace" of what apt type of jewel?
   
   Answer: Emerald
   
   
5. A large brown bear named Blades is the mascot of what Boston professional sports team?
   
   Answer: Boston Bruins
   
   
6. An undercover cop and a mole in the police each try to figure out who the other is while infiltrating an Irish gang in South Boston, in what 2006 Martin Scorsese film?
   
   Answer: The Departed
   
   
7. A landmark on N Square in Boston is the colonial home of what Revolutionary American hero? He is known to have said “One if by land, two if by sea.”
   
   Answer: Paul Revere House
   
   
8. What beer, the flagship brand of the Boston Beer Company, was named after a US founding father who led pro-American and anti-British propaganda efforts and was the cousin of future president John?
   
   Answer: Samuel Adams
   
   
9. The superstition that the Red Sox's 86-year championship drought from 1918 to 2004 was caused by the departure of Babe Ruth from the team was known as "The Curse of the" WHAT?
   
   Answer: Bambino
   
   
10. Basketball Hall of Famer Larry "Legend" Bird played his entire NBA career with what Eastern Conference team?
    
    Answer: Boston Celtics
    
    
11. Inspired by a long-distance event in the 1896 Summer Olympics, what famous American race takes place annually in Massachusetts in April on Patriot's Day?
    
    Answer: Boston Marathon
    
    
12. "Boston Rob" Mariano became famous in 2002 when he competed in the Marquesas Islands on season 4 of what CBS reality series?
    
    Answer: Survivor
    
    
13. What Boston college, known for its study of jazz and other contemporary American music, has produced more Grammy-winners than any other school?
    
    Answer: Berklee College of Music
    
    
14. While building magnetrons at MIT in the 1940s, Percy Spencer noticed a melting chocolate bar in his pocket. Deeper investigation and exploration led to the invention of what household device? Spencer received no royalties for this invention, first marketed as the Radarange.
    
    Answer: Microwave
    
    
15. "Best of Enemies" is an ESPN "30 for 30" documentary on the 1980s rivalry between the Boston Celtics and what other NBA team?
    
    Answer: Los Angeles Lakers
    
    
16. Inspired by the 1896 Summer Olympics, what Boston tradition began in 1897? It wasn't held in 2020 (and was held later than usual in 2021) due to the COVID pandemic.
    
    Answer: Boston Marathon
    
    
17. Which public park in the city is, in fact, the oldest in the United States since it was established in 1634?
    
    Answer: Boston Common
    
    
18. In 1917, a Canadian company named Salada opened a U.S. headquarters in Boston's Back Bay, commissioning from Henry Wilson a set of ornate doors that detail the production of what beverage_strongly associated with the city in a different, earlier context?
    
    Answer: Tea
    
    
19. Boston native Uzo Aduba is known for playing inmate Suzanne "Crazy Eyes" Warren on what "colorful" Netflix series?
    
    Answer: Orange Is the New Black
    
    
20. What heavy frigate, also nicknamed Old Ironsides, was built in 1794 by the U.S. Navy, and now is on display in Boston suburb Charlestown, MA? Its name is the same venerated document that outlines the federal rules of the United States.
    
    Answer: USS Constitution
    
    
21. In 1964, the Boston Globe announced an annual tournament in what type of bowling, unique to New England, and which uses a small handheld ball and narrow pins?
    
    Answer: Candlepin Bowling
    
    
22. Ruggles, Stony Brook, Assembly, and Chinatown are all stops on which of Boston's MBTA train routes?
    
    Answer: Orange Line
    
    
23. Coffee became more popular in America in the 1770s. At the time, many people had stopped drinking tea as a patriotic act. What was the name of the famous protest that inspired them to boycott the beverage?
    
    Answer: The Boston Tea Party
    
    
24. If you want to catch a Bruins or Celtics game, you know that they play at which arena above North Station?
    
    Answer: TD Garden
    
    
25. What Boston sports star gives his name to an underwater automobile traffic tunnel that is, at 90 feet below ground, the deepest of its kind in America?
    
    Answer: Ted Williams
    
    
26. What American fast casual restaurant, formerly known as Boston Chicken, was founded in Newton, MA in 1984? While the company headquarters have since moved to Colorado, the chain sticks to its proud Boston namesake roots.
    
    Answer: Boston Market
    
    
27. Known in the U.S. as the Intolerable Acts and in the UK as the Coercive Acts, this series of restrictive laws was passed in response to what iconic, rebellious American event that occurred on December 16, 1773?
    
    Answer: Boston Tea Party
    
    
28. What is the name of Boston's mass transit pass, which comes from a 1949 mayoral candidate's campaign song about a traveler who couldn't pay the exit fare to get out of the T?
    
    Answer: CharlieCard
    
    
29. Musicians Joe Perry and Steven Tyler moved to Boston in 1969, starting a group called Jam Band, which would eventually become what legendary rock and roll band?
    
    Answer: Aerosmith
    
    
30. Zoo New England operates a zoo based out of what Boston park that shares its “F” name with the surname of a Founding Father who invented bifocals?
    
    Answer: Franklin Park Zoo
    
    
31. Also the name of an NFL team located about 300 miles from Boston, what is the name of the sports teams of Boston College?
    
    Answer: Eagles
    
    
32. Boston is located in Suffolk County. Name ANY of the counties that Suffolk County borders.
    
    Answer: Essex County (north) Norfolk County (south) Middlesex County (west)
    
    
33. Medical facilities including Beth Israel Deaconess Medical Center, Brigham and Women's Hospital, Boston Children's Hospital, Dana–Farber Cancer Institute, and Harvard Medical School are all located in what "L" Medical and Academic Area in Boston?
    
    Answer: Longwood
    
    
34. Which Boston University has the nickname "Huskies," competes in the Colonial Athletic Association, and is located in the Fenway, Roxbury, South End, and Back Bay neighborhoods adjacent to Huntington Avenue near the Museum of Fine Arts and Symphony Hall?
    
    Answer: Northeastern University
    
    
35. "Boston Rob" Mariano and his wife, Amber Brkich, famously met as contestants on "Survivor" and went on to compete as a team on two seasons of what around-the-world reality show?
    
    Answer: The Amazing Race
    
    
36. Boston Globe editor Ben Bradlee, Jr. headed up what infamous investigative reporting unit of The Boston Globe, later memorialized in an award-winning film?
    
    Answer: Spotlight
    
    
37. Which American insurer founded in 1912 is headquartered in Boston but has an NYC landmark in its logo? (Hint: You might recall the company’s mascot—an emu—from the TV commercials)
    
    Answer: Liberty Mutual
    
    
38. From his laboratory in Boston, Alexander Graham Bell made the world's first phone call in 1876, telling his assistant to "...come here." What was the name of the assistant he beckoned, who coincidentally shared the last name of a fictional detective's sidekick?
    
    Answer: Watson
    
    
39. Edward Lawrence Logan, the namesake of Boston's international airport, first enlisted in the military during the Spanish-American War and later rose to the rank of major general following his efforts in what global conflict?
    
    Answer: The First World War
    
    
40. 2022 Boston Marathon winners Evans Chebet and Peres Jepchirchir are both from what African nation famed for its many successful distance runners?
    
    Answer: Kenya
    
    
41. The King's Chapel Burying Ground in Boston contains the graves of Massachusetts' first governor as well as of Mary Chilton, the first woman to step off what famous Pilgrim ship?
    
    Answer: Mayflower
    
    
42. The largest art heist in the city of Boston's history occurred at which of the city's museums in 1990?
    
    Answer: Isabella Stewart Gardner Museum
    
    
43. What megaproject, known for its delays and cost overruns, rerouted I-93 into a tunnel through the heart of downtown Boston?
    
    Answer: Central Artery/Tunnel Project
    
    
44. Following his 12-season NHL career spanning from 1966-1979, the Boston Bruins retired what Canadian defensemen’s number 4 in 1979 – the same year he was inducted into the Hockey Hall of Fame?
    
    Answer: Bobby Orr
    
    
45. In 2003, Nike purchased a footwear company that was founded almost 100 years prior in Massachusetts. This acquired company dominated the "court shoe" market for decades and pivoted to military boot manufacturing during WWII. What is this brand, which owns the Jack Purcell and Star Chevron trademarks?
    
    Answer: Converse
    
    
46. In 1678, Boston hired Thomas Atkins to be the first chief of a newly founded paid (non-volunteer) department. This group's primary purpose was to fight what type of object?
    
    Answer: Fires
    
    
47. What "Parks and Recreation" star was born in Newton, went to Boston College, and is a Red Sox fan, but called the Boston accent "disgusting" in a 2014 BuzzFeed interview?
    
    Answer: Amy Poehler
    
    
48. Ask those "saints" from that gun-happy Boston movie or Little Big Town: Tagalog for "mountain" somehow gave us what word for a place out in the middle of nowhere?
    
    Answer: Boondock
    
    
49. What Boston-based battle of the American Revolutionary War is somewhat inaccurately named, since most of the fighting took place on Breed's Hill?
    
    Answer: Battle of Bunker Hill
    
    
50. Sam Malone and Diane Chambers are two of the main characters in what American sitcom television series that earned a top-ten rating during eight of its 11 seasons?
    
    Answer: Cheers
    
    
51. In 1963, he accepted a challenge from the CEO of The Boston Company to create a consulting arm for the bank. The consulting arm initially operated as a subsidiary of the Boston Safe Deposit and Trust Company. Billings for the first month were only US$500. Who?
    
    Answer: Bruce Henderson
    
    
52. Famously portrayed by Meryl Streep on film, what "French Chef" made her home in Cambridge for four decades, from 1961 to 2001?
    
    Answer: Julia Child
    
    
53. The Long Island hospital in Boston Harbor inspired Dennis Lehane to write what 2003 horror novel, which was adapted into a 2010 film starring Leonardo DiCaprio?
    
    Answer: Shutter Island
    
    
54. In which Boston neighborhood will you come across the Ella J. Baker House, the Franklin Park Zoo, and the John F. Kennedy Presidential Library and Museum?
    
    Answer: Dorchester
    
    
55. Which NFL team, established in Boston in 1932, moved to its current location in 1937 and chose its current team name in 2022?
    
    Answer: Washington Commanders
    
    
56. Fort Independence is a granite military structure and one of the oldest continuously fortified sites in the United States, operating since 1634. The Fort now lies within a preserved state park on what misnomer-ed "Island?"
    
    Answer: Castle Island
    
    
57. A small plaza at Boylston St. and Charles St. near Boston Common was renamed in 2009 for what author, near the house where he was born in 1809?
    
    Answer: Edgar Allan Poe
    
    
58. What regatta, the largest two-day rowing event in the world, is held annually on the river that separates Boston from Cambridge?
    
    Answer: Head of the Charles
    
    
59. Based out of Boston, what multinational financial institution offers managed stock accounts for its clients? Its logo is a light shining on top of a pyramid, and its name is a word meaning faithfulness.
    
    Answer: Fidelity investments
    
    
60. Appropriately given the STEM focus of the school, the sports teams of the Massachusetts Institute of Technology are known by what professional-sounding name?
    
    Answer: Engineers
    
    
61. The first structure of what type was built on Boston Harbor's Little Brewster Island in 1716? The one standing there today dates back to 1783, and is the second oldest structure of its type in the U.S.
    
    Answer: Lighthouse
    
    
62. What is the name for Amtrak's high-speed service connecting Boston and Washington DC with major stops in New York City, Philadelphia, and Baltimore?
    
    Answer: Acela
    
    
63. A large, double-sided sign featuring the logo of an oil company overlooks Kenmore Square in Boston. The sign was first installed in 1940 and most recently had its logo updated in 1965. What brand is represented on this sign?
    
    Answer: Citgo
    
    
64. The Boston Marathon begins in Hopkinton, Massachusetts and ends in Copley Square at what landmark Boston building, designed by architect Charles McKim?
    
    Answer: Boston Central Library
    
    
65. The Central Artery/Tunnel Project, a Boston-area project that rerouted I-93 and was plagued by delays and cost overruns, was better known by what rhyming nickname?
    
    Answer: The Big Dig
    
    
66. A single red seat at Boston's Fenway Park marks the spot where what Red Sox star hit a 500-ft. homer in 1946, still the longest in stadium history?
    
    Answer: Ted Williams
    
    
67. Which Neil Diamond song is played in the middle of the eighth inning at every Boston Red Sox home game, since 2002?
    
    Answer: Sweet Caroline
    
    
68. With a name that refers to the club's famous wall in left field, Wally the Green Monster is the mascot of what Major League Baseball team?
    
    Answer: Boston Red Sox
    
    
69. Fort Independence is a pre-Revolutionary War facility located on what medieval-sounding island in Boston harbor?
    
    Answer: Castle Island
    
    
70. What famed Massachusetts act traditionally performs on the Esplanade every Fourth of July?
    
    Answer: Boston Pops
    
    
71. What “E” online newspaper, founded in 2021 by Boston Globe staff members, is named after an anti-slavery newspaper that was founded in 1833, and pledges itself to discuss modern racial inequality? Its name literally means a person or entity that frees slaves.
    
    Answer: The Emancipator
    
    
72. What "amphibious" water feature is the home of Boston Common's winter skating activities?
    
    Answer: Frog Pond
    
    
73. What Boston Celtics legend, who played for the team from 1979 to 1992, had a nickname that reflected his Indiana origins — "The Hick from French Lick?"
    
    Answer: Larry Bird
    
    
74. Developed at MIT and at Boston Dynamics, Spot is a contact-free robot who helps with basic patient care and is mounted on a body with what guessable number of legs?
    
    Answer: Four
    
    
75. The oldest subway tunnel in North America is the Tremont Street subway in what American city?
    
    Answer: Boston
    
    
76. Steinert Hall is a hidden concert hall built four floors below its eponymous store on Boylston Street in Boston which vends what musical instrument?
    
    Answer: Piano
77. An annual ice hockey tournament between four Boston-area colleges, held in February at TD Garden, is colloquially known by what culinary name?
    
    Answer: Beanpot
    
    
78. The Arthur Fiedler Footbridge provides access to the Charles River bandshell, and passes above what thoroughfare? Multiple times, traffic on the thoroughfare has been disrupted due to a U-Haul getting stuck under an overpass.
    
    Answer: Storrow Drive
    
    
79. Although kissing runners was not allowed in 2021, the "scream tunnel" is an iconic portion of the Boston Marathon in which runners pass through the campus of what all-women's school?
    
    Answer: Wellesley College
    
    
80. The International Sand Sculpting Competition is hosted at America's first public beach, which happens to be located in the Boston Area. What is the name of this beach?
    
    Answer: Revere Beach
    
    
81. Led by Keith Lockhart since 1995, what Beantown institution of light classical music has also had such illustrious music directors as John Williams and Arthur Fiedler?
    
    Answer: Boston Pops
    
    
82. Boston-area restaurant chain Kelly's claims to be the birthplace of what particular sandwich, which at Kelly's includes mayonnaise, American cheese, barbecue sauce, and the namesake meat?
    
    Answer: Roast Beef Sandwich
    
    
83. In 1954, surgeons in Boston performed the first successful human organ transplant when they took what organ from one twin and gave it to the other?
    
    Answer: Kidney
    
    
84. Harpoon in Boston, Sand Creek in Wisconsin, and O'Fallon in Missouri all have a chocolate-flavored product which is what type of beer?
    
    Answer: Stout
    
    
85. What seafood-serving Boston restaurant located near Faneuil Hall is located in a building from the early 1700s, is listed as a National Historic Landmark and has a reasonable claim as the oldest restaurant in Boston?
    
    Answer: Union Oyster House
    
    
86. Boston native David E. Kelley helmed the TV show Boston Public from 2000-2004, then what other "Boston" show from 2004-2008?
    
    Answer: Boston Legal
    
    
87. Boston is the capital of the commonwealth of Massachusetts. What other state or commonwealth capital city is the closest in distance to Boston?
    
    Answer: Providence
    
    
88. Rhett whined in shame in 2017 when Harvard scored their first Beanpot victory since 1993, over what school on the other side of the Charles?
    
    Answer: Boston University
    
    
89. "Boston Local Company" is the inspiration for the name of what local burrito bowl chain?
    
    Answer: Boloco
    
    
90. According to legend, how many lanterns were hung in the steeple of Boston's Old North Church during Paul Revere's midnight ride of 1775, in order to signal that the British were coming by sea?
    
    Answer: Two (One if by land, two if by sea)
    
    
91. Each year the legendary Boston Symphony Orchestra moves to its "summer home" at what venue in the Berkshires of western Massachusetts?
    
    Answer: Tanglewood
    
    
92. What NFC West team did the New England Patriots defeat on February 3, 2019 to become Super Bowl LIII champions?
    
    Answer: Los Angeles Rams
    
    
93. Which mile-long, walkable park that stretches from TD Garden to Chinatown was named after JFK’s mother?
    
    Answer: Rose Fitzgerald Kennedy Greenway
    
    
94. A bronze statue in Boston Public Garden depicts Mrs. Mallard and her eight offspring marching along a path, in homage to what classic children's picture book by Robert McCloskey?
    
    Answer: Make Way for Ducklings
    
    
95. What’s the name of the 3-mile pleasure walk you can take along the Charles River? (Hint: It’s similar to but not a promenade)
    
    Answer: Esplanade
    
    
96. What Somerville brewery has a name that means someone who pilots a hot-air balloon, airship, or other flying craft?
    
    Answer: Aeronaut
    
    
97. Josh Zakim, Mark Ciommo, Edward Flynn, and Andrea Campbell all share what title in the City of Boston's political system?
    
    Answer: City Councilor
    
    
98. What number did the Boston Red Sox retire in 2017 in honor of David Ortiz, a Dominican slugger who won three World Series during his tenure with the club from 2003 to 2016?
    
    Answer: 34
    
    
99. After the closing of Maria's in September 2019, there are now only two cannoli shops starting with the letter "M" in Boston's North End neighborhood that are considered "top tier" cannoli makers by magazines such as NewEngland.com and Eater. Name both of these longtime bakeries.
    
    Answer: Mike's and Modern
    
    
100. What professional sports team were previously named the Boston Pilgrims, Boston Somersets, and Boston Americans until they were officially given their present name in 1908 by team owner John I. Taylor?
     
     Answer: Boston Red Sox
     
     
101. The Museum of Fine Arts (MFA) in Boston is affiliated with the School of the Museum of Fine Arts at what university? Although the School of the Museum is located in Boston, the university's main campus is not.
     
     Answer: Tufts
     
     
102. The Wahlburgers TV series was, unsurprisingly, based on the chain of casual burger restaurants and bars named Wahlburgers. At least five family members featured prominently in the show, including actor Mark Wahlberg. Name any other member of the main cast with the last name Wahlberg.
     
     Answer: Donnie Paul Alma Brandon Bob
     
     
103. In 1959, what future dictator came to campus to such fanfare that he caused Harvard to move his speech to the football stadium for extra seating?
     
     Answer: Fidel Castro
     
     
104. What MBTA line gives its name to the ice hockey rivalry between Boston University and Boston College? It is also known as the Battle of Commonwealth Avenue.
     
     Answer: Green
     
     
105. Played by Dylan and Cole Sprouse, the title characters of what 2000s Disney Channel sitcom live at Boston's fictional Tipton Hotel, where their mom performs as a lounge singer?
     
     Answer: The Suite Life of Zack & Cody
     
     
106. What Boston burying ground, named for the type of building that stood where the Park Church now stands, contains the graves of Paul Revere, Samuel Adams, and John Hancock?
     
     Answer: Granary Burying Ground
     
     
107. Released in 2012, the third installment of what video game franchise, in which the titular group fights against the Templars, features scenes set in 18th-century Boston?
     
     Answer: Assassin's Creed
     
     
108. The fictional Boston neighborhood of "Buckingham Flats" is the setting of what award-winning 2003 film, named for a very real Boston-area waterway?
     
     Answer: Mystic River
     
     
109. There is a town of ~14,000 people in eastern Massachusetts that is home to the headquarters of EMC but is perhaps even more famous as the start of the Boston Marathon. What is this town?
     
     Answer: Hopkinton
     
     
110. Rosie Ruiz rose to fame in 1980 after she finished a running race in a record time of two hours and 31 minutes. However, the fame was mostly infamy as her title was stripped because of her lack of sweating, exhaustion, or knowledge of the course led to the natural conclusion that she had cheated. What was the race?
     
     Answer: Boston Marathon
     
     
111. The Boston Bruins last won the Stanley Cup in 2011, defeating what team that plays its home games more than 2,500 miles—and across a national border—from Boston?
     
     Answer: Vancouver Canucks
     
     
112. What sweet substance is guilty of a January 15, 1919 "flood" in which 21 people and several horses were killed in the North End?
     
     Answer: Molasses
     
     
113. Somerville is the fourth largest (by population) city in what Massachusetts county? Nearly one quarter of the state's population resides in this county.
     
     Answer: Middlesex County
     
     
114. What Boston-area super-chef rose to national prominence based on the reputation of restaurants called "Olives" and "Figs?"
     
     Answer: Todd English
     
     
115. On October 1, 1903, The Pittsburgh Pirates won the first World Series game over a team from what northeastern city? Unfortunately, the Pirates lost the Series.
     
     Answer: Boston
     
     
116. What American author, popularly known by a pseudonym, considered Hartford the most beautiful city in the United States and settled there to write what are considered his bildungsroman masterpieces? Coincidentally, this Missouri-born man lived next door to Harriet Beecher Stowe while in Hartford.
     
     Answer: Mark Twain
     
     
117. Harvard has more than enough bookshelves to stretch from their campus to what most populous city in New Hampshire?
     
     Answer: Manchester
     
     
118. In 2017, activists pressured what historic Boston marketplace to change its name, given its namesake's involvement in the slave trade?
     
     Answer: Faneuil Hall
     
     
119. In 2015 Boston opened a 1795 capsule from Sam Adams & what other man, including a silver plate he's thought to have made
     
     Answer: Paul Revere
     
     
120. Formerly known as the Mystic River Bridge, the cantilever truss bridge that spans more than two miles from Boston to Chelsea is the largest bridge in New England and was renamed in 1967 for what former Massachusetts governor?
     
     Answer: Tobin Bridge
     
     
121. At which Boston hospital is home to the Ether Dome, the location of the first public surgery done with the patient under anesthesia?
     
     Answer: Mass General
     
     
122. From 2015 to 2019, now-mayor Michelle Wu served on the Boston City Council with what woman, who later became the first Black woman elected to Congress from Massachusetts?
     
     Answer: Ayanna Pressley
     
     
123. Also the last name of some famous Hollywood brothers, what is the punny seven-letter name of the eagle mascot of Boston College's sports teams?
     
     Answer: Baldwin
     
     
124. What odd-numbered year was the only year of the 1960s in which the Boston Celtics did NOT win the NBA championship? (It was also the only year in that decade that the Boston Red Socks won the American League.)
     
     Answer: 1967
     
     
125. What Boston-based private equity investment firm was co-founded by former Massachusetts governor and current Utah Senator Mitt Romney?
     
     Answer: Bain Capital
     
     
126. What outdoorswear apparel company founded in Boston in 1952 is known mostly for its footwear? Its "Yellow Boot" collection has become a global pop culture icon.
     
     Answer: Timberland
     
     
127. When founded in 1906, this apparel company had a longer name that included the phrase "Arch Support Company," but the name has since been trimmed to only two words. What is this Boston-based manufacturer that famously features numbered product lines?
     
     Answer: New Balance
     
     
128. Which reservoir in Mass is the biggest, deepest lake in the state and supplies most of the Greater Boston area’s water?
     
     Answer: Quabbin
     
     
129. Not just a side dish, "Boston Baked Beans" are also a brand of confection that covers what legume in a sweet red candy coating?
     
     Answer: Peanut
     
     
130. Mary Barrett Dyer was a martyr that was hanged in Boston in 1660 because of her staunch commitment to what "friendly" religious group?
     
     Answer: The Quakers
     
     
131. Longtime Boston Celtics coach and executive Arnold Jacob Auerbach was a basketball pioneer who is credited with the invention of the fast break. Ironically, despite being associated with the Celtics, what was Auerbach's colorful nickname?
     
     Answer: Red Auerbach
     
     
132. The first public school in the United States was founded in 1635 in Boston. Despite its name, courses were largely taught in English. What was the name of this school?
     
     Answer: Boston Latin School
     
     
133. What robotics company, recently acquired by the Hyundai Motor Company, is known for making dynamic high-mobility robots and first commercialized one of their robots, Spot, in 2019?
     
     Answer: Boston Dynamics
     
     
134. "I've had dreams of Boston all my life" is a line from the 2008 song "Ladies of Cambridge" by what rock band with an undead creature in its name?
     
     Answer: Vampire Weekend
     
     
135. Mark Wahlberg plays a Boston native whose childhood wish made his toy bear come to life in what 2012 comedy film?
     
     Answer: Ted
     
     
136. In 2003, Siamak Taghaddos and David Hauser founded a Boston-based virtual phone system company that shares what name with a crème de menthe and crème de cacao cocktail?
     
     Answer: Grasshopper
     
     
137. What trail in Boston passes along 16 different foundational US historical sites through the city? It starts in Boston Common and ends up 2.5 miles later at Charlestown’s Bunker Hill monument.
     
     Answer: Freedom Trail
     
     
138. Named after a founding father (who may have been a brewer himself), what’s the official beer of the Boston Red Sox?
     
     Answer: Samuel Adams
     
     
139. Portland's two founders tossed a coin to decide whose home city to name the fledgling site after. Francis Pettygrove of Portland, Maine won the toss, but which New England capital would have been used as the name if Asa Lovejoy had won?
     
     Answer: Boston
     
     
140. What left-handed pitcher started the first World Series game in Colorado Rockies history? In this case, the first time was not a charm, as he gave up 6 runs in only 4 innings against the Boston Red Sox.
     
     Answer: Jeff Francis
     
     
141. What is the name of the Major League Soccer team based in the Greater Boston area?
     
     Answer: New England Revolution
     
     
142. What Major League Baseball team won the 1914 World Series while in Boston, before moving to Milwaukee in 1953, and then further south in 1966, where they play today?
     
     Answer: Braves
     
     
143. The first mutual fund in the U.S. came courtesy of a lawyer named Edward Crosby Johnson II, who went on to found what financial corp based in Boston that now offers more than 500 mutual funds?
     
     Answer: Fidelity
     
     
144. What historic bookstore and Boston landmark, which became a meeting place for writers like Henry Wadsworth Longfellow, Ralph Waldo Emerson, and Henry David Thoreau, has been called the "Cradle of American Literature?"
     
     Answer: Old Corner Bookstore
     
     
145. An infamous and anonymous busker, often seen in Boston's T stations and public parks, wears a bear costume and plays what electronic instrument?
     
     Answer: Keytar
     
     
146. The fourth installment of what popular video game series takes place in a post-apocalyptic Boston, allowing players to explore eerie icons like Bunker Hill and Independence Hall?
     
     Answer: Fallout
     
     
147. Based in Boston, Massachusetts and founded in 2017, what IT company which involves databases has an animal for a name?
     
     Answer: Jellyfish
     
     
148. What famed Boston author of "Little Women" was previously taught by Henry David Thoreau and even penned him a poem titled "Thoreau's Flute?"?
     
     Answer: Louisa May Alcott
     
     
149. Metro Boston has long featured a large number of Americans who trace their ancestry to the Dominican Republic, and in the 2000s, this group passed what other Hispanic group as the most populous Hispanic group in the region?
     
     Answer: Puerto Rican Americans
     
     
150. What Nabisco-produced snack cookie with mostly yellow packaging was named for a town near Boston?
     
     Answer: Fig Newton
     
     
151. What New England-born poet was famously prolific, but having written nearly 1,800 poems had fewer than a dozen published during her lifetime? Famous poems include "Because I could not stop for Death" and "Tell all the truth but tell it slant."
     
     Answer: Emily Dickinson
     
     
152. Known as a controller of more destructive garden pests, what bug is the official insect of Delaware and Massachusetts?
     
     Answer: Ladybug
     
     
153. Featuring an eponymous IPA, a series of "UFO" beers, and myriad seasonal beers, what Boston brewery was founded in 1986 and expanded to a second location in Vermont in 2000?
     
     Answer: Harpoon
     
     
154. What Austrian-born composer, known as the "father of modern music" for his pioneering use of twelve-tone technique, emigrated in 1933 to Boston and then to Los Angeles to escape Nazi persecution?
     
     Answer: Arnold Schoenberg
     
     
155. In April 2004, Tom Brush and his friend and F. Hererra opened a taqueria in Harvard Square. What is the name of this mainstay on Brattle Street?
     
     Answer: Felipe's Taqueria
     
     
156. A soft, buttery style of dinner roll is named after what historic Boston hotel, where it's said they were invented in the late 19th century?
     
     Answer: Parker House
     
     
157. Which poet’s headstone in Amherst’s West Cemetery has “Called back” as its epitaph? (Hint: She once wrote: “Because I could not stop for Death, he kindly stopped for me.”)
     
     Answer: Emily Dickinson
     
     
158. Despite poor reviews and even poorer performance at the box office, what 1999 movie set in Boston (though mostly filmed in Toronto) followed fraternal twins turned vigilante killers became a cult favorite in part due to an exclusive partnership with Blockbuster?
     
     Answer: The Boondock Saints
     
     
159. There are 50 state capitals. Let's rank them by population size. What number is Boston? In this case, 1 is the most populous U.S. state capital and 50 is the least populous.
     
     Answer: 6
     
     
160. I-90, the longest interstate highway in the United States, has its termini in Boston and what west coast city (which is NOT its state's capital)?
     
     Answer: Seattle
     
     
161. What “V” biotech startup, started in Boston in 2011, is working on a platform of stability to allow for global delivery of vaccines? Their name is fittingly a spin on a shorthand of the word “vaccine.”
     
     Answer: Vaxess Technologies
     
     
162. Located at 46 Joy St in Boston's Beacon Hill neighborhood, what museum was opened in 1972 after previously serving as a Baptist Church, meeting hall, and synagogue in its more than 200-year history?
     
     Answer: Museum of African American History
     
     
163. In June of what year did the Boston Celtics win their 17th (and most recent) NBA Finals?
     
     Answer: 2008
     
     
164. Located in Charlestown and opened in 1780, what Boston tavern is often said to be the oldest watering hole in the state of Massachusetts? George Washington and Paul Revere were both known to frequent the spot.
     
     Answer: The Warren Tavern
     
     
165. From 1980 to 1993, what five-time Oscar winner served as conductor of the Boston Pops Orchestra?
     
     Answer: John Williams
     
     
166. What is the name of the first public school in the United States which was founded in Boston in 1635?
     
     Answer: Boston Latin School
     
     
167. What is the name of the oldest producer of chocolate in the U.S.? The company was founded in Boston in 1765 and is still in operation. Coincidentally, the company's name came from its founder's surname, but it is still quite appropriate for the food industry.
     
     Answer: The Baker Chocolate Company
     
     
168. In the 19th and early 20th centuries in America, what two-word term was used to describe two women living together without financial support from a man -- often, but not always, a lesbian partnership?
     
     Answer: Boston marriage
     
     
169. What movie, based on a TV show from the 1980's, features Denzel Washington as a Boston intelligence officer who protects a teenager from the Russian mafia?
     
     Answer: The Equalizer
     
     
170. What band behind the 1990 hit "Poison" took their name from their three founding members, who themselves spun off of the Roxbury-based R&B band New Edition?
     
     Answer: Bell Biv DeVoe
     
     
171. Charles H. Taylor is one of six businessmen that founded a company in 1872 which has continued to exist until the present day in Boston. The company was purchased in 2013 by Boston Red Sox and Liverpool F.C. owner John W. Henry for $70 million. What is the company?
     
     Answer: The Boston Globe
     
     
172. A young woman from the Boston suburbs gets a glamorous internship in New York City in what 1963 novel, the only one Sylvia Plath completed?
     
     Answer: The Bell Jar
     
     
173. What is the name of the Major League Soccer club that plays its home games in Foxborough's Gillette Stadium?
     
     Answer: Revolution
     
     
174. On his second time playing "Survivor," contestant "Boston Rob" Mariano fell in love with what fellow contestant, whom he eventually proposed to on the finale episode of the show's eighth season?
     
     Answer: Amber
     
     
175. Due to the celebration's pagan ties, Boston's Puritans banned what event from 1659-1681?
     
     Answer: Christmas
     
     
176. The Plaque to the Great Elm tree, Robert Gould Shaw Memorial, Soldiers and Sailors Monument, and Boston Massacre Memorial are all located within what Boston institution?
     
     Answer: The Boston Commons
     
     
177. What year was the Pru(dential Tower) completed on Boylston Street?
     
     Answer: 1964
     
     
178. If every Welch’s juice or jelly commercial is to be believed, which grape cultivar invented by Boston native Ephraim Wales Bull simply can't be beat?
     
     Answer: Concord
     
     
179. There are dents on Harvard sidewalks that are believed to be from what thing, thrown from dorm rooms during the Revolutionary War?
     
     Answer: Cannonballs
     
     
180. Which Boston neighborhood used to be called the “garden suburb” of the city and was part of Roxbury, but today is home to the Birch St. Plaza and a Farmer’s Market at Adams Park?
     
     Answer: Roslindale
     
     
181. In February 2023, Prince William and Princess Catherine of the UK visited Beantown, including a walk on a chilly and windy day through what alliteratively named park in East Boston?
     
     Answer: Piers Park
     
     
182. What is the name of the security company founded in 2006 by two Harvard Business School students who couldn't find a security company designed to help renters? The couple was interested in the field after multiple friends in Cambridge had experienced break-ins. By 2014, the company has raised more than $50 million in venture capital.
     
     Answer: Simplisafe
     
     
183. Harry Frazee held what powerful, recognizable Boston role from 1916-1923?
     
     Answer: Owner of the Red Sox
     
     
184. Government Center in Boston is built on the former site of what city square? The square is mentioned in the Kingston Trio song "MTA" — it is the station where Charlie's wife hands him a sandwich every day.
     
     Answer: Scollay
     
     
185. Set just before the American Revolution, what Newbery-winning Esther Forbes novel's title character is a silversmith's apprentice who takes part in the Boston Tea Party?
     
     Answer: Johnny Tremain
     
     
186. The Black Heritage Trail is a 1.6-mile walking tour exploring the history of Boston's 1800s Black community who primarily lived on the northern portion of what neighborhood?
     
     Answer: Beacon Hill
     
     
187. Boston College was in what athletic conference before joining the Atlantic Coast Conference (ACC) in 2005?
     
     Answer: Big East
     
     
188. Which serial killer claimed 11 female victims between 1962 and 1964 before he was eventually identified as Albert DeSalvo?
     
     Answer: The Boston Strangler
     
     
189. Located at 11 Marshall Street, what "colorful" Boston bar is named after an older, now-demolished pub where the Sons of Liberty met during the American Revolution?
     
     Answer: The Green Dragon
     
     
190. Based on the average high temperature over the course of the past 100 years, what is the coldest month of the year in Boston?
     
     Answer: January (36 degrees Fahrenheit as average high temp)
     
     
191. Historical reenactments, Freedom Trail walks, live music, and boat tours are part of what festival that takes place annually in Boston during the week of Independence Day?
     
     Answer: Harborfest
     
     
192. In Holyoke, Massachusetts in 1895, William Morgan created a new game called Mintonette which was an indoor activity taking some characteristics from tennis and handball. Coincidentally, basketball had been invented ten miles away only four years prior. What sport did Morgan invent?
     
     Answer: Volleyball
     
     
193. Named for a gummy candy, what Asian-American Boston drag queen is a fan favorite who has appeared on the third regular season as well as All-Stars Seasons 1 and 5 of "RuPaul's Drag Race?"
     
     Answer: Jujubee
     
     
194. In an early example of the relationship between beer and sports, in 1945 Narragansett Beer sponsored the first televised games of what American League baseball team?
     
     Answer: Boston Red Sox
     
     
195. What South Boston bar, which claims to have the oldest hand-carved bar in America, has a name that implies it's located along Germany's Rhine River?
     
     Answer: Amrheins
     
     
196. What Unitarian church, located at Tremont and Stone Streets, has served Bostonians since 1754?
     
     Answer: King's Chapel
     
     
197. What term was first coined by physician and writer Oliver Wendell Holmes and is typically used to refer to a group of 50+ "elite" families of Boston often associated with Harvard, Anglicanism, and high social and economic standing?
     
     Answer: Boston Brahmins
     
     
198. AMT is the stock ticker for what Boston-based Fortune 500 company that is both a real estate investment trust and owner-operator of wireless and broadcast communications infrastructure in several countries worldwide?
     
     Answer: American Tower
     
     
199. What legendary Japanese-born conductor served as music director of the Boston Symphony Orchestra from 1973 to 2002?
     
     Answer: Seiji Ozawa
     
     
200. The oldest continually performing choral and instrumental society is located in Boston, named after George Frideric Handel and what other 18th-century composer? This composer has sometimes been called "the Father of the Symphony."
     
     Answer: Haydn
     
     
201. What TV drama that aired 2000-04 centered on a fictional public high school in Boston named Winslow High School and featured a large ensemble cast of teachers, students, and administrators?
     
     Answer: Boston Public
     
     
202. What famous David was a legendary Designated Hitter and 1st Baseman for the Boston Red Sox, ending his career with 541 home runs and famous postseason moments during his three MLB championships, in 2004, 2007, and 2013?
     
     Answer: David Ortiz
     
     
203. What co-founder of the NAACP was also the first African American to earn a doctorate at Harvard?
     
     Answer: W. E. B. Du Bois
     
     
204. Former President George H.W. Bush was born in what affluent Boston suburb in 1924?
     
     Answer: Milton
     
     
205. The Trail Blazers had the longest streak of consecutive sold-out home games within the "Big 4" American sports leagues until what East Coast MLB team surpassed them in 2013?
     
     Answer: Boston Red Sox
     
     
206. Every October, over 11,000 rowers come to Boston for the biggest 2-day event of its kind in the world. The course starts at the DeWolfe Boathouse and goes 3 miles to the Henderson Boathouse. Casually known by its acronym, HOCR, what is the event officially called?
     
     Answer: Head of the Charles Regatta
     
     
207. Which ice cream shop on Cambridge Street is known for its array of interesting flavors for its homemade scoops, like burnt sugar, carrot cake, ginger molasses, and coffee Oreo?
     
     Answer: Christina's
     
     
208. The Computer Museum opened in 1979 and operated in three different locations until 1999. It closed in 2000 and sent much of its collection across the country to the Computer History Museum in California. In what city would you have found the Computer Museum while it was open?
     
     Answer: Boston
     
     
209. Harvard's Warren Anatomical Museum displays the fractured skull of what man, who became famous as a scientific subject after an iron rod was driven through his brain in a railroad accident?
     
     Answer: Phineas Gage
     
     
210. What Beacon Hill institution, one of the oldest independent lending libraries in the United States, was founded in 1807 by members of the Boston Anthology Society?
     
     Answer: Boston Athenaeum
     
     
211. What mixed-race Black and Native American man who escaped slavery is generally regarded to be the first American colonist killed in the Boston Massacre, and thereby the first American to die in the Revolution?
     
     Answer: Crispus Attucks
     
     
212. Boston is of course the capital Massachusetts, but it is also the name of a town in England which was home to several of the prominent first settlers of the American Boston. In what "presidential" English county is the UK's Boston located?
     
     Answer: Lincolnshire
     
     
213. There are two telephone area codes that serve the Boston area. There was only one for decades until the second was overlaid on top of the first in 2001 as more auxiliary devices such as fax machines required phone numbers. Name BOTH of these area codes.
     
     Answer: 617 and 857
     
     
214. Which saloon in Somerville is the place to go if you want some craft beer and a burger and/or a corned beef hash brisket sandwich?
     
     Answer: Olde Magoun's Saloon
     
     
215. The MBTA subway in the Boston metropolitan area is the oldest subway still-operating in the US. Of the 133 stations in the system, how many are located underground?
     
     Answer: 26
     
     
216. "Boston Hymn" is a 19th-century poem by what American thinker also known for his essays like "Nature" and "Self-Reliance?"
     
     Answer: Ralph Waldo Emerson
     
     
217. What Boston neighborhood was home to Sylvia Plath, Robert Frost, and Louisa May Alcott for portions of their lives? Alcott published her first story while living in the neighborhood while Plath and Frost lived here later in life.
     
     Answer: Beacon Hill
     
     
218. A rehab facility in suburban Boston is one of the primary settings of what nearly 1,100-page 1996 novel by David Foster Wallace?
     
     Answer: Infinite Jest
     
     
219. What Boston-area school has a total of around 10,000 students, is the eighth largest university in Metro Boston, and was initially founded in 1906 as "Archer's Evening Law School," with an original goal to "serve ambitious young men who are obliged to work for a living while studying law?"
     
     Answer: Suffolk University
     
     
220. What's the name of the three-story tall stained-glass globe that is the main attraction of Boston's Mary Baker Eddy Library, which also houses the papers of the namesake founder of the Christian Science Movement?
     
     Answer: The Mapparium
     
     
221. In the Boston-centric 2010 film "The Town," what actress plays the bank manager taken hostage by the group of bank-robbing protagonists?
     
     Answer: Rebecca Hall
     
     
222. Jamaica Pond is Boston's largest body of freshwater. It's a kind of lake formed by a retreating glacier known by what name, which it shares with an object you might find in your kitchen?
     
     Answer: Kettle Lake
     
     
223. Rockledge is the name of a Roxbury Heights estate once owned by what notable abolitionist and publisher of The Liberator?
     
     Answer: William Lloyd Garrison
     
     
224. Jill Hennessy played Dr. Jordan Cavanaugh, a Boston forensic medical examiner, on what NBC drama that aired from 2001 to 2007?
     
     Answer: Crossing Jordan
     
     
225. Hosted by the paper's advice columnist Meredith Goldstein, "Love Letters" is a podcast with four seasons (and counting) about love and relationships and produced by what newspaper?
     
     Answer: The Boston Globe
     
     
226. The sixth American woman to be granted the rank of Papal countess received this honor in 1951 from Pope Pius XII. Who was this Boston-born woman?
     
     Answer: Rose Fitzgerald Kennedy
     
     
227. What critically acclaimed alternative rock band was founded in Boston in 1986, featured bassist Kim Deal, and disbanded acrimoniously in 1993?
     
     Answer: The Pixies
     
     
228. Due to the compact design and high population density, Boston's neighboring city Cambridge often ranks as #1 in the U.S. in the category of highest share of residents that use what form of transportation to commute to work?
     
     Answer: Walking
     
     
229. "Boston Legal," which ran from 2004 to 2008, is a spinoff of what earlier David E. Kelley legal series?
     
     Answer: The Practice
     
     
230. What is the name of the bridge that crosses the Charles River and connects the Harvard campuses in Cambridge and Boston (its Allston neighborhood, specifically)?
     
     Answer: John W. Weeks Bridge
     
     
231. Harvard's well-known for its Cambridge campus but also its Allston and Longwood facilities in the Boston area which largely focus MBA and MD programs, respectively. In what other Massachusetts town would you find the Harvard Forest? This area is a 3,000-acre ecological research forest that is open to the public.
     
     Answer: Petersham
     
     
232. Although they had a slightly different name at the time, Harvard Stadium was the home stadium of the New England Patriots for a single NFL season. In what decade was this?
     
     Answer: 1970s
     
     
233. The Battle of Bunker Hill in Boston was one of the turning points of the American Revolutionary War. Today, you can visit the monument as well as climb the 221-foot granite obelisk which honors the fallen soldiers. How many steps does it take to climb to the top?
     
     Answer: 294
     
     
234. What charismatic harbor seal, raised by humans and the subject of a 1994 movie, lived during the winters at the Boston Aquarium before swimming back to Maine every summer?
     
     Answer: Andre
     
     
235. The oldest continuously running community theatre group in the U.S. is the Footlight Club in Boston, having performed every year since 1877. In what neighborhood will you find this non-profit? The street address of club headquarters is 7 Eliot St.
     
     Answer: Jamaica Plain
     
     
236. Born in Cambridgeport, MA, the first full-time American female book reviewer in journalism wrote "Woman in the Nineteenth Century" which is often considered the first major feminist work in the United States. Who was this native New Englander?
     
     Answer: Margaret Fuller
     
     
237. "The Bostonians" is a late-19th-century novel by what American author who is also known for "Daisy Miller" and "The Portrait of a Lady?"
     
     Answer: Henry James
     
     
238. Used from around 2000 until its retirement in 2018, the Boston Red Sox' much-discussed analytics system was called what—an appropriate name, as it is a shade of red?
     
     Answer: Carmine
     
     
239. What farm in present-day West Roxbury, led by George and Sophia Ripley, was perhaps the most prominent utopian community in the 19th century U.S.?
     
     Answer: Brook Farm
     
     
240. Six letters, starts with an N: Among crossword enthusiasts, what suburb of Boston has become synonymous with an obscure answer in a puzzle that is crossing another hard-to-figure-out answer?
     
     Answer: Natick
     
     
241. What band recorded the song "Roadrunner," a 1976 ode to Massachusetts Route 128 in Boston's suburbs, and which some lawmakers have proposed to make the state's official rock song?
     
     Answer: The Modern Lovers
     
     
242. In 2007, a number of mysterious blinking electronic signs caused multiple bomb scares in the Boston area. The signs, meant as a guerilla marketing tactic, depicted the Mooninites from what Adult Swim cartoon?
     
     Answer: Aqua Teen Hunger Force
     
     
243. What was the only number one hit for the band Boston, who, as you might expect, hails from Boston, MA?
     
     Answer: Amanda
     
     
244. Although it has been closed for over 70 years because of enhanced fire codes enacted in the 1940s, there is an underground concert venue on Boston's famed "piano row." This venue shares its name and building with what well-known piano maker?
     
     Answer: Steinert
     

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