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Yearly Art Challenges

One thing you can always count on a creative for – is to have fun! Artists and creatives around the world have put out their own art challenges to bring together creatives from all corners of the globe. These range in theme, media, intent and inspiration!

We have selected the 10 Yearly Art and Drawing Challenges that are trending.


With October already in full swing, make sure to check out the Inktober Art Challenge! Founded by Jake Parker, Inktober is based on promoting growth, improving your skills and sharing your work with fellow artists. Each year, Inktober puts out a prompt list that you can follow throughout the month. These serve as your inspiration and hopefully get your creative flow going! There aren’t too many rules, with the main one being that you have to use ink. Share your work on social media using the hashtag #Inktober #Inktober2020.

Inktober 2020 prompt list
Source: Inktober.com

For more art challenges running during the month of October check out our article about other art challenges in October you can participate in. If you're curious to the best artworks of Inktober 2020, make sure to visit this page.

Draw this again

Although this challenge doesn’t run for any particular month of the year, its perfect for finding out how much you’ve progressed as an artist. Select one of your artworks from the past year and recreate it!

By doing this, you’ll be able to compare how much you have either improved or changed over the last year. Make sure to redo this challenge each year and create a visual interpretation of your journey as an artist. Seeing great progress will undoubtedly serve as a great source of inspiration!


The MerMay art challenge asks artists to create artworks of mermaids every day during the month of May. There is no restriction regarding which media should be used, only that the mermaids and mermen theme is followed.

The challenge was created by the incredibly talented Disney animator Tom Bancroft. Each year, a new prompt list is put out. Check out this year’s prompt list for MerMay 2020 and make sure to use the hashtag #MerMay when sharing your illustrations on social media. 

MerMay art challenge prompt list

100 Heads Challenge

This challenge can be taken at any point during the year, and lasts for 10 days. The challenge itself was created by Ahmed Aldoori. The goal of this challenge is to sketch 100 heads or portraits during the time limit. It serves as a great way to practise drawing faces, which can be an incredibly difficult part of the body to draw!

You can watch his version of the #100HeadsChallenge below:


Unlike any of the other challenges that we’ve mentioned, this challenge isn’t about working on your skills or seeing your progress – it’s about sharing the face of the artist behind the art. This challenge is incredibly popular on social media.

The collage template (psd) can be found here and features 8 blocks for your artwork and one extra centre block for a portrait of you! This challenge aims to create a space in which you can introduce yourself to your followers. Make sure to use the hashtag #ArtVsArtist when sharing your completed templates.

Toon Me

Another great way to introduce yourself to your followers is the Toon Me art challenge. The challenge was created by René Córdova, a Marvel illustrator. One day, he decided to post a picture on Instagram that was split in half – one was a [selfie] picture of himself, and the other was an illustrated, cartoon version of the other half of the picture. And so the challenge was born! Make sure to use the hashtag #TuneMe and #Toonme when sharing your work!


This November based challenge is a sure favourite, with daily hues as prompts! Each year a new prompt ‘list’ is put out for creatives to take inspiration from. The challenge itself was started by Matthieu Daures on Tumblr.

The ruled are limited – make sure that the featured hue for that day is the main colour of focus in your artwork. You are free to use whatever other colours you’d like. There are also no limitations regarding medium – so have fun!

What is Huevember - Prompt List
What is Huevember – Prompt List

Make sure to use the hashtag #Huevember when sharing your work online.

For more about the challenge you can visit https://facebook.com/huevember/ or https://huevember.tumblr.com

Daily Sketch for a Year

This challenge is maybe one of the most difficult challenges we’ll be mentioning in this article. The title itself is pretty explanatory – the challenge urges participants to do a sketch every single day, without any skips, for a year.

There will undoubtedly be days where you feel unmotivated or uninspired, and these will be the days that challenge your dedication as an artist. There are no rules regarding theme or medium for this challenge – that’s all up to you. Set your expectations, goals and skills you want to work on in the coming year and get sketching!

Draw this in your style

Although fairly new to the art challenge scene, #DrawThisInYourStyle has become increasingly popular. The challenge is run by a number of artists who put out an original artwork and urge their followers to recreate the piece in their own unique style. The rules for this challenge vary between artists and could include colour, time or medium limitations.

Each challenge has their own hashtag, so make sure to check which one to use when sharing your recreations online!


Running during the month of August, this 30 day challenge is based on the theme of dragons. Within the art community, August is the month of dragonsSmaugust. Everyday during this month, you’ll be required to create dragon themed artwork using whatever tools, medium or style you prefer.

There are a number of prompt lists available, so make sure to take a look through them to find the one that inspires you most! Make sure to use the hashtag #Smaugust when sharing your art on social media.

Art challenges we missed

Did we cover all art challenges? Did we miss one? What are your favourite art challenges? Let us know, we love to hear from you. Leave a comment below or contact us and we will add them here.

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