Hello! I have decided to embark on a mid-month 21 day writing challenge.
October is my favorite month, so in the spirit of “trying to live in the present,” I have compiled a list of writing prompts inspired by Fall, the month of October, and self-development. Parameters for the challenge include:
Must be at least 400 words.
Must follow the prompt of the day in some way.
October 2025: 21 Day Writing Challenge Prompt List
Autumn... What do you notice? What does autumn mean to you? Do you like it? Why?
Harvest... The harvest is traditionally a time when people gather the crops they planted earlier that year. The harvest symbolizes abundance, gratitude, and community. Write about the harvest.
Favorite Fall Memory... Reflect on your favorite fall memory. What details stand out the most?
I Am Looking At... “I am looking at…” Whenever you get stuck, write “I am looking at” again and keep going. Be specific — not a car, but a Ford Mondeo. Not a tree, but a sycamore.
I’m Thinking Of... I’m thinking of… What has been on your mind recently?
I Remember... The simplest thing to do is to use “I remember” as your sentence starter. You might find yourself writing “I remember…” and then running into an extended story, a rant, or something else entirely. Here are a couple of more specific ideas: a picture of a teacher you had in elementary school; a time when you were in trouble in class; how you first learned to read.
Mask... What mask are you wearing? Why are you wearing it? What’s underneath it?
All The ___ Of My Life… This idea comes from Families Writing by Peter Stillman. Stillman wrote a list of all the cars in his life — naming them and adding a defining comment. (A ’38 Packard sedan whose clutch my girlfriend blew out. A ’48 Buick convertible that honest-to-God liked me. A ’35 Dodge thronging with old ladies’ ghosts. A ’65 Ford Galaxy in which I destroyed a Karmann Ghia, a privet hedge, and finally my relative innocence. A ’72 Audi so corrupt I still can’t bear talking about it. An ’82 Rabbit that helped me discover where my sciatic nerve is.)
Back to School… Teach me something. It doesn’t have to be a traditional subject. How about how to tie a shoe, be a good mother (or father), clean out the refrigerator, make a pudding, or change a tire? Something that is deep in your bones — like driving in rush hour to work each day.
Haunted House... What is your home like? Where you live now. Take a tour around the house. Show us around. Will you be estate agent, historian, gossip, or family archivist? What are the tourist attractions? The most frequented places? Show us a hidden treasure. List its seven wonders. Go.
Recipes... Think of a recipe you love. It could be as simple as your lazy comfort meal. How did you discover it? What kind of dinnerware do you serve it in? Have you discovered a new recipe recently?
Silence of the Lambs... Write about quiet. What can you hear? What is absent? Have there been times when all you wanted was quiet? Or when it was too quiet — often ominous. Write about quiet.
Pumpkins... That’s your prompt. Write about pumpkins. Anything about them: How they look (inside or out), going to buy one at the grocery store, scooping out and cooking their seeds, etc.
Ghost Stories... We all tell stories. We tell stories to make sense of our days and our lives. We have stories that are our touchstones — ones that define us, guide us, or just annoy our relatives. Write one of the stories you tell over and over again.
Seeds... What “seeds” have you planted earlier this year that are finally showing results?
Five Minute Autobiography... This is an interesting idea that can become compulsive. Set a timer and write your whole life in five minutes. When the time is up, stop. You can have another go — start from where you left off, or begin again from the beginning. The idea is to get the whole life down in five minutes, and then experiment with strategies that allow you to do that.
Sleepy Hollow… Where I have slept. List the places where you have slept. Which one will you write more about?
Halloween... What is your favorite Halloween memory? What does Halloween mean to you? Do you wonder about the history of Halloween at all? Just write about Halloween. Happy Spooky Day!
First Meetings... Write about all the first meetings you’ve ever had — with a lover, a caretaker, a teacher, a friend, a lawyer, the owner of a shop, or a hairdresser.
Goals... What were your annual goals this year? How close are you to achieving them? How can you wrap them up before the end of the year, or pivot to an achievable goal you can reach in time?
Looking Forward... What are you looking forward to the most at the end of the year?
Happy Writing! Please tag me if you’d like to join me on this Writing Challenge. 🎃
Thank you to the National Writing Project UK for inspiration in compiling this list.