Promptober 2026
Thank you for drawing with us! For 31 spooky days, artists of every age and skill level drew the daily prompt and filled our feeds and the Draw or Die Discord with bats, ghouls, and jack-o’-lanterns. Year five is in the books, and we couldn’t have done it without you or our amazing sponsors.
- 31 spooky prompts
- 13 prize packs
- $1,800+ in prizes
Year five: 31 days, 31 prompts
Promptober is the Draw or Die Club’s free October drawing challenge. Every day brought a new spooky prompt, and you drew it in whatever medium you love.
- Draw the day’s prompt from the 2026 calendar.
- Post it on social or in the Draw or Die Discord with #Promptober.
- Earn one prize entry for every drawing, up to 31.
- Win by placing entries on 13 sponsor-stuffed prize packs, drawn live on YouTube on Nov 7.
Our amazing sponsors
Promptober is free to enter because these brands stuffed our prize packs with over $1,800 in goodies. Show them some love and give them a visit.
Blackwing
The pencils artists and writers swear by. Gift cards in the loot.
Visit Blackwing →Makers Cabinet
Beautifully engineered drawing tools, from the Ferrule pencil extender to the Høvel pencil plane.
Visit Makers Cabinet →Rickshaw Bagworks
San Francisco-made pen cases, including our custom Draw or Die Fillmore.
Visit Rickshaw Bagworks →Field Notes
Pocket notebooks that made it into every single prize pack.
Visit Field Notes →SketchBox
Monthly boxes of premium art supplies, plus their Signature markers, inks and watercolors.
Visit SketchBox →Art Toolkit
Pocket-size watercolor palettes and field kits for sketching anywhere.
Visit Art Toolkit →Dango Products
Rugged everyday-carry gear, like the P02 Pioneer travel wallet.
Visit Dango Products →See you next October!
Promptober returns in October 2027 with new prompts, new prizes and the same spooky fun. Join the email list below to be the first to know when the 2027 calendar drops.
Can’t wait? Draw with us all year
Join the Draw or Die Club
Promptober only lasts a month, but the club draws all year. Get a fresh prompt every day and keep the habit you built in October.
This month: Skully’s Imagination Workshop. Roll the dice, create a character, and take them on a month-long adventure all the way to the final boss battle.
All ages, no skill required. Cancel anytime.
Drawing Playlist
Spooky tunes to sketch to, curated by the club.
Come Hang with Us
Share your work, get feedback, and find your fellow night owls (er, bats) in the Draw or Die Discord, or get club news by email.
Join Our Discord