Folktember
📅 September
A September challenge of folklore-inspired prompts (e.g. 'Forest Sprite'), announced on Instagram each
#folktember #folktember2026
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September 2027 Art Challenges
3 challenges start or run in September 2027. Prompt lists usually drop a few weeks before; we link them as soon as they are out.
Hat'tember
📅 September 1–30
A month-long hat-making celebration with prize draws (two $50 gift certificates in its current edition). Hats must use Ancient Arts yarn to qualify…
#AAYhattember
Socktember
📅 September 1–30
A month of socks on the Winwick Mum blog with a knit-along on Ravelry: beginners use the free Basic 4ply Socks pattern, experienced knitters the new…
No challenges match that medium this month.
Also running every month
Doodlewash Monthly Art Challenge
📅 Every month
A new set of 30–31 optional daily prompts every month for watercolor, drawing, or both. Join anytime; hashtag uses the month
#doodlewashOctober2026 (changes monthly)
Draw This In Your Style (DTIYS)
📅 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
Hobby Streak
📅 Anytime
Miniature painters commit to at least 30 minutes of hobby work every day and post progress; miss a day and the streak
#HobbyStreak
r/SketchDaily
📅 Every day
A subreddit that posts a new drawing theme every day (plus an alternate theme), often tied to the month's big
Sketchbook Skool Draw with Me
📅 Weekly
A free weekly live hour of drawing together, part lesson, part draw-along, even if you haven't drawn in
No challenges match that medium this month.