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 prompt is “Dark Fairytale”
Now, I cannot draw. But my sister, Emily Pillard, can. She and I have collaborated for the past three years to create stories accompanied by beautiful illustrations. We’re at it again for the fourth year in a row with a brand new story and stunning artwork.
Read on to discover the whole story! And don’t miss out on our 2024 story “Monster Mash,” our 2023 story “Haunted House,” and a series of micro-stories for the 2022 theme, “Season of the Witch!”
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Drawtober 2023: Moonlit Conservatory
I pause on the threshold. Moonlight fills the room through the huge glass windows, edging the plants in silver. A fountain, water trickling out of the mouth of a stone sea serpent, sits in one corner of the room, ringed with wrought-iron furniture that glows black in the dim light. The air in here is thick with moisture and heavy with floral scents. There is only one other door from this room, leading out into the cemetery, and it is padlocked. The Keeper has the only key.
Drawtober 2023: Devious Dining
Everyone has different notions of what the dead eat. Fruits and breads, sugar skulls, the souls of the living. Fairy folk are just as enigmatic, with dishes of milk and honey favored as offerings, though many of the fae creatures I’ve met prefer flesh to any dish of warm milk.
Under different circumstances, I would be more precise in my culinary efforts. But All Hallows Eve is coming up, and I don’t know what I’m dealing with. I don’t want this thing—whatever it is—wandering the House any longer than it already has.
Drawtober 2023: Moth-Bitten library
The library stands behind an unassuming oak door in far-flung corner of the House. The brass knob is shiny and smooth from years of use—the room is a favorite among the House’s residents. Jack, the Keeper before me, tried at one point to install a television set, but something about the House’s location meant that it never worked. As a result, our primary forms of entertainment here continue to be dances and books. Books are generally easier to come by.
Drawtober 2023: Overgrown Cemetery
I’ve always quite liked the House’s cemetery. It doesn’t even seem strange to me anymore that the House has one. Of course it does. It sits on the crossroads after all. A cemetery is probably a requirement.
Drawtober 2022: The Corvid Ball
It’s late in the evening
When I hear a tapping,
A murmurous sound in my room.
The flutter and mutter
Of one of the murder
Of crows that circle the moon.
He sits at my window,
Inviting me onward
With just a slight tilt of his head
As if to say, “No one
Will know if you wander
While everyone else is abed.”
Drawtober 2022: The Bargain
In her finest black gown, Branwen stood and surveyed the place where The Game would be played. The flat stone sat at the peak of the hill that rose out of the bog, its edges worn soft by time. Two large mushrooms (grown by herself, thank-you-very-much) faced each other on opposite sides of the stone, ready seats for tonight’s encounter. Around the hillock Branwen had lit an army of candles, their flames giving a flickering, unsettling light to the darkness of the bog.
Drawtober 2022: Grimalkin
I was staring up, waiting for my Lady’s eye to become visible, when a shadow peeked over the rim of my prison. I blinked, wondering if I was seeing things, but when my eyes opened, the shadow remained, resolving itself into a head with a pair of pointed ears. A pair of eyes, green as glittering emeralds, stared down at me from high above.
Why languish you there, moon sister?