Massachusetts is a state rich in history, culture, and natural beauty. From the cobblestone streets of Boston to the mountains of the Berkshires, the Bay State has inspired artists, authors, and intellectuals for centuries. This article features 55 riddles that explore different aspects of Massachusetts, from its colonial past to its sports teams, landmarks, and more. Test your knowledge of the Commonwealth with these brain teasers! The answers to each riddle follow in the subsequent paragraphs. Enjoy this challenging game and learn some new facts about Massachusetts along the way.
The Riddles
1. I’m a body of water found between Cape Ann and Cape Cod. Sailboats love sailing my waters on sunny summer days. What am I?
2. I’m an Ivy League university located along the Charles River in Cambridge. My notable alumni include John F. Kennedy and Mark Zuckerberg. What am I?
3. I’m a tall granite tower that commemorates the Battle of Bunker Hill. You can climb my294 steps for beautiful views of Boston. What am I?
4. I’m an elite prep school in Andover. My famous alumni include both George Bush presidents. What am I?
5. I’m a type of creamy clam chowder that is synonymous with Boston. What am I?
6. I’m a posh Boston neighborhood known for my brick row houses. Authors like Louisa May Alcott once lived on my streets. What neighborhood am I?
7. I’m a tragic maritime disaster that involved a steamship colliding with an iceberg in 1912 near Cape Cod. What am I?
8. I’m an NFL team that plays in Foxborough. Our quarterback Tom Brady has won six Super Bowls. Who are we?
9. I’m a popular bean-shaped tourist site located in Boston Common. Visitors love climbing all over me. What am I?
10. I’m a historic university in Williamstown founded in 1793. Our notable alumni include James A. Garfield and Cole Porter. What university am I?
11. I’m a writer from Concord who authored classic books like Walden and Civil Disobedience. Who am I?
12. I’m an artistic colony located in the Berkshires. Here you’ll find the summer homes of authors like Edith Wharton. What am I?
13. I’m a breakfast dish consisting of baked beans, eggs, and brown bread. I’m a specialty in Boston. What am I?
14. I’m a Cape Cod town famous for its artist shanties and beaches like Coast Guard Beach. What town am I?
15. I’m a chocolate sandwich cookie invented in Newton. I’m made by Nabisco. What am I?
16. I’m a street in Boston where you can visit Faneuil Hall and Quincy Market. What street am I?
17. I’m the first public park created in America, located right in the heart of Boston. What am I?
18. I’m a city southwest of Boston recognized as the birthplace of the Industrial Revolution. What city am I?
19. I’m a Catholic university in Worcester known for our Holy Cross sports teams. What’s my name?
20. I’m a popular summer retreat island located off Cape Cod. Former President Obama vacations here. What island am I?
21. I’m a private men’s liberal arts college located in Williamstown next door to an art museum. What college am I?
22. I’m an NFL team that plays in Foxborough along with the Patriots. Our mascot is Pat Patriot. Who are we?
23. I’m a cape located on the northernmost tip of Massachusetts. I’m home to Motif Number 1, the most painted building in America. What cape am I?
24. I’m a historic state located near Boston where you can visit Plimoth Plantation. What state am I?
25. I’m a classy department store founded in Boston where you can shop while drinking tea in the dining room. What store am I?
26. I’m a town near Cape Cod known for its glass-blowing studios and beautiful beaches like Sandy Neck Beach. What town am I?
27. I’m a tasty codfish dish traditionally made with salt cod, cream, and crackers. I’m a classic New England dish. What am I?
28. I’m a science museum located along the Charles River. Here you can catch laser light shows at the Mugar Omni Theater. What museum am I?
29. I’m a tasty variation on apple pie made with grated cheese and a crumb topping. I’m a fall favorite in Massachusetts. What am I?
30. I’m an elite private college located along the Charles River in Cambridge. My notable alumni include John Adams and John Quincy Adams. What college am I?
31. I’m a dessert consisting of vanilla ice cream sandwiched between two chocolate chip cookies. I was invented at a restaurant in Whitman. What am I?
32. I’m an amusement park located in the western part of the state. I feature the oldest operating roller coaster in the U.S. What park am I?
33. I’m a suburb of Boston where you can tour author Louisa May Alcott’s home, Orchard House. What town am I?
34. I’m a salty boiled dinner consisting of corned beef, cabbage, carrots and turnips. I’m especially popular in Boston on St. Patrick’s Day. What am I?
35. I’m an upscale town located along Cape Cod Bay. President John F. Kennedy had his summer White House here. What town am I?
36. I’m a city north of Boston where you can find America’s first public beach. I’m also home to the first chocolate factory in America. What city am I?
37. I’m an art museum located in Boston that houses works by Monet, Rembrandt, and the famous Copley portraits. What museum am I?
38. I’m a tasty grilled sandwich consisting of browned marshmallow and chocolate sandwiched between graham crackers. I was invented in Boston. What am I?
39. I’m a prestigious private university located along the Charles River in Cambridge. Notable alumni include Matt Damon and Ben Affleck. What university am I?
40. I’m a city along the Connecticut River known as the Baseball Capital of New England. I’m home to the Basketball Hall of Fame. What city am I?
41. I’m a tasty variation on clam chowder that substitute tomatoes for cream. I’m popular in summer in Massachusetts. What am I?
42. I’m a private research university located in Cambridge. My notable alumni include John F. Kennedy and Franklin D. Roosevelt. What university am I?
43. I’m a summer music festival hosted annually at Tanglewood in the Berkshires. The Boston Symphony Orchestra plays here. What festival am I?
44. I’m a popular baked good consisting of hot dogs wrapped in crescent roll dough. I originated right here in Massachusetts. What am I?
45. I’m a tasty version of apple cider flavored with cinnamon and cloves that’s popular in fall. What seasonal drink am I?
46. I’m a brewery founded in Boston that produces popular beers like Sam Adams. What brewery am I?
47. I’m an elite boarding school located in the Berkshires. Edith Wharton was my first female student. What institution am I?
48. I’m a tasty dish that consists of clams, potatoes, onions and linguica sausage all cooked together. I’m popular in southern Massachusetts. What dish am I?
49. I’m a posh beach community located on the North Shore. I’m home to the House of the Seven Gables. What town am I?
50. I’m a delicious dessert consisting of yellow cake with chocolate frosting between the cake layers. I’m popular in Boston. What am I?
51. I’m an architectural style popular in Massachusetts churches and buildings. My signature elements include white columns and symmetrical facades. What style am I?
52. I’m a tasty steamed sandwich consisting of corned beef, sauerkraut, Russian dressing, and Swiss cheese grilled between two slices of rye bread. What am I?
53. I’m one of the oldest operating theme parks in America. I feature a popular wooden roller coaster called The Cyclone. Where am I?
54. I’m a town south of Boston that hosted the legendary Tea Party protest in 1773. What town am I?
55. I’m an elite liberal arts college for women located in the Pioneer Valley. Notable alumnae include Emily Dickinson and Madeleine Albright. What college am I?
The Answers
1. I’m Massachusetts Bay.
2. I’m Harvard University.
3. I’m the Bunker Hill Monument.
4. I’m Phillips Academy Andover.
5. I’m New England clam chowder.
6. I’m Beacon Hill.
7. I’m the sinking of the RMS Titanic.
8. I’m the New England Patriots.
9. I’m the Boston Public Garden’s Make Way for Ducklings statues.
10. I’m Williams College.
11. I’m Henry David Thoreau.
12. I’m Tanglewood.
13. I’m Boston baked beans.
14. I’m Provincetown.
15. I’m the Oreo cookie.
16. I’m Faneuil Hall Marketplace.
17. I’m Boston Common.
18. I’m Lowell.
19. I’m College of the Holy Cross.
20. I’m Martha’s Vineyard.
21. I’m Williams College.
22. I’m the New England Patriots.
23. I’m Cape Ann.
24. I’m Plymouth.
25. I’m Filene’s Department Store.
26. I’m Sandwich.
27. I’m codfish cakes.
28. I’m the Museum of Science.
29. I’m apple crisp.
30. I’m Harvard University.
31. I’m the ice cream sandwich.
32. I’m Six Flags New England.
33. I’m Concord.
34. I’m corned beef and cabbage.
35. I’m Hyannis Port.
36. I’m Salem.
37. I’m the Museum of Fine Arts.
38. I’m the s’more.
39. I’m Harvard University.
40. I’m Springfield.
41. I’m Manhattan clam chowder.
42. I’m Harvard University.
43. I’m Tanglewood Music Festival.
44. I’m pigs in a blanket.
45. I’m mulled cider.
46. I’m the Boston Beer Company.
47. I’m The Mount.
48. I’m chouriço and peppers.
49. I’m Salem.
50. I’m Boston cream pie.
51. I’m Colonial/Georgian architecture.
52. I’m a Reuben sandwich.
53. I’m Six Flags New England.
54. I’m Boston.
55. I’m Mount Holyoke College.
Conclusion
How did you do with these riddles? Massachusetts has such a rich history and culture to draw from. Even lifelong residents of the state are sure to learn some new facts and tidbits of information from these brain teasers. The wide variety of clues, ranging from geography to sports teams, history, food, and more, reflect the diversity of attractions and activities that Massachusetts has to offer. Whether you aced this quiz or learned something new, exploring a state through its riddles is a fun way to engage with place. The next time you visit or talk about Massachusetts, you’re sure to impress friends with these intriguing riddles and their answers about the Bay State.
