Never miss a start date + free watercolor Christmas clip art ↓
October 1–31
A bird a day for October: 31 named bird species (2026 included the shoebill and resplendent quetzal), with day 31 as artist's
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October 2027 Art Challenges & Drawing Prompts
Looking for a October drawing challenge or daily art prompts? 12 challenges start or run in October 2027. Prompt lists usually drop a few weeks before; we link them as soon as they are out, and you can always start late.
Prizes this monthOctober 2027 challenges with prizesOrctober: prizes as stated by the organizer. Check their rules for details.See the details →
October 1–31
A botanical alternative to Inktober focused on poisonous plants and flowers. In 2026 each plant spans 2–3 days (castor bean, deadly nightshade,…
October 1–31
Mab Graves' spooky October drawing challenge with an official daily prompt list (full, weekly and 'lite' printable
#drawlloween
October 1–31
RetroSupply's 31-day Halloween drawing challenge (skulls, black cats, haunted houses...). The 2026 calendar reuses the original 2021 prompts; there…
October 1–31
The classic: make an ink drawing every day in October (or every other day, or weekly). Official 31-word prompt list is published each year; pencil…
#inktober #inktober2026
October 1–31 (prompts Mon–Sat, 27 in 2026)
Magma's free October challenge: a prompt and a live shared-canvas Art Jam every day Monday–Saturday. Bring the Inktober list or use theirs. Free…
#jamtober
October 1–31
A free, beginner-friendly painting challenge with one simple prompt a day (cow, taco, pumpkin pie...). Any paint works; a 10-minute painting counts.…
#justpaintOctober2026
October (list released September 1)
31 prompts inspired by horror, folklore, mythology and dark fiction, released every September 1, each with a 'track of the day'. No rules: draw daily…
#OfficialMonstober
October 1–31
Orcwood Games' month-long art event: 31 daily prompts (2026 ran from 'The first orc' to 'King of the pumpkins'), any medium (paint, sculpt, craft,…
October
A community challenge created in 2018 as an Inktober-style alternative: one artwork a day in October based on that year's prompt list, in any
October 1–31
31 days of illustration prompts from the SCBWI illustration community. Any medium; the goal is a daily practice, not perfection. Writers welcome
#scbwiArtober2026
October 1–31
A low-pressure October sock knit-along on Ravelry: a 31-stripe yarn (one stripe per day). Crochet welcome; you buy the KAL yarn to join (orders…
No challenges match that medium this month.
Also running every month
Every month
A new set of 30–31 optional daily prompts every month for watercolor, drawing, or both. Join anytime; hashtag uses the month
#doodlewashNovember2026 (changes monthly)
Anytime (each host sets a deadline)
An artist posts an original piece and invites everyone to redraw it in their own style, tagging the host. Hosts set the rules, deadline and sometimes…
#DTIYS #drawthisinyourstyle
Anytime
Miniature painters commit to at least 30 minutes of hobby work every day and post progress; miss a day and the streak
#HobbyStreak
Every day
A subreddit that posts a new drawing theme every day (plus an alternate theme), often tied to the month's big
Weekly, Thursdays 9 am PT / 12 pm ET (live on YouTube)
A free weekly live hour of drawing together on YouTube: Danny Gregory picks a topic and everyone draws along, part lesson, part pep talk, even if you…
#SBSDrawwithme
No challenges match that medium this month.
Card maker or Cricut crafter? 15 papercraft challenge blogs post new themes every week or month. See papercraft & card challenges →