50 Spectacular Boston Trivia Questions and Answers

Dive into our Boston Trivia! From its iconic colonial landmarks to contemporary cultural shifts, Boston is a city brimming with tales waiting to be told. How well do you know the Cradle of Liberty? Whether you’re a seasoned Bostonian, a curious traveler, or just someone with a thirst for knowledge, this Boston trivia collection promises to unveil fascinating snippets of Boston’s storied past and vibrant present. Test your knowledge or challenge a friend with these engaging Boston trivia questions. Let’s explore the heart of New England, one trivia at a time!

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Boston Trivia

1. What year was Boston founded?

2. Which famous event in 1773 protested British taxes?

3. Which historic American trail starts in Boston?

4. Boston is home to the oldest public park in the U.S. What is its name?

5. What is the name of the oldest institution of higher education in Boston?

6. Which Boston infrastructure is commonly referred to as ‘The Big Dig’?

7. In which neighborhood can you find Boston’s Italian community?

8. Which historic ship can be visited at the Charlestown Navy Yard?

9. Which annual Boston event takes place on Patriots’ Day?

10. Which American patriot and silversmith is famous for his ‘midnight ride’?

11. Which body of water borders Boston to the east?

12. What Boston building is known for its golden dome?

13. Boston has the oldest continuously operating subway system in the U.S. In which year did it open?

14. Which Major League Baseball team calls Boston its home?

15. At which Boston museum can you find a large glass flower collection?

16. What is the official state dessert of Massachusetts, commonly found in Boston?

17. What is the name of Boston’s main international airport?

18. What iconic Boston stadium was replaced by Fenway Park?

19. Which bridge connects Boston to the city of Cambridge?

20. Boston University’s bridge is unique as it’s the only place in the world where a boat can sail under what?

21. Which Boston library is the third largest public library in the U.S.?

22. What is the name of the island group in Boston Harbor?

23. What is the name of the 62-story skyscraper in Boston’s Back Bay?

24. Which Boston square is known for its historic market?

25. Which revolutionary war battle is commemorated by a monument in Charlestown?

26. What popular Boston street has been referred to as the ‘Rodeo Drive of the East’?

27. Which Boston arena is home to the Celtics and the Bruins?

28. Which famous composer and conductor led the Boston Symphony Orchestra for many years?

29. What historic Boston site was a gathering place for colonists demanding independence?

30. Which famous Boston-born president has a presidential library in the city?

31. Which colonial-era meeting house in Boston was the site of many revolutionary gatherings?

32. What Boston museum is renowned for its collection of American art?

33. Which Boston cemetery is the final resting place for Paul Revere, Samuel Adams, and John Hancock?

34. Which Boston school, founded in 1635, claims to be the oldest public school in the U.S.?

35. In Boston’s North End, what narrow street is known to be one of the city’s oldest?

36. Boston was the birthplace of a famous American poet who wrote ‘The Raven’. Who was he?

37. Which Boston church, completed in 1877, is known for its beautiful stained glass windows?

38. In which Boston neighborhood can one find Symphony Hall?

39. What type of clam dish is a popular delicacy in Boston?

40. What historic Boston hotel, opened in 1855, has hosted numerous U.S. presidents?

41. What public transportation system serves Boston and its suburbs?

42. Which Boston waterfront area underwent significant revitalization in the 20th century?

43. Which U.S. founding father was born in Boston on January 17, 1706?

44. Which Boston institution, founded in 1820, claims to be the oldest restaurant in continuous service in the U.S.?

45. What beloved Boston sports broadcaster is known for his famous phrase, ‘And this ballgame is over!’?

46. Which American Revolution figure, known for her poem ‘To His Excellency, George Washington’, was from Boston?

47. Which festival, celebrating Boston’s seafaring history, attracts hundreds of thousands of visitors each summer?

48. Boston’s South End is known for its collection of what type of architectural style homes?

49. Which Boston park, designed by Frederick Law Olmsted, features a pond and a zoo?

50. Which annual event celebrates the lighting of Boston’s official Christmas tree?