When it comes to carving pumpkins, most of us are happy if we manage a triangle-eyed jack-o’-lantern plopped on a porch or balcony. But for artist Rachael Kolby, who carves pumpkins for Night of 1,000 Jack-o’-Lanterns, pumpkins become artistic masterpieces.

Here’s how she does it.

Let’s start at the beginning. What’s your first pumpkin memory?

For me, pumpkins and Halloween have always gone hand in hand. Some of my earliest memories are of helping my family with the Halloween displays for our house. Like me, my dad was passionate about crafting and bringing spooky ideas to life. Every year, my sister and I worked with him to make everything from jack-o’-lanterns to scarecrows—even a remote-control spider to jump out and scare trick-or-treaters.

Us mere mortals are amazed at the masterpieces you create. What is the trickiest part?

Just about every part is tricky! When trying to create art out of fruit, it’s a wonder it ever goes right at all.

Pumpkins can have bumps, imperfections, rotten spots, or walls that are too thick or too thin for your design. Sometimes they don’t carve the way you expect or won’t light up properly. On top of that, you’re racing against time, so you must finish everything before they start to rot. All these challenges make pumpkin carving a delicate balance, which is part of what makes it so satisfying when it turns out well.

Once you start carving, I imagine there’s no turning back. Do you sketch your design first or go freestyle?

I like to plan my designs in advance to make sure everything goes smoothly. I’ll sketch out the artwork either by hand or on my computer and use that as a reference while carving.

However, I also try to stay flexible and improvise if something isn’t working out exactly as I imagined—it’s all part of the creative process!

Admittedly, it takes a while for most of us just to carve two triangle eyes and a half-moon grin in a pumpkin. How long does it take you to create your masterpieces?

The whole process can take me anywhere from 4 to 8 hours, depending on how complex the design is. This includes several steps such as sketching the design, prepping the pumpkin, painting if needed, and finally carving. Each step can vary in time based on the level of detail.

What’s the largest or most unusual pumpkin you’ve ever carved?

One of the most unique jack-o’-lantern carvings I’ve ever done was Jackson Pollock’s Number 8. It was for a show in New York a few years ago, and one of the themes for the event was “Famous Artwork.” While classics like the Mona Lisa and Whistler’s Mother were obvious choices, I half-jokingly suggested doing Pollock's piece. At first, the other artists thought it wouldn’t work because it was too chaotic. But I was determined to give it a try. I carefully rendered the splatters, taking the time to match them as closely as possible to the original. Ultimately, the crowd’s reaction was incredibly positive, and I felt like I achieved what I set out to do.

What design has gotten the biggest crowd reaction?

The first Baby Yoda jack-o’-lantern I carved, in 2020, was easily one of the most memorable and popular pieces I’ve ever made. It was after The Mandalorian debuted, and Baby Yoda (also known as Grogu) was becoming a cultural phenomenon. I created the carving right here at Chicago Botanic Garden, and the reaction was incredible. Kids were literally screaming, “It’s Baby Yoda!” and running toward it in excitement. Even adults couldn’t get enough of it.

Have you ever had a carving go totally wrong? What happened, and what did you do to fix it?

Yes, in 2018, I was working on a carving based on the cover art for Scary Stories to Tell in the Dark for a pumpkin trail event. What I didn’t realize at the time was that the pumpkin I’d used had gone completely rotten on the inside. The night before it was supposed to be displayed, it split open and smelled horrendous.

I was devastated, but I wasn’t about to give up on it. I stayed up all night re-carving the entire design from scratch on a new pumpkin. It was exhausting, but I was so proud of the finished product that it was worth the extra effort.

OK. The candy-obsessed people need to know. What’s your favorite Halloween candy?

I'm a big fan of dark chocolate. I really enjoy it when they make a dark chocolate version of a candy bar, like Milky Way Midnight or Dark Chocolate Kit Kats. But honestly, any Halloween candy that comes in a dark chocolate variety is a win for me!

If you weren’t carving pumpkins, what would you carve instead?

If I weren’t carving pumpkins, I’d probably explore other food art mediums, like cookie or cake decorating. I think it could be a lot of fun to sculpt chocolate or sugar, and I would still definitely find a way to incorporate spooky, Halloween-inspired designs.

What’s your favorite part about carving for Night of 1,000 Jack-o’-Lanterns?

I love getting a chance to get out of the studio and carve a pumpkin in front of the guests. It’s so much fun to connect with people who are enthusiastic and curious about the process. I love showing them that every single detail is done by hand, letting them see the process up close. Seeing their reactions makes all the hard work worthwhile and reminds me how much people appreciate the artistry that goes into making this amazing event come to life.