The Challenge: Make Art Everyday

Welcome to the month-long celebration of arts and creativity of ARTober. Art challenges with daily practice help improve your drawing and observational skills and help kick-start flagging inspiration or creativity. Throughout October, there are classes, drop-in, and pop-up events to help you reach your goal of creating something every day.

But wait, what is art?

Art is the creation of something new. It can be a drawing, painting, sculpture, video, photography, carving, writing, or almost anything!

You don’t need special tools to make art!

Much of ARTober focuses on drawing with paper with pens or pencils since those are supplies most people already have on hand. ARTober is about getting past barriers to making art and is not limited to specific tools requirements.

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The Latest Additions to the ARTober Gallery

ARTober Prize Drawing

It’s not a pun, it’s an actual prize drawing! Throughout ARTober you can submit photos of your daily artwork by email to (or use the upload form) to enter to win an Artist-Supply-Bundle for Adult/Teen or Youth categories. Every piece of art you submit will be another entry in the drawing, up to one a day for all thirty days. The winners will be chosen randomly from all entries received.

Adult/Teen Prize

Youth Prize

Submit your art for the Artist Bundle Drawing

Files accepted: jpg, jpeg, png, gif

ARTober Drawing Prompts

Drawing Prompts Week One, October 1 – 7

  1. “Single Line”:  Draw from looking at an object, other art, or photograph (up the challenge for trying this as self-portrait!) and do not raise your pencil or pen from the paper until you feel you are done.
  2. “No Look”: Draw from looking at an object, other art, or photograph (bonus points for trying this as a self-portrait!), and don’t look at your paper if you can help it. You can combine this with “Single Line” prompt and as a self-portrait for the ultimate challenge.
  3. “Timing is Everything”: Choose an object of some amount of complexity, for example, a fancy teacup on a saucer half-filled with tea, a tea bag hanging over the side, teaspoon next to it. Separate your page into multiple areas, at least six. Draw that object by the time you count to twenty seconds. And do that same object in each of the six areas. Notice your approach each time when you don’t have too much time. Do you start the same way every time when the clock is ticking?
  4. “Names/Words”: Draw your name or a single word several times, each time using only blocks, only swirls, only circles, or only dots (the latter is my favorite).
  5. “Everything But”: position yourself a distance away from a kitchen chair or other chair with legs or another object that has ‘holes’ where you can see through it. Then, draw everything but that object, as if it was the same color as your paper.
  6. “Outside Free Choice”: go outside, sit and observe your surroundings for ten whole minutes (set a timer!), picking and examining an object or part of the scenery to draw, then draw that object.
  7. “Circles”: fill a page with circles. You choose the size of the circle, color, the thickness of the line. Fill in the whole page.


“They Pick/Random Pantry”: Ask a family member or friend to suggest something to draw, then draw what they pick. If your family is asleep or out to dinner then close your eyes, open your pantry, and point your finger. Open your eyes and draw whatever you were pointing at.

Drawing Prompts Week Two, October 8 – 14

  1. “On the Other Hand”: You probably saw this one coming. First, draw your choice of an item with your non-prominent hand. If this isn’t possible due to injury or other reasons, use your prominent hand but choose a non-typical grip. Alternate: hold a pen/marker that doesn’t require pressure from the barely-there tips of your fingers.
  2. “Freeze Frame”: Watching media of your choice: TV, movie, video, etc., pause the video and draw what is on the screen until the device dims or goes to sleep and blacks out the screen.
  3. “By the Cover”: Redraw the cover of your favorite movie, book, coloring book, music CD, or magazine, etc.
  4. “Mirror Universe Clone”: If you’re using a sketchbook, skip ahead a page and lay the book flat; if you’re using a regular sheet of paper, fold it in half. Draw on the right-hand page of the sketchbook or right-hand side of the folded page. Then redraw the contents of the right page onto the left page but mirrored.
  5. “Conceptual Time Lapse”: As a single drawing, draw an apple growing into an apple tree.
  6. “Beholder”: Using a mirror, or a photo closeup, draw a closeup of your eye.
  7. “Wait, Was it a Hectagon?”: Draw from memory all the road signs you can think of and/or all road signs you can see from the windows of your home.

Drawing Prompts Week Three, October 15 – 21

  1. “Fresh Start”: Draw your breakfast (before you eat it?).
  2. “In the Wild”: Draw the next animal you see.
  3. “Change Your Perspective”: Draw something from a picture reference material (magazine or printed picture, etc.) but draw it upside down.
  4. “Looking Good”: Draw your favorite outfit.
  5. “Closer”: Pick something to draw; the previous pantry challenge is a good start, then zoom in to draw a second detailed area of that drawing, then zoom into that detailed drawing and draw that as your third work.
  6. “It’s Your Birthday”: Draw your cake or dessert. Perhaps a cake from memory that was your favorite, or the dream cake you have yet to eat.
  7. “Gray Days”: Umbrellas and the rain.

Drawing Prompts Week Four, October 22 – 28

  1. “Fall Leaves”: Gather a bunch of freshly fallen leaves and create a small pile on a table. Provide as dramatic lighting as possible to create deep shadows in the leaves, twists, and drying shapes to draw.
  2. “Random Photo”: Scroll through your digital (or physical) photo album and pick a photo from the feed without looking. Draw that photo.
  3. “Set Your Alarm”: Set your alarm for a random time later in the day and keep your sketchbook with you. Then, when the alarm goes off, draw what you were looking at.
  4. “ARTober poster color”: Pickup an ARTober screen-printed poster in the Studio at the Winnetka Library. Color the poster with media of your choice; the paper is heavy enough to handle watercolor or most markers.
  5. “Coffee, How About More Coffee? Or Tea?”: Draw your coffee, tea, or beverage.
  6. “Everything is Coming Up Mushrooms”: Count how many pictures you have submitted for ARTober, draw that many mushrooms. If you haven’t submitted any images, draw one mushroom and submit that drawing for the gallery. It’s not too late to start.
  7. “Through the Looking (Water) Glass”: Fill a clear glass with water, place an object behind the glass. Draw the item and the glass as it distorts the light and shape of the object.

Drawing Prompts Last Three Days, October 29 – 31

  1. “Thoughts?”: Do a piece of art in any media to symbolize how ARTober has felt to you. Joyous, challenging, etc.: try to capture that feeling. Alternate: make your very own ARTober promotional poster or incorporate ‘ARTober’ in some way.
  2. “Sincere Flattery “: Pick someone else’s work from the ARTober gallery and copy it.
  3. “And Back Again”: Recreate your first ARTober work, these 30 days later.

Select books on Art and Drawing

For The Younger Artists