79 Massachusetts Trivia Questions (Ranked from Easiest to Hardest)

Updated Date:
August 29, 2025
Which companies play trivia with their co-workers every week?
lyft logo
amazon logoimpossible logo

Are you a history buff looking to test your knowledge of Massachusetts? Or perhaps you're a trivia enthusiast looking for a new challenge?

Look no further than Massachusetts trivia questions! Known as the "Bay State," Massachusetts is located in the northeastern region of the United States and has a rich history dating back to its founding by the Pilgrims in 1620. As one of the oldest states in the country, it played a crucial role in the American Revolution, with iconic events such as the Boston Tea Party and the Battle of Lexington and Concord taking place within its borders.

Famous figures like Paul Revere, Samuel Adams, and John Adams also call Massachusetts home. With diverse geography ranging from the Atlantic coast to the Berkshire Mountains and renowned universities like Harvard and MIT, there's no shortage of fascinating facts to learn about this state. From its role in shaping American history to its delicious seafood, particularly Boston Clam Chowder, Massachusetts trivia questions offer a fun and educational way to explore all that this state has to offer.

79 Massachusetts Trivia Questions Ranked From Easiest to Hardest (Updated for 2025)

1. Canadian-American physical educator James K. Naismith famously invented what sport while working at a YMCA school in Springfield, Massachusetts?

Answer: Basketball


2. Before a career in politics that would include stints as governor (Massachusetts), senator (Utah), and Republican presidential hopeful, what American politician co-founded and consulted for Bain Capital?

Answer: Mitt Romney


3. Inspired by a long-distance event in the 1896 Summer Olympics, what famous American race takes place annually in Massachusetts in April on Patriots' Day?

Answer: Boston Marathon


4. Although James Naismith was teaching in Massachusetts when he invented a popular sport, he was a native Canadian who had only recently moved to the U.S. What sport did Naismith invent in 1891?

Answer: Basketball


5. In response to a question about pay equity during a 2012 presidential debate, Mitt Romney stated that when filling his cabinet as governor of Massachusetts, women's political group MassGAP sent him nearly 200 résumés of female candidates, which Romney clumsily described with what four-word phrase?

Answer: Binders full of women


6. After graduating from Harvard, Mitt Romney worked for a management consulting group named after what New England city, the capital of the state he eventually became governor of?

Answer: Boston


7. In 1878, Scotsman James Edgar set up a dry goods store on Main Street in Brockton, Massachusetts. Twelve years later, looking to drum up more business at the store, he dressed up as what giving character?

Answer: Santa Claus


8. The Cape Wind project was a proposed offshore wind farm off which East Coast state that got approved but never moved forward because of legal hangups and debate?

Answer: Massachusetts


9. 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


10. When the United States Board on Geographic Names worked to standardize place name spellings in the late 19th century, apostrophes were dropped. Now known for being home to the Obamas more than grapes, it took until the early 20th century for what Massachusetts island to regain the moniker that exists today?

Answer: Martha's Vineyard


11. In 1999, what women's liberal arts college in Cambridge, Massachusetts, officially consolidated with Harvard to become one and the same?

Answer: Radcliffe College


12. In 2018, which New England state came in higher than the other U.S. states on the Human Development Index (HDI)?

Answer: Massachusetts


13. 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


14. The Halloween classic "Hocus Pocus" is set in what guessable Massachusetts city?

Answer: Salem


15. Henry David Thoreau wrote about life in the woods in Massachusetts in what iconic 1854 work of nonfiction literature?

Answer: Walden


16. 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


17. What famed Massachusetts act traditionally performs on the Esplanade every Fourth of July?

Answer: Boston Pops


18. Unlike co-founders Filip Kaliszan, James Ren, and Benjamin Bercovitz, who went to Stanford, chairman and co-founder Hans Robertson received undergrad and master's degrees from what East Coast university?

Answer: MIT


19. One of IQVIA's largest competitors in the CRO space is a Wilmington, Massachusetts-based company that trades on the New York Stock Exchange under CRL, and is named for what nearby waterway?

Answer: Charles River


20. Not to be outdone by second cousin and second U.S. President John, what was the name of the founding father who was a delegate to the Continental Congress and 4th governor of Massachusetts?

Answer: Sam Adams


21. The Massachusetts Institute of Technology (MIT) is the majority owner of what manufacturing company that predominantly sells audio equipment? The company was founded by an associate professor who later in life donated his shares to the school.

Answer: Bose


22. Appropriate 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


23. 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


24. The chocolate chip cookie was invented in 1938 by Ruth Wakefield, the proprietor of what Massachusetts inn, which gave its name to the Nestlé brand and cookbook that popularized them?

Answer: The Toll House Inn


25. What company, started in South Grafton, Massachusetts, and named after its founder, has become world famous for plastic containers, plates, bowls, and other household items?

Answer: Tupperware


26. Each year, the legendary Boston Symphony Orchestra moves to its "summer home" at what venue in the Berkshires of western Massachusetts?

Answer: Tanglewood


27. In which New England state are real estate brokers not required to tell prospective home buyers if a house is haunted?

Answer: Massachusetts


28. The hourglass-shaped pour-over coffeemaker produced by what Massachusetts-based company was named "one of the best-designed products of modern times" and is included in the collection of the Museum of Modern Art?

Answer: Chemex


29. 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


30. Transcendentalist writer Henry David Thoreau spent two years in solitude near what pond in Concord, Massachusetts, which also serves as the name of the book he wrote about his experiences there?

Answer: Walden


31. 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


32. 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


33. What Boston-based private equity investment firm was co-founded by former Massachusetts governor and current Utah Senator Mitt Romney?

Answer: Bain Capital


34. Erected between 1718 and 1720, what is the oldest building on Harvard's campus?

Answer: Massachusetts Hall


35. General Electric was formed in 1892 when the Edison General Electric Company and the Thomson-Houston Electric Company merged. Which two states served as headquarters for Edison and Thomson-Houston?

Answer: New York and Massachusetts


36. Which reservoir in Mass is the biggest, deepest lake in the state and supplies most of the Greater Boston area’s water?

Answer: Quabbin


37. Although they're separated by nearly 3,000 miles, Caltech, the famous university in Pasadena, enjoys a lively, prank-filled rivalry with what equally prestigious New England school?

Answer: Massachusetts Institute of Technology


38. In 1701, Massachusetts passed laws for ship quarantine and patient isolation for the management of what disease, a now eradicated virus also known as variola?

Answer: Smallpox


39. What “N” food brand, founded in 1978 in Massachusetts, is the most popular brand of tofu in the United States? They were acquired by Pulmuone Foods in 2016.

Answer: Nasoya


40. In 1649, Sarah Norman and Mary Hammon were the first women in the U.S. convicted of lesbian behavior in the American colonies, being convicted in what Massachusetts town famous for a rock that was a pilgrim landing site?

Answer: Plymouth


41. In 2004, Massachusetts became the first state to legalize same-sex marriage, but it took four years until a second state followed sui. Which non-New England state was it?

Answer: California


42. Opened in 1934, which spot in Cape Cod is one of the oldest places to grab a homemade ice cream cone in New England?

Answer: Four Seas Ice Cream


43. What 2000 film described the loss of the Gloucester, Massachusetts-based fishing vessel Andrea Gail in the titular weather event?

Answer: The Perfect Storm


44. Gerry Studds came out following a scandal in which he had a sexual relationship with a 17-year-old page, thus becoming the first openly gay member of the U.S. Congress. What state was his district in?

Answer: Massachusetts


45. Although it's supposedly set in Massachusetts, what classic 1998 "spooky season" movie was actually filmed in the charming small town of Coupeville on Washington's Whidbey Island?

Answer: Practical Magic


46. Based in Boston, Massachusetts, and founded in 2017, what IT company that involves databases has an animal for a name?

Answer: Jellyfish


47. What K term is for an authentication system developed at the Massachusetts Institute of Technology (MIT), which enables the exchange of private information across an open network by assigning a unique key called a "ticket" to a user requesting access to secure information?

Answer: Kerberos


48. The University of Massachusetts Boston, the John F. Kennedy Museum and Presidential Library, and the Edward M. Kennedy Institute for the United States Senate can all be found in what Boston neighborhood?

Answer: Columbia Point


49. Between February 1692 and May 1693, the infamous prosecutions and hearings of the Salem witch trials were held in what New England U.S. state?

Answer: Massachusetts


50. What Massachusetts town, home to Smith College, was named "Lesbianville, U.S.A." by the National Enquirer in 1992 and remains a popular countercultural hub for LGBTQ+ people in the Northeast?

Answer: Northampton


51. If you bake a batch of chocolate cookies using Nestle morsels, chances are you're using the recipe invented at what Massachusetts restaurant, which is found on the back of the package?

Answer: Toll House Inn


52. Harvard Forest, a 4,000-acre ecological research area and one of the oldest managed forests in the U.S., is located in what central Massachusetts town?

Answer: Petersham


53. Harvard isn't just in Massachusetts, David. It owns several libraries and research centers around the world, including the Villa i Tatti located in what Italian city?

Answer: Florence


54. Massachusetts Hall has a long and varied history as Harvard’s oldest building. For example, in 1722, it served as an observatory after Thomas Hollis donated a 24-foot-tall object used to view the night sky to the school. What was his massive gift?

Answer: Telescope


55. Matt Groening says it’s not Massachusetts or Illinois but just an Anytown USA location that inspired what “Simpsons” city?

Answer: Springfield


56. In “Jaws” the book, Amity was located on the west end of Long Island about twenty minutes from Sag Harbor. When it came to filming the movie, the producers selected what other somewhat nearby Massachusetts island that ironically produces almost no wine?

Answer: Martha's Vineyard


57. The first chocolate manufacturer started its business in 1765, on the banks of the Neponset River, in what New England state?

Answer: Massachusetts


58. Known as a controller of more destructive garden pests, what bug is the official insect of Delaware and Massachusetts?

Answer: Ladybug


59. From 2015 to 2019, 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


60. On May 17, 2004, Marcia Kadish and Tanya McCloskey became the first legally married same-sex partners in the United States when they were wed in which state (the first to legally recognize same-sex marriage)?

Answer: Massachusetts


61. Popularly known for taking his infamous photo-op aboard an M1 Abrams tank, Michael Dukakis served as the governor of which U.S. state during the 1970s and 1980s prior to his 1988 presidential campaign?

Answer: Massachusetts


62. Somerville is the fourth largest (by population) city in what Massachusetts county? Nearly one quarter of the state's population resides there.

Answer: Middlesex County


63. A 1970 speech given by the Native American activist Frank "Wamsutta" James in Plymouth, Massachusetts marked the inaugural National Day of Mourning demonstration. On what important day in the American calendar does this demonstration take place annually?

Answer: Thanksgiving


64. What bus company began in Massachusetts in 1933, with just two Buick limousines, and was named for the founder's son's favorite children's book?

Answer: Peter Pan Bus Lines


65. Katharine Lee Bates, a Massachusetts woman who lived in a "Boston marriage" with her partner Katharine Coman until her death in 1929, is best remembered for writing what patriotic song, inspired by a trip to Colorado?

Answer: America the Beautiful


66. Huckle Cat, Lowly Worm, and Sprout Goat are some of the various characters who can be found within the busy world of what Massachusetts-born author and illustrator?

Answer: Richard Scarry


67. 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


68. What Northeastern U.S. state provides a base for the commercial fishermen on the reality television show "Wicked Tuna"?

Answer: Massachusetts


69. Although its sports teams are named the Judges, what Massachusetts university named for a former Supreme Court Justice has a mascot named Ollie the Owl?

Answer: Brandeis University


70. Established in 1924, MFS is one of the oldest investment firms in the USA. What does MFS stand for?

Answer: Massachusetts Financial Services


71. During a period of rapid early growth at Nike in the mid-1960s, the company's first East Coast retail location was opened in what Massachusetts town?

Answer: Wellesley


72. In what Northeastern city was the first large free municipal library in the U.S. founded in 1848?

Answer: Boston


73. 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


74. Boston is, of course, the capital of 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 Boston, located in the UK?

Answer: Lincolnshire


75. Mary Whiton Calkins was the first female president of the American Psychological Association and famously conducted research on dreams and memory after being taught by William James. At what Massachusetts school did Calkins teach for many years? The school shares its name with the city in which it is located.

Answer: Wellesley College


76. Harvard's well-known for its Cambridge campus but also its Allston and Longwood facilities in the Boston area, which largely focus on 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


77. Which Massachusetts-based startup created an app and e-learning platform that uses a marketplace model to connect 50,000 language tutors with over 100,000 learners?

Answer: Preply


78. 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


79. A National Historic Site in Brookline, Massachusetts is named for what landscape architect? It was the site of the world's first full-scale professional office for the practice of landscape design.

Answer: Olmsted

Play Massachusetts Trivia with Water Cooler Trivia

Water Cooler Trivia is well-equipped to provide you with exciting and engaging trivia quizzes.

So, how does it work?

Each week, our team will deliver original trivia quizzes straight to your inbox.

All you have to do is pick the categories.

You can leave the rest of the heavy lifting to us.

Take Water Cooler Trivia for a test run with our four-week free trial.

Is there an error in one of our questions?

We do everything we can to ensure that Water Cooler Trivia's questions are appropriate, relevant, and accurate. Our database has tens of thousands of questions, so we don't always get it right. If you see a question that needs editing, we would love if you let us know here or email [email protected].

Celebrating brains
1,200 companies play Water Cooler Trivia every week
Learn MoreWeekly Trivia For Your Office →