What’s Your Best Guess?

 —Stephanie Shapiro has been a Market regular for nearly 40 years. She lives in Tuxedo Park with husband Tom and dog Archie.

If it’s October, it’s time for the Market’s annual Guess the Weight of the Giant Pumpkin contest—a favorite Market tradition that dates back decades. Writer Stephanie Shapiro interviewed key persons involved in the contest, which will be held this year on Hallowe’en, Saturday, October 31. The contest is free, costumes are optional, and there are prizes!

Come summer, when his Prizewinner pumpkins reach soft-ball size, Billy Caulk may place two or three on top of the straw bed where he’s planted them. That gives those pumpkins better odds to stay pest-free and grow to become shapely, plus-size contenders for the 32nd Street Farmers Market’s annual pumpkin weight guessing contest.

Otherwise, Billy doesn’t favor his most promising pumpkins with extra nutrients or lighting. “I hate to bust your bubble, but I don't do anything real special. I just plant a short row of them and hope for the best,” he says. Once the pumpkins ripen, “What I try to pick for the market is something that’s symmetrical and then, of course, it’s gotta keep.” 

Market manager Marc ‘Vernon’ Rey started the tradition in the 1990s. Every fall since, Billy has delivered his biggest, most comely and healthy pumpkin to the market, where kids of all ages are invited to guess its heft. Prizewinner pumpkins generally weigh in the low triple digits, no competition for the Atlantic Giant, which in 2025 set the United States’ record at 2,749 pounds at the Safeway World Champion Pumpkin Weigh-off in California. (Billy’s biggest pumpkin to date topped 206 pounds.) But with its side-show, old-timey appeal, the 32nd Street contest is part of a tradition as American as … well, you know.

On this year’s contest day, October 31, the pumpkin is displayed state fair style amid hay bales and mini pumpkins. Ralph Stoddard, a market regular and pumpkin contest  volunteer, stands ready with clipboards, entry forms and pens in hand. Carnival barker for a day, he entices crowd members to enter their guess. Hundreds take him up on the offer. 

One year, Ralph observed a family of three who each took a guess using their own method. “It’s interesting watching if you have a husband and wife and a kid, because you get three different answers and three different processes,” he says. Answers can differ widely. In 2024, contestants’ guesses ranged from 25 pounds to one ton although the pumpkin in question weighed 145.5 pounds. The 2023 contest saw a three-way tie for second place and a two-way tie for third. That same year, a young girl ran away with first place. 

No matter the preferred method for estimating a pumpkin’s weight, the contest is a catalyst for community, Ralph says. “It’s the farmers market and you’re asking about pumpkins and nobody cares what political party you are. Everybody can do it.”