61+ Best Art Challenges In 2022 - Art Side Of Life®

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70+ Fun Art Challenges You Must Try in 2025

By Iva Mikles • Artist and Illustrator •

Updated: 23 Sep 2025 • Artist Resources » Art Challenges

Below is a list of 70+ (!) art challenges, which are still being held as of 2025 and have great themes and communities behind them. Discover them below and challenge yourself! And most importantly, have fun ❤️

Quick jump

• Monthly Art Challenges
• Coloring Challenges
• Drawing and Sketching Challenges
• Character Design Challenges
• Photography Challenges
• Creativity and Inspiration Challenges
• Painting Challenges
• Artist Promo Challenges
• Most Popular Art Challenge
• Crafting Challenges
• TikTok Art Challenges

Monthly Art Challenges

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January Art Challenges

Art Journal January, Creatuanary, From A to Z, #100Heads

February Art Challenges

Figuary, Faerie February, February Faces

March Art Challenges

March Meet The Maker, Magical March, March of Robots

April Art Challenges

PleinAirpril, 100 Day Project, Wizardapril

May Art Challenges

Mermay, Munchy May

June Art Challenges

Kaijune, Junicorn, Childhood Week, Doodlewash

July Art Challenges

World Watercolor Month, Julycanthropy, Kaijuly

August Art Challenges

Doggust, Smaugust

September Art Challenges

Sketchtember, Swordtember

October Art Challenges

Catober, Inktober, Drawlloween, Drawtober, Peachtober, OC-tober

November Art Challenges

Slowvember, Huevember, Folktale week, Dinovember

December Art Challenges

Childhood week, Drawcember

Coloring Challenges

Most Popular Get My Popular Procreate Brushes

Join 1000s of artists and get my custom-made Procreate brushes - 🎨 Watercolor Brush Set, 🖌️ Gouache Brush Set, ✏️ Sketching Brush Set, and more ...

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3 Marker Challenge

Make an artwork using only three markers to practice constraint, values, and layering.

• 🌐 More info at Three Marker Challenge

Huevember

Make one piece per day in November focused on a single hue to deepen color control.

• 🌐 More info at matthieudaures.tumblr.com

Drawing and Sketching Challenges

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7-Day Urban Sketching Challenge

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7-Day Urban Sketching Challenge with Prompts

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Join me in the 7-day urban sketching challenge, where we will go on an adventure of traveling through art. You will learn a fun and easy way to create quick sketches and colorful scenes inspired by beautiful locations while developing positive drawing habits.

6 Minute Daily Sketch Challenge

Set a strict six-minute timer for one drawing a day to build speed and decisiveness.

• #️⃣ Hashtags #6minutesketch

20 Art Styles Challenge

A very popular, if somewhat difficult, art challenge, 20 Art Styles, asks you to draw the same character in 20 different styles.

• #️⃣ Hashtags #20stylechallenge and #20styles

Art Journal January

Fill your art journal daily in January with quick prompts to loosen up after the holidays.

• 🌐 More info at Kick in the Creatives website.

Catober

Draw cats every day in October to practice poses, expressions, and fur.

• #️⃣ Hashtags #catober and #catober2025 (or the current year).

Doggust

Create a dog drawing each day in August to practice gesture, fur, and breed variety.

• 🌐 More info at instagram.com/dogsinaugust/

Dinovember

Draw a dinosaur daily in November to study anatomy, texture, and prehistoric forms.

• 🌐 More info at Dinovember website

Drawtober

Follow curated October prompt lists to produce polished, narrative-leaning spooky pieces.

• 🌐 More info at drawtober.com

Drawcember

Close the year with a drawing a day in December to finish strong and test new ideas.

• #️⃣ Hashtags #drawcember and #drawcember2025 (change year)

Drawlloween

Make a Halloween-themed piece each day in October for spooky, playful practice.

• #️⃣ Hashtags #drawlloween2025 (with the current year) or @drawlloween
• 🌐 More info at drawlloween.blogspot.com

Draw 50 Things

The idea is to draw a picture that tells a story, has at least one character, and also has at least fifty other identifiable objects! 

• #️⃣ Hashtags #draw50things

Draw This Again

Draw This Again is an art challenge that asks you to find an old piece you have drawn, inked, painted, digitally rendered, or made in any medium and do it again.

• #️⃣ Hashtags #drawthisagain
• 🌐 More info at boredpanda.com/draw-me-again-improved-skills

Draw This in Your Style

Draw This in Your Own Style is an art challenge where an artist posts artworks, often OC (original characters), and asks you to redo them in your medium of choice.

• #️⃣ Hashtags #drawthisinyoustyle #dtiys
• 🌐 More info at drawthisinyourstyle.com

Magical March

Every day in March, you draw a magical girl character. 

• #️⃣ Hashtags #magicalgirl or #magicalmarch

Mermay

Draw or paint a mermaid every day in May to practice anatomy, water effects, and narrative.

• #️⃣ Hashtags: #mermay, #mermay{year} (#mermay2025)
• 🌐 More info at mermay.com.

Check out my interview with Holly Fae who paints Mermaids, here: Ep.195: How to implement art in business with Holly Fae

Junicorn

Draw a unicorn every day in June to practice stylization and magical themes.

• #️⃣ Hashtags: #junicorn
• 🌐 More info at freepik.com

Peachtober

Use Furry Little Peach’s cozy October prompts for charming, low-pressure daily art.

• 🌐 More info at peachtober website

Sketch Dailies

A simple Twitter-based daily art challenge, Sketch Dailies posts a new prompt every day, from which you are asked to come up with your own daily sketch.

• #️⃣ Hashtags: #Sketch_Dailies or @Sketch_Dailies2025 (change year)
• 🌐 More info at twitter.com/Sketch_Dailies

Sketchtember

Commit to a sketch a day in September to strengthen fundamentals without the pressure of finishes

• 🌐 More info at Sketchtember website

Slowvember

Spend the month on one thoughtful piece to level up planning, depth, and finish.

• #️⃣ Hashtags: #slowvember

Check out my interview with Jake Parker (the creator) here: Ep.22: Finished, not Perfect with Jake Parker

Speed Drawing Challenge

The challenge asks you to draw a character in 10 minutes, then again in 1 minute, and finally, the same character in only 10 seconds.

• #️⃣ Hashtags: #10minutes1minute10seconds, ️#speeddrawing, #speedpaint

Swordtember

Design a new sword daily in September to hone shape language, motifs, and worldbuilding.

• #️⃣ Hashtags: #swordtember

Character Design and Drawing People Challenges

Featured Course Learn to draw people by using simple shapes

Join me in the class, where I take you through the journey of designing characters using simple shapes, so you get more comfortable and have a solid starting point when drawing characters for your illustrations.

Click Here To Learn More

100 Heads Challenge

Draw 100 heads as quickly as is sustainable to sharpen proportions, planes, and likeness.

• #️⃣ Hashtags: #100headschallenge.

Ahmed Aldoori started the 100 Heads challenge. Check out my interviews with him:

• Ep.39: Ahmed Aldoori on Talent and Discipline
• Ep.194: What’s new with Ahmed Aldoori

Figuary

Daily figure-drawing videos/prompts by Love Life Drawing & New Masters (formerly Croquis Cafe). Great for gesture discipline.

💡 Find my recommendations for more Pose references here

Character Design Challenge

Interpret a monthly theme with an original character under clear rules and deadlines.

• 🌐 More info at characterdesignreferences.com/challenge-rules.

Creatuanary

Draw a new creature every day in January to explore anatomy, shape design, and imagination.

• 🌐 More info at Creatuanary website

February Faces

Create a portrait each day in February to practice features, skin tones, and likeness.

• 🌐 More info at kickinthecreatives.com/february-faces.

From A to Z!

Work through alphabet-themed daily prompts in January to rebuild momentum with simple subjects.

• 🌐 More info at DoodleWash A to Z Challenge page.

Julycanthropy

Draw werewolves all July to experiment with creature anatomy and transformation.

• #️⃣ Hashtags: #julycanthropy

Kaijune and Kaijuly

Design a giant monster each day in June and July to push scale, silhouette, and environment.

• #️⃣ Hashtags: #kaijune, #kaijuly
• 🌐 More info at kaijune.tumblr.com

March of Robots

Draw a robot every day in March to practice hard-surface forms and design language.

• 🌐 More info at chocolatesoopstudio.com

OC-tober

Develop an original character with daily October prompts to build personality, wardrobe, and story.

• 🌐 More info at OC-tober website

Sailor Moon Redraw

Redraw a classic Sailor Moon still in your style to test stylization and likeness.

• #️⃣ Hashtags: #sailormoonredraw

Six Fanarts

Take six prompts from your audience and draw six fan characters to practice versatility.

• #️⃣ Hashtags: #6fanarts or #sixfanartschallenge
• 🌐 More info here.

Smaugust

Draw a dragon every day in August to develop scale, texture, and fantasy design.

• #️⃣ Hashtags: #smaugust

Toon Me

Take a selfie and then render half of your face in toon style. 

• #️⃣ Hashtags: #ToonMe, #toonmechallenge

Witcher

#witcherOC designates artists’ visions of original characters which might appear on the TV show, while #witcherlass is for original artwork depicting female witchers.

• #️⃣ Hashtags: #witcherOC and #witcherlass 

Wizardapril

Illustrate wizardly themes all April to play with character design, props, and spells.

• #️⃣ Hashtags: #wizardapril

Learn more about Nathana (the challenge creator) in my interview: Ep.124: How to get paid for doing what you love with Nathanna Erica

Photography Challenges

30-Day Photo Challenge

With an especially creative prompt list and vivid explanations of each prompt, this is a great art challenge for any artist who wants to shift their focus or for photographers who just need a little inspiration.

• #️⃣ Hashtags: #fff30
• 🌐 More info at footprintandfancyfree.com/30-day-photography-challenge

365 Day Photo Challenge

Take a photo every day for a year following prompts to improve composition and seeing.

• #️⃣ Hashtags: #365daysphotochallenge
• 🌐 More info at expertphotography.com/365-photo-challenge-calendar.

Creativity and Inspiration Challenges

NEW Join Art Club with Iva

🤩 Join Art Club with Iva for access to popular PROCREATE classes, tutorials, my drawing process, references, Procreate brushes use inspiration, and more.

Click Here To Learn More

100 Day Project

Pick a focus and make something small every day for 100 days to build consistency. Use

• #️⃣ Hashtags: #the100dayproject
• 🌐 More info at the100dayproject.org

Childhood Week

For one week in June (and again in December), illustrate prompts inspired by childhood memories. 

• #️⃣ Hashtags: #childhoodweek or #childhoodweek2025 (current year, of course)
• 🌐 More info at beatriceblue.net/childhood

Check out my interviews with Bea (the creator) here:

• Ep.71: How to make the best out of every situation with Bea Blue
• Ep.206: Beatrice “Bea” Blue on the importance of enjoying the journey

Different Art Styles Challenge

Using a 9-square template, you are asked to draw a character (including yourself) in 9 different styles, such as Disney, Simpsons, Tim Burton, or whatever you’d like.

• #️⃣ Hashtags: #stylechallenge

Folktale Week

Illustrate one folklore-inspired prompt each day for a week in November to strengthen storytelling.

• 🌐 More info at Folktaleweek Instagram

Left-Hand Challenges

Draw something with your dominant hand and then draw the same thing with your other hand. 

• #️⃣ Hashtags: #nondominanthanddrawing 

Doodlewash

Follow gentle monthly sketch/watercolor prompts any time of year for daily practice.

• #️⃣ Hashtags: #doodlewashjune2025 (change month/year), #worldwatercolorgroup
• 🌐 More info at doodlewash.com

Faerie February

Design or illustrate a different fairy each day in February for whimsy, costuming, and story.

• #️⃣ Hashtags: #faeriefeb and/or #faeriefebruary
• 🌐 More info at faeriefebruary.com

Fauna Focus

The Fauna Focus art challenge brings a new animal into the spotlight every month and asks you to create artwork based on or inspired by that particular animal.

• #️⃣ Hashtags: #faunafocus
• 🌐 More info at faunafocus.com

Munchy May

Create food-themed art all May to explore forms, textures, and appetizing color.

• #️⃣ Hashtags: #munchymay and #munchymay2025 (change year)
• 🌐 More info at Munchy May Instagram page

Tic Tac Toe Challenge

Using a prompt sheet as a tic tac toe board, this weekly challenge asks you to select a horizontal, vertical, or diagonal line and use those three prompts to craft a new piece.

• #️⃣ Hashtags: #tictactoechallenge
• 🌐 More info at tictactoechallenge.com

Tinker Labs 12 Months of Art Challenges

The 12 Months of Art Challenges gives a new word prompt every day of the year, for a total of 365 word prompts.

• #️⃣ Hashtags: @tinkerlab or #tinkersketch
• 🌐 More info at tinkerlab.com/art-challenges

Painting Challenges

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Join Evolve Artist Program, the world’s simplest art training method with results guaranteed!

Click Here To Learn More

World Watercolor Month

Make a watercolor each day in July using official prompts to celebrate the medium.

• 🌐 More info at worldwatercolormonth.com

PleinAirpril Art Challenge

Paint or sketch from life daily in April to train observation, color, and light.

• 🌐 More info at Warrior Painters website

Abstract Art Challenge

This is not a social media art challenge like most others but a personal one you can take on to work in a different style, challenge yourself and develop your painting skills.

• #️⃣ Hashtags: #abstractart
• 🌐 More info at cghatcher.com/42-abstract-concepts-to-paint

Daily Paintworks Monthly Challenge

Enter weekly/monthly painting prompts and contests to build cadence and get feedback.

• 🌐 More info at dailypaintworks.com

Fox and Hazel 30-Day Watercolor Challenge

Follow a friendly 30-day prompt set to learn watercolors basics and flow.

• #️⃣ Hashtags: #foxandwatercolour
• 🌐 More info at foxandhazel.com

The Critique Me Challenge

Posting your work on this art challenge will let you receive constructive criticism and advice from the site’s community of artists. 

• 🌐 More info at dailypaintworks.com/challenge/the-critique-me-challenge/14.

Artist Promo Challenges

Most Popular Get My Popular Procreate Brushes

Join 1000s of artists and get my custom-made Procreate brushes - 🎨 Watercolor Brush Set, 🖌️ Gouache Brush Set, ✏️ Sketching Brush Set, and more ...

Click Here to Get the Brushes

ArtVsArtist

Build a 3×3 grid with eight artworks around a center selfie to showcase your style at a glance.

• #️⃣ Hashtags: #artvsartist
• 🌐 More info at instagram.com/explore/tags/artvsartist

March Meet the Maker

Share weekday posts in March that tell the story of your art practice, process, and values.

• 🌐 More info at marchmeetthemaker.com

Face Your Art Challenge

Make a 3×3 grid of cropped faces from your work to analyze consistency and stylistic quirks.

• #️⃣ Hashtags: #faceyourartchallenge
• 🌐 More info at www.chaoillustrations.co.uk

Portfolio Day Challenge

Post your best work on the quarterly hashtag to get your portfolio in front of clients and peers.

• 🌐 More info at portfolioday.art

Most Popular Art Challenge

Limited Time Offer Get Training You Need to Create Amazing Art

Join Evolve Artist Program, the world’s simplest art training method with results guaranteed!

Click Here To Learn More

Inktober

Create an ink drawing each day in October using official prompts to improve line, contrast, and discipline..

• #️⃣ Hashtags: #inktober and #inktober2025 (change year)
• 🌐 More info at inktober.com

Also, check out my recommendations for artist inks & supplies: Best Artist Inks in 2025

Check out my interview with Jake here: Ep.22: Finished, not Perfect with Jake Parker

Crafting Challenges

Just Add Ink Crafting Challenge

Join weekly cardmaking prompts to explore layout, stamping, and paper techniques.

• 🌐 More info at just-add-ink.blogspot.com/search/label/Challenges

Paper Craft Crew Challenges

Try weekly paper-craft challenges that emphasize sketches, color combos, and themes.

• 🌐 More info at papercraftcrew.com

Check out my interview with “Paperwolf” here: Ep.43: Wolfram Kampfmeyer (Paperwolf) on how to succeed on Etsy and Dawanda

The Paper Players Crafting Challenges

Participate in weekly themed papercraft prompts to practice design and finishing.

• 🌐 More info at thepaperplayers.blogspot.com

TikTok Art Challenges

TikTok art challenges are great for staying creative and growing your audience fast.

To get the most out of them:

• Pick a visual challenge like DTIYS, Peachtober, or 3-Marker
• Film a short timelapse (under 30–40 sec works best)
• Overlay simple text: challenge name, day number, and your medium
• Use 2–3 focused hashtags (challenge tag + your tool, e.g., #dtiys #procreate)
• Pin a comment with your brushes or materials—viewers love it
• Stitch or duet the original prompt card for extra reach
• Keep your hook simple: “Day 5 – Witch Hat” or “My version of this DTIYS!”

Quick, clear, and watchable wins every time. Let the art speak.

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Hi, I am Iva (rhymes with “viva”). I am a full-time self-taught artist behind Art Side of Life® and a Top Teacher on Skillshare. I have 15 years of experience in the creative field as a concept designer, illustrator, art director, and now freelance artist, content creator, and art instructor. My goal is to help you get your creative groove on with Procreate and make awesome art through practical classes, tutorials, Procreate brushes, and guides on art tools, supplies and resources. About me »

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