6 Great Drawing Challenges

✏️ Drawing Challenges for Middle & High School

These aren’t quite full-blown lessons, and they’re definitely more than just casual sketchbook prompts—these are our favorite go-to drawing challenges.

We pull these out when we need something fresh, creative, and engaging that still leads to awesome results. They’re low-prep, easy to adapt, and perfect for sub days, early finishers, or days when you want to focus more on creative problem-solving than technical perfection.

Some of our classroom favorites:

• 🌀 Inked Zentangles – Always a hit. Once they start inking, they can’t stop. We keep tons of variations and worksheets in our store to keep it fresh.

• 🎀 Ribbon Animals – A twist on contour and gesture drawing—students turn animals into flowing ribbons to explore line, shape, and movement.

• ✏️ #2 Pencil Morphs – Transform a plain yellow pencil into a wild object or animal. It’s tougher (and funnier) than it sounds. A great thinking cap exercise.
  

  

  

  

  

  

  

• 🧃 Deconstruct-an-Object –  I’ll sometimes grab a bulk supply of something random (like styrofoam cups) and hand one out to each student. Their job? Deconstruct it and turn it into a drawing. It’s abstract, observational, and creative all at once.
  

• 🖼️ Art History Memes – Students turn classic paintings into modern memes. Equal parts hilarious and sneakily educational. Check out our set in our shop:

• 🔄 Morphing Drawings – Start with one object or animal and morph it into another in a series of 3–5 steps. These are so fun to look at when finished—sometimes weird, always awesome.

These challenges stretch creative thinking while giving students structure. They’re short, satisfying, and approachable, which means everyone from your hesitant drawers to your advanced students can dive in and make something they’re proud of. It also lets them practice fundamentals (line, shading, form) in non-traditional and playful ways. And bonus? They're perfect for building out a sketchbook or rotating classroom displays.

📌 Check out our store for printable drawing challenges, resources, and variations for all levels!

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