75+ Workplace Fall & Halloween Icebreaker Questions

Why seasonal icebreakers work their magic 🍂🎃

Icebreakers are kind of like warm apple cider: they make people feel cozy, welcome, and ready to open up. Whether you’re starting a team meeting, hosting a virtual event, or planning a seasonal celebration, the right question can spark genuine connection.

And here’s where things get extra fun: tying your icebreakers to the season. Asking about fall flavors or Halloween costumes taps into experiences most people share. Suddenly, your coworkers are laughing over pumpkin spice debates or swapping trick-or-treat memories. It’s a low-pressure way to bond over something lighthearted, while still building the trust and camaraderie that fuels great teamwork.

Ready to kick things off? Grab a pumpkin spice latte, throw on your coziest sweater, and dive into this ultimate list of fall- and Halloween-themed icebreaker questions.

🍂 Fall Icebreaker Questions

Fall Food & Drinks

1. Pumpkin spice latte: love it or leave it?
2. What’s your go-to fall beverage—cider, cocoa, or something else?
3. Apple pie or pumpkin pie?
4. What’s your favorite fall soup or comfort food?
5. Do you like savory or sweet pumpkin dishes better?
6. If you had to eat only one fall food for a week, what would it be?
7. What’s your favorite Thanksgiving side dish?
8. Homemade or store-bought apple cider donuts?
   
   1. Learn how to make your own donuts in our Donut Making Class
9. Candy corn: yay or no way?
10. Which fall flavor deserves more hype: maple, cranberry, or pecan?

Fall Activities & Traditions

11. What’s your favorite fall activity?
12. Pumpkin carving or pumpkin painting?
    
    1. Share the fun of Pumpkin Painting with your team
13. Apple picking or corn maze?
14. Do you go to fall festivals?
15. Favorite outdoor fall sport or game?
16. Do you decorate for fall in September, or wait until Halloween/Thanksgiving?
17. Hayride or haunted house?
18. What’s the most “fall” photo you’ve ever taken?
19. Did you ever rake leaves just to jump in them?
20. What’s your favorite fall memory?

Fall Vibes & Scenery

21. What’s your favorite fall color?
22. Early fall (warm days, cool nights) or late fall (crisp and chilly)?
23. What’s your favorite fall smell?
    
    1. Want to make your own candle for the season? Check out our Candle Making Class
24. Mountains, forests, or city streets—which looks best in fall?
25. What song feels like fall to you?
26. Rainy fall days or sunny fall days?
27. What’s your ideal fall weekend?
28. Do you take fall photos or just enjoy the view?
29. What’s your favorite fall holiday?
30. Cozy nights in or outdoor adventures?

🎃 Halloween Icebreaker Questions

Costumes

31. What was your favorite Halloween costume as a kid?
32. Do you prefer funny or scary costumes?
33. What’s the best group costume you’ve ever seen?
34. Have you ever made your own costume?
35. What’s a costume you’ve always wanted to try?
    
    1. Want some ideas? Play Halloween Guess Who
36. Do you dress up your pets for Halloween?
37. If you could dress as any fictional character this year, who would it be?
38. Couple’s costumes: cute or cringe?
39. What’s your most last-minute costume idea?
40. Classic costumes (witch, vampire) or niche costumes?

Candy & Treats

41. What’s the best Halloween candy?
42. What’s the worst Halloween candy?
43. Did you ever trade candy after trick-or-treating?
44. Chocolate or fruity candies—what’s your pick?
    
    1. Fan of chocolate? Try our Halloween Mystery Chocolate Tasting experience
45. Do you like to hand out candy on Halloween?
46. If you could invent a new Halloween candy, what would it be?
47. Did you ever get something unusual in your trick-or-treat bag?
48. What candy did you always eat first?
49. Do you still buy Halloween candy for yourself?
50. What’s the most overrated Halloween candy?

Scary vs. Cute Halloween

51. Do you like scary movies or avoid them?
52. Haunted houses: yes or no?
53. Spooky or cute Halloween décor?
54. What’s your favorite Halloween movie?
55. Ghosts, zombies, or vampires?
56. Do you like telling scary stories?
    
    1. Grab some other coworkers who do for Scary Ghost Stories
57. Do you carve creepy faces or cute designs into pumpkins?
58. What’s the scariest thing that ever happened to you on Halloween?
59. Trick-or-treaters: scary costumes or silly ones?
60. Would you rather star in a horror movie or a Halloween comedy?

Halloween Memories & Traditions

61. Did you trick-or-treat as a kid?
62. Do you still dress up as an adult?
63. Did your family have any unique Halloween traditions?
64. What’s your earliest Halloween memory?
65. Did you ever win a costume contest?
66. Do you decorate your house for Halloween?
67. Did you ever get spooked while trick-or-treating?
68. Do you enjoy Halloween parades or events?
69. What’s the best Halloween party you’ve been to?
    
    1. Want to plan a Halloween party you coworkers will remember? Check out all our Halloween experiences!
70. What are your thoughts on trunk or treating?

Just for Fun

71. If you could be any iconic Halloween monster for a day, who would you pick?
72. Which Halloween emoji is your favorite? 🎃👻🕷️🧛
73. Would you rather live in a haunted house or a pumpkin patch for a week?
74. Do you believe in ghosts?
75. What’s your favorite Halloween pun?
76. If Halloween had a mascot other than a pumpkin, what would it be?
77. Would you rather get 100 pieces of candy or constant praise for YEARS for one amazing costume?
78. If you could rename Halloween, what would you call it?
79. How good would you do in Halloween Trivia?
    
    1. Put your skills to the test in our Halloween Speed Trivia
80. What’s the weirdest Halloween decoration you’ve ever seen?

Want to try a guided round of icebreakers? Gather your team at Confetti's Water Cooler for a getting-to-know-you team building activity!

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Final Treats (No Tricks) 🎃

Seasonal icebreakers are a simple, festive way to bring people together—whether your team is scattered across time zones or gathered around the same conference table. Talking about favorite pies, nostalgic costumes, or spooky traditions helps teammates see each other as more than job titles.

And when people feel connected, collaboration and culture thrive. So the next time you’re planning a fall meeting, a team-building session, or just a Monday morning kickoff, sprinkle in a few of these questions. Who knows—you might uncover your team’s hidden apple-picking pros, pumpkin-carving artists, or candy connoisseurs.

After all, building culture doesn’t have to be scary 👻 See all of Confetti's scary good fall and Halloween experiences here.