Every year on Instagram, artists of all kinds participate in #Drawtober, an art challenge consisting of six prompts spread out over the month of October. This year, the Drawtober crew has rounded up their top prompts from the last ten years for one last hurrah.

Now, I cannot draw. But my sister, Emily Pillard, can. She and I have collaborated for the past four years to create stories accompanied by beautiful illustrations. We’re at it again for the fifth year in a row with a brand new story and stunning artwork.

Read on to discover the whole story! And don’t miss out our 2025 story “Dark Fairytale,” 2024 story “Monster Mash,” our 2023 story “Haunted House,” and a series of micro-stories for the 2022 theme, “Season of the Witch!”

J. C. Pillard J. C. Pillard

Drawtober 2026: Pumpkin Head

Imagine, if you will, a meadow cradled in the soft hands of a valley. Rolling hills surround the valley, farmland eventually giving way to forest.

Imagine a tree at the center of this meadow, decked in hanging lights and the last vestiges of red leaves. Imagine tables set around the tree, laden with pies and candies, ruby red apples and the last of the season’s peaches. The air smells of spices and burning leaves and the faintest hint of snow.

Then, of course, imagine the people.

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J. C. Pillard J. C. Pillard

Drawtober 2026: Fungus Collector

Up until his arrival, Barley had been having a lovely day. She’d woken up to the bite of frost on the air and scurried outside as fast as she could with a basket in paw, eager to begin her foraging. Like many of her kind, Barley was an industrious sort of squirrel. Before even the first hint of winter had hit the breeze, she had begun stockpiling for a long winter. Today, she planned to find mushrooms.

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J. C. Pillard J. C. Pillard

Drawtober 2026: Stitched Together

Snip. Snip. Snip.

The little gold scissors in Amelia’s hands were so even, so regular in their work, that they sounded like a clock telling time. Errant strings and loose ends fell away beneath them.

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J. C. Pillard J. C. Pillard

Drawtober 2026: Wicked Apothecary

The shop sat in a little alley off the town square. An unassuming door set into the brick wall of a larger building, its wood worn and brass knocker tarnished. A pair of windows bracketed the door, though you’d be hard pressed to see through them—the plants that grew in the windowsills were so dense they blocked any view into the store. A much-battered sign hung above the door on iron brackets.

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J. C. Pillard J. C. Pillard

Drawtober 2026: Shadow Prince

In the darkness lingering at the edges of Halloween’s dawn, Prince crept along the road like a shadow. He had a satchel slung across his back filled with invitations to tonight’s party. Most of the invitations had gone out weeks ago, but a few had been returned undelivered. It was now his duty to deliver them.

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J. C. Pillard J. C. Pillard

Drawtober 2026: Witch’s Garden

Pumpkins were particularly hard for her. Oh, they always looked fine—rotund and perfectly colored. That wasn’t the problem. The problem was what you found inside the gourd, for Nellie’s pumpkins often grew with strange innards—hungry mosses or strange spiders or sometimes simply rotten. In the years that she had been growing pumpkins in the garden, she had never managed to grow a normal one.

None of that would do for tonight. She needed a good pumpkin, the perfect pumpkin, in fact, to carve for the Master of Revels.

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J. C. Pillard J. C. Pillard

Drawtober 2025: Enchanted Masquerade

The Queen’s palace rises out of the landscape suddenly, a mountain you somehow hadn’t noticed before. I heard once that the structure was grown, not built, and I would believe it. Towers swirl around each other like tree limbs, and the domes seem made of frost and ice. Faerie fire illuminated the inside as we approached, making the place glow like an ember. The music—for there is always music here—was audible even from far down the hill. Lilting tunes of pipes and drums and strings that begged one to dance.

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J. C. Pillard J. C. Pillard

Drawtober 2025: Troll Toll

While I was writing you, the earth began to shake. It trembled so violently that it was everything I could do to keep my bag and myself from tumbling to the ground. The ground where I stood twisted nearly ninety degrees, leaving me to scramble upwards towards a place that had just recently been lower than where I was sitting. Meanwhile, the neighboring hill shifted upwards, growing even larger. A craggy face appeared—long, wide nose, yellow eyes, and strings of lank hair I had taken to be algae. Those yellow eyes blinked, and an enormous hand raised up to rub sleep from them before they looked upon me where I stood upon the thing’s leg.

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J. C. Pillard J. C. Pillard

Drawtober 2025: Spellbound Princess

The road to Glaustone Grove is a winding one. We’ve been walking it for four days, and my feet grow more tired every day. The atmosphere is becoming more oppressive the farther we go—the sky grows darker, the wind blows more coldly. Leafless branches twist against the sky, with only a few orange and yellow leaves clinging against the growing chill.

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J. C. Pillard J. C. Pillard

Drawtober 2025: Mushroom Fairy

Rook didn’t fly off as I was hoping. Nor has he flown off in the past five days that we’ve been traveling. Instead, he has followed me like a persistent leech. He even seems to have formed an unholy alliance with Blue, because they are both convinced that what I need at this moment is not to find the door to the Queen’s Court, but instead to find a dress to wear to the damned Masquerade.

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J. C. Pillard J. C. Pillard

Drawtober 2025: Toad Astrologer

Of the many ways into Faerieland, the closest to Hulspeth is the road that leads through Dogmore. The little town we knew is no longer a mere byway. It has grown quite a bit, and in the growing it has become more disreputable as well. When I first stepped into town, feeling the world shimmer around me as I entered the Other Country, I found myself taken aback. The main road has been widened to accommodate larger crowds. Little carts lined the street, selling dreams and potions and charms of every variety.

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J. C. Pillard J. C. Pillard

Drawtober 2025: Candlelit Messenger

I had expected something grander, to be honest. An owl or a nightingale bedecked in moss and starlight. What I found instead was only a bluebird. Her dusty blue and orange feathers were puffed up with fury, and she wore a little lantern atop her head, the candle inside somehow still lit. Tied to her leg was, of course, the message I was after.

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J. C. Pillard J. C. Pillard

Drawtober 2024: Monster

It is always awkward when one is caught with one’s hand in the proverbial cookie jar. And Ella, her face and neck and chest coated with red, was elbow-deep in a cookie jar of an entirely different kind. The King was very thoroughly dead (most of his vital organs having disappeared down Ella’s throat), and Lucinda was standing in the doorway with an expression of shock on her face. In that moment, the fog of hunger lifted from Ella’s thoughts. Instead, she found herself deeply, deeply ashamed.

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J. C. Pillard J. C. Pillard

Drawtober 2024: Ghost

It was a crypt. Elaborate stone coffins with carved lids lined the chamber. Those silent tombs depicted men and women in repose, holding lilies, swords, cups, books, and bones. Some wore crowns; others did not. Some were cracked and near blackened with age, while others looked well-kept indeed. Turning around, Ella started back. She had been leaning against the newest of the bunch—the stone was still bright, the woman carved into its lid fresh and unbroken. This was not the reason she started back.

No, that was because of the ghost.

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J. C. Pillard J. C. Pillard

Drawtober 2024: Undead

The castle on the hill shone with light.

Oh, it still brooded, dear reader. But it did so with flare now—glimmering torches lined the outer walls, and vibrant fires crowned the many towers of the King’s menacing palace. As Ella’s pumpkin coach pulled up to the front entrance where the drawbridge still lay down, she couldn’t help but stare up at the castle with a kind of cold fear. That same premonition that had so rattled her when her step-sister had left earlier in the evening shuddered through her bones again.

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J. C. Pillard J. C. Pillard

Drawtober 2024: Witch

Among the many strange creatures that inhabited the Kingdom, anyone who wielded magic was looked upon with great suspicion. You may find this strange, but think of it this way: if you know your neighbor is a vampire, then you know roughly what to expect. Garlic on the windowsills and doors will keep them at bay if they are feeling truly ravenous. Even werefolk can be kept out with a well-placed silver doorknob. But a neighbor with magic? Why, there’s ten-thousand ways they could kill you and not even realize it. Spells of flame, spells of snow, spells to unwind health and bestow old age. A sorcerer has so many ways to make your life hell, and there’s not one good folk remedy to stop it all.

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J. C. Pillard J. C. Pillard

Drawtober 2024: Shapeshifter

What happened was that Ella had to go grocery shopping.

While it is true that Ella’s step-family subsisted off the blood of mortals, there is nothing to say that such blood should not have a little seasoning to it (except garlic, of course). Being that they did not have much money, Ella used what little they did have to frequent a local grocer who was willing to barter with her.

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J. C. Pillard J. C. Pillard

Drawtober 2024: Vampire

Once upon a time, there was a rich man who loved his wife very much. Together, they had but one daughter, a beautiful, delicate child named Ella. When Ella was eight years old, her mother fell terribly ill. As her end drew near, Ella’s mother called for her only child to come near her bed. And when Ella approached, her ailing mother rose up and tried to tear the girl’s throat out.

Oh, I’m terribly sorry. Did you think you knew where this story was going? I suppose I rather misled you. Because while this is a Cinderella story, it is not that Cinderella story.

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J. C. Pillard J. C. Pillard

Drawtober 2023: Ghostly Ballroom

The stairs leading down onto the ballroom floor are ablaze with ghostly light when I arrive. Strains of orchestral music float up the staircase, a dark waltz that mixes with the sounds of laughter and the beating of wings. From where I stand on the stairs, I see imps flitting through the air, chasing pixies and witches on their brooms. On the dance floor, ghostly couples swirl together.

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J. C. Pillard J. C. Pillard

Drawtober 2023: Dolls in the Attic

The stairs come out of the ceiling with a dusty thud, and each step creaks as I ascend. Yellow sunlight, coming through a round window that hasn’t been cleaned in far too long, illuminates crates, boxes, old furniture, discarded knickknacks, and forgotten clothes. Dress forms with sheets draped over them like simulacra ghosts peek out of the shadows.

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