55 Back From Winter Break Writing Prompts

Winter break is over, and students are back in the classroom, ready to jump into a new semester. But after weeks of holiday festivities, cosy days, and (let’s face it) lots of relaxation, getting back into the rhythm of writing can feel a bit challenging. That’s where these 55 engaging back-from-winter-break writing prompts come in!

Whether you’re looking to help your students reflect on their winter break experiences, spark their imaginations, or simply shake off the post-holiday blues, these prompts are perfect for getting pens moving and ideas flowing. From heartfelt reflections to whimsical storytelling, there’s something here for every writer.

Start the new year on a positive and productive note with these fun and thought-provoking prompts—perfect for journals, classroom discussions, or individual assignments.

55 Back From Winter Break Writing Prompts

Here are 55 engaging and creative writing prompts to help students reflect on their winter break, spark their imaginations, and jump-start their writing as they return to the classroom.

1. What was your favourite memory from winter break? Describe it in detail.
2. Write about a family tradition you celebrated over the break. How does it make you feel?
3. If you could relive one day from winter break, which day and why?
4. What is something new you tried over the break? How did it go?
5. Describe the most surprising thing that happened to you during winter break.
6. What was the best food you ate over winter break? Describe it using your five senses.
7. Write about your perfect snow day. What activities would you include?
8. If you could swap winter break with summer break, would you do it? Why or why not?
9. What did you miss most about school while you were on winter break?
10. Write about the funniest or strangest thing that happened to you over the break.
11. What is one thing you learned or discovered about yourself during winter break?
12. Describe a moment during winter break when you felt really happy. What made it special?
13. If you could share one thing from your winter break with the class, what would it be and why?
14. What was your favourite book, movie, or show you enjoyed over the break? What made it memorable?
15. Write about a time you helped someone during winter break. How did it make you feel?
16. Think of a moment when you were bored during winter break. What did you do to make it more interesting?
17. What kind of weather did you experience during winter break? How did it affect your activities?
18. Write about a new friendship or connection you made during winter break.
19. What’s one thing you wanted to do over the break but didn’t get the chance to?
20. How would you summarise your winter break in just three words? Explain why you chose them.
21. If you could turn one funny moment from winter break into a cartoon, what would it be about?
22. Write about the weirdest dream you had during winter break. What do you think it means?
23. If you had a camera, what one picture would you have taken over winter break to remember it forever?
24. Imagine your pet (or a made-up animal) writing about their winter break. What would they say?
25. What was the most unexpected thing that happened to you over the break?
26. Write about a time you laughed so hard during winter break that you couldn’t stop.
27. If you could create a “Winter Break Awards Show,” what would win the award for Best Day?
28. What was the silliest mistake or accident you made during winter break? How did you handle it?
29. If you could make a “Winter Break Survival Kit,” what three items would you include and why?
30. Write about something funny that happened while spending time with your family or friends over the break.
31. What was the most peaceful or relaxing moment of your winter break? Describe it in detail.
32. Write about a goal you had for winter break. Did you achieve it? Why or why not?
33. What was the best gift (tangible or intangible) you received over winter break?
34. Reflect on a moment when you felt grateful during the break. What made you feel that way?
35. Did you visit any new places over winter break? If so, what did you think of them?
36. Write about the people you spent the most time with during winter break. How did they make your break special?
37. What was one thing that made this winter break different from previous ones?
38. Did you experience any challenges or problems during the break? How did you overcome them?
39. Write about a winter break activity or tradition that you look forward to every year.
40. What is one thing you learned about someone else during winter break?
41. If winter break had a theme song, what would it be? Why did you choose it?
42. What’s the funniest or most awkward thing someone said to you during winter break?
43. Imagine writing a review of your winter break like it’s a movie. What rating would you give it and why?
44. If you could invent a new holiday based on something you did during winter break, what would it celebrate?
45. What was your most “oops” moment during winter break? Did you laugh about it later?
46. If your winter break was a comic book, what would the title and first panel look like?
47. Describe a moment when something unexpected made you smile during winter break.
48. If you could turn your winter break into a board game, what would the rules and objectives be?
49. What’s the most ridiculous or silly outfit you wore during winter break? Did anyone comment on it?
50. If your winter break had a mascot, what would it be, and why does it represent your break so well?
51. If you could create a holiday snack based on your winter break, what would it be called and what would it taste like?
52. What’s the most unusual or random object you came across during winter break, and what’s the story behind it?
53. Imagine your winter break was turned into a reality TV show. What would the most dramatic or funniest episode be about?
54. If you could turn one moment from winter break into a hilarious meme, what would it say or look like?
55. Write about a time you tried something new over winter break and how it turned out—did it go as planned or take a funny twist?

For more ideas see these resources:

• 62 New Year’s Writing Prompts For 2025
• 50+ New Year Journal Prompts
• 31 January Writing Prompts + Free Printable

Summary

Writing after winter break is the perfect way to help students ease back into their creative flow, reflect on their experiences, and set the stage for a successful semester. These 55 prompts offer a mix of personal reflections, imaginative fun, and thoughtful goal-setting to keep students engaged and excited to write. Whether you’re a teacher looking to spark meaningful classroom discussions or a parent encouraging writing at home, these prompts are a great way to start the new year with creativity and purpose.

What are your favourite ways to get students writing after winter break? Share your thoughts in the comments below.