By Matt Crossman, Photos by Sam Fink

Photo courtesy of Sam Fink

I pushed open the window, and the loud wind rushed in, cold against my face. Far below me, rural northern St. Charles County rushed by. Far ahead, a giant X marked the spot.

As my friend Dan Hartman flew us toward the target on the grounds of the St. Charles County Regional Airport, I grabbed a pumpkin off of my lap, swiveled to my right, and dangled that gourd outside the plane. The dopey grin on my face—which had been present all day as I waited for my turn to throw pumpkins out of an airplane—grew ever larger. You couldn’t wipe that grin off all day: not before, not during, and not after I dropped three pumpkins in the broad vicinity of the X during the St. Charles County Flying Service Pumpkin Drop on the last Saturday of October. It was an epic, pointless, useless, absolutely no-real-world-relevance adventure, and I can’t recommend it highly enough.

The people on the ground had a blast, too. Hundreds of cars filled the parking lot, then the overflow lot, then the overflow for the overflow lot, according to Dennis Wiss, manager of St. Charles County Regional Airport–Smartt Field. The 13th annual pumpkin drop in 2021 was the most successful yet in terms of spectators (estimated at 800 to 1,000) and participants (51).

“Our big goal is to get youngsters involved in aviation,” Dennis says. To that end, a B-25 Mitchell and TBM Avenger were on hand, and kids were allowed to tour them, sit in the cockpits, and even go up for flights.

My goals going into the event were not lofty. Number one: Don’t fall out of the plane. Number two: See number one. I don’t think anyone’s goals were any grander than mine. As I waited in the hangar at St. Charles County Flying Service, I overheard one pumpkin bombardier say, “Just don’t hit your car and everything’s good.” Another pumpkin bombardier, Bob Becker, tried to find the best pilot to guide him into position so he could drop his pumpkin onto the X. He thoroughly grilled candidates, by which I mean he asked each of them: “Do you have a sense of humor?” One pilot cracked back, “I lost my funny bone years ago. It was an unfortunate pool accident.”

Bob owned a demolition company for decades and is known as Becker the Wrecker. He was as delightful to talk to as you would guess someone with that nickname who enters pumpkin-dropping contests would be. His wife, Naomi, bought him a spot in this competition as a birthday present. “What do you do for a 67-year-old guy these days?” Bob says. “You’ve got to do something fun.”

Back in the plane, I wondered when I should drop fall’s great orb. I have two friends who are fighter pilots, and both told me to drop the pumpkin earlier than I think I should. I did that … and missed by a ton. I dropped way, way too early. Then again, only six of the competitors hit the target, which was a 50-foot circle surrounding the X. We tied for last with 45 teams. 

“It’s strictly luck,” says Dennis Bampton, the owner of St. Charles Flying Service, which hosts the event. “We’ve had guys try to figure it out, using calculators and stuff. Get out of here. There’s no way.” Put another way: If you enter a contest in which you drop a pumpkin out of an airplane and care where it lands, you’re doing it wrong. Even if my pumpkin had landed halfway across Illinois, I still would have worn that big dopey grin all day.

The 2022 Event

The 2022 Pumpkin Drop takes place on October 29. Watch the St. Charles County calendar at for details.

This article also appears in the October 2022 issue of Missouri Life.