Easy as Pumpkin Pie: How to Paint a Pumpkin

September has just closed its doors for another year, and as we drift into October and the Halloween season, it’s hard to contain my excitement for everything this holiday has to offer. Eating pumpkin desserts and dishes, stepping through colorful and crunchy fallen leaves, and feeling the wind whisper of winter are some of the things I love.

For several years now, my family has celebrated all of this at our “Fall Family Fun Fest,” which includes carving pumpkins together. But that’s a few weeks away and I’m biting at the bit to get started. It’s way too early to carve jack-o-lanterns just yet, as they’ll surely rot before Halloween, so I decided to try something just as fun and creative: painting pumpkins.

When you choose a pumpkin to paint, make sure the surface is smooth and firm. You can find a pumpkin with an interesting stem and incorporate that into your design as well. My plan was to paint three pumpkins, each with an initial for "Haas Family Vineyards,” which I manage as one of my hobbies, and stack the pumpkins on top of each other to display. I was going to use the miniature orange pumpkins that are so adorable, but while shopping, these tiger striped pumpkins caught my attention. They were more ideal because they were flat and slightly bigger, and the stems were short enough to make stacking easy them easy. I’m a pretty big fan of nature, and so I have to admit here that it was slightly difficult to paint over the beautiful patterns that these pumpkins wore so proudly (but I got over that, obviously).

For this project I used black acrylic paint, taking care to get plenty of paint in the space where the stem meets the pumpkin, but not getting any of it on the stem itself. I chose black because I’m so in love with the chalkboard look, and knew that I wanted the initials to be white to reflect this. The acrylic dried quickly, and because it was black, it was easy to see where I needed to go back over it with a second coat for any little spots I painted too lightly.

The initials stand for "Haas Family Vineyards." The style of the letters and the art were inspired by The Art of Whimsical Lettering by Joanne Sharpe. I kept the lettering simple because I was using a paintbrush (as opposed to a pen) and had a limited surface on which to paint. Using black and white paint gave the pumpkins the desired chalkboard effect that I was hoping to achieve. Click here to "pin" this!

Once the pumpkins were completely dry, I used white tempera paint to draw the letters. Here’s where it helps to use a reference for your design. You can draw anything you like (watch Tiffany Lovering’s video demonstration on how to tangle on a pumpkin), but consider what styles you find yourself using in your art journal, for example. Simply transfer that to the pumpkin, and you won’t be disappointed. That’s why I opened my copy of The Art of Whimsical Lettering by Joanne Sharpe. I refer to it often, and knew it would spark some ideas on how to draw my letters.

You could use a pencil to lightly draw your design onto the pumpkin surface, but I always like to freestyle my letters with the tempera paint. Take note that if you use tempera, keep your pumpkins dry afterward, as it’s not water resistant. Mine are now cozily tucked on my front porch, safe from the rain that’s sure to come at some point in October.

I hope you’ve enjoyed this Halloween project. Share your painted pumpkins and Fall-inspired art on our gallery page. I can’t wait to see what you come up with!

Happy Fall,




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