Me-Made-May
📅 May 1–31
A wardrobe challenge, not a making contest: set your own pledge to wear your handmade clothes more (or differently) during May. Open to anyone with…
#MeMadeMay26
May 2027 Art Challenges
4 challenges start or run in May 2027. Prompt lists usually drop a few weeks before; we link them as soon as they are out.
MerMay
📅 May 1–31
Draw mermaids all May. Started in 2016 by former Disney animator Tom Bancroft; the official prompt list is posted around April
#mermay
National Scrapbooking Day
📅 Early May (Sat May 2 in 2026)
Scrapbookers' annual celebration; shops and designers run layout challenges, games and sales over the
The 100 Day Project
📅 100 days; 2026 round started February 22
Pick one creative action and repeat it every day for 100 days. Free; the official start date is announced each year in the project
#The100DayProject
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.