Think outside the pumpkin this fall season by painting pumpkins rather than carving. This is a great way to decorate your apartment for Halloween, and your pumpkin will last much longer. Not only is pumpkin painting kid friendly, it’s also much less messy! If your a fan of Da Bears, try this stylish Chi-Town-inspired pattern.

Pumpkin Painting Supplies

  • 1 pumpkin
  • Paint brushes
  • Navy Blue acrylic crafting paint
  • Orange acrylic crafting paint
  • White acrylic crafting paint
  • Chicago Bears Logo stencil
  • Ribbons (to tie around the stem for extra flair)
  • Q-tips
  • Nail polish remover
  • Masking Tape

Pumpkin Painting Instructions

Step 1: Pick your pumpkin. 

Pumpkins come in all shapes, sizes and colors. Any pumpkin will work perfectly for this project, so go ahead and choose your favorite. 

Pumpkin Painting - Choose a Pumpkin

Step 2: Choose a stencil.

The craft stores are full of different types of stencils. If you don’t see one that you like, do a search for an image and create your own stencil. Free handing your pumpkin image is always an option as well.  I chose to trace my logo from one of my favorite Bears shirts. 

Pumpkin Painting - Create a Stencil

Step 3: Position your stencil.

Select the spot on your pumpkin where you want you design to go and secure the stencil with masking tape. Try to pick the side of the pumpkin with the least imperfections. This will make your design come out more smoothly. Once you have your stencil positioned accurately, it’s time to start painting! 

Step 4: Get painting.

Fill in your stencil with the orange acrylic craft paint. Next, outline the “C” with white paint. Lastly, outline the white “C” with the navy blue acrylic paint. *Tip: If you smudge the paint or paint outside the lines, use a Q-Tip and nail polish remover for touch ups or remove any unwanted paint splatter. 

Pumpkin Painting - Paint with a Stencil

Step 5: Allow dry time.

Allow the paint to dry completely! If not, you risk having to start all over.

Step 6: Add finishing touches. 

Select a combination of ribbons to tie to the stem of your pumpkin. This is an optional step, but I think it adds a great personalized touch to your work of art!

Pumpkin Painting - Chicago Pumpkin

Have you done a pumpkin painting project? Send photos to for your chance to be featured!