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: 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.
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.