How to Drill Pumpkins for Spooky Wooden Snakes

Just to be clear, the post title is meant to be read in a Dr. Dre–style cadence, like that classic song (I still jam the clean version sometimes). Now that that’s out of the way, let’s talk about something hardcore: pumpkins.

This year we found some lumpy, bumpy orange-red pumpkins instead of the usual smooth yellow-orange types. The coolest thing about them was that each had a stem at the top and bottom, which felt delightfully quirky. As soon as we brought them home we started hollowing them out. I asked John to carve a serial-killer style face (for the record, I always type “cereal killer” first and have to backspace) and he nailed the creepy look—mission accomplished.

And the pumpkin seeds? Gone. They were devoured long before the photos were even uploaded. That probably says more about our snack priorities than our blogging speed, so I’ll just admit we were hungry and leave it at that.

Scoop, there it is.

After hollowing both pumpkins, we broke out some power tools. Yep, these pumpkins were getting hardcore treatment. The idea actually started a few nights earlier when we were thinking about Halloween before bed — not anything weird, just brainstorming pumpkin ideas. We talked about doing something wormy for our daughter who loves gummy worms, carving multiple holes so worms could look like they were oozing out. Then we remembered the wooden craft snakes I painted last year.

Since Clara loves those wiggly snakes as much as worms, we realized we could combine them with the pumpkins for a snake-themed display. We used a smaller drill bit to make neat, snake-sized holes, and I loved the little ribbons of pumpkin that curled away as the drill bored through the thick flesh.

When the snakes were poked into place the pumpkins suddenly looked tough and a little sinister—like something you wouldn’t want to meet in a dark alley. We snapped some close-ups to capture that vibe.

One pumpkin looked particularly gnarly: wart-like bumps, two stems, and snakes slithering from the openings. A ceramic crow perched above it for dramatic effect. It all felt playfully ominous, like a tiny theatrical scene of bad luck for Mr. Pumpkin.

The other pumpkin was similarly holed and filled with snakes. Together they made for a compact but effective spooky display.

I couldn’t resist rearranging our block letters that normally spell LOVE to read EVIL instead. Years ago I’d drawn an “I” on the back side of the O, so a quick shuffle did the trick. I added a few ceramic critters for atmosphere—classic Halloween companions to the pumpkins and snakes.

The ceramic animals really completed the scene. A frog with a bumpy texture matched the pumpkins’ warts, a crow added a sinister silhouette, and even our white ceramic rabbit—normally sweet—looked unexpectedly fierce among the tougher accents. It’s kind of fun to let him take a one-night walk on the wild side before he resumes his more innocent role the rest of the year.

I briefly considered painting dripping red “blood” across the LOVE block, but that would be permanent. Instead I might cut red letters from construction paper and stick them on temporarily, or simply leave the uplifting message peeking out above the spooky vignette. There’s a nice contrast in letting the cheerful sentiment hover above the creepy tableau.

We also still plan to frame the photos of our skullified faces (something we made in Photoshop a few years back) and tuck them into our hallway gallery. That piece makes a seasonal reappearance every year, and we enjoy sneaking it into the frame grouping and seeing who notices.

Speaking of Halloween ideas, we’ve collected nearly a dozen seasonal posts on our Holiday project page with plenty of inspiration—everything from puffy-painted pumpkins and playful monograms to batty décor and dramatic candles. If you’re looking for crafty ways to spook up your home, there’s a lot to choose from.

What are you doing to make your home spooky this year? Are you using ceramic critters and a power drill? If not, I strongly encourage you to consider it. It’s a quick way to take ordinary pumpkins into delightfully creepy territory. Mic drop.

P.S. John misses you and apologizes for being quiet here lately—he’s been busy polishing a PowerPoint for our talk in Cincinnati this weekend. He’ll pop in later and tomorrow with more posts for you!