Pumpkin Fest spans generations in Sycamore

62nd annual Sycamore Pumpkin Festival runs Oct. 25 through Oct. 29 in downtown Sycamore

Families get their pumpkins set up in the pumpkin display area Wednesday, Oct.26, 2022 on the DeKalb County Courthouse lawn during the first day of the Sycamore Pumpkin Festival.

SYCAMORE – Everybody’s got a childhood story, it seems, of chilly Octobers spent hauling decorated pumpkins to the courthouse lawn, playing carnival games and eating fair food, lining the streets to watch a parade before Halloween.

And more than six decades in, it’s not surprising, as Sycamore Pumpkin Festival has spanned multiple generations.

The 62nd annual Sycamore Pumpkin Festival runs Wednesday, Oct. 25, through Sunday, Oct. 29, in downtown Sycamore. It’s inarguably the city’s largest event of the year, one families have woven into their memories and traditions, said Cole Regnery, president of the Pumpkin Fest Committee.

“I moved to Sycamore when I was in the second grade. I’ve been involved in every festival since,” Regnery said. “I remember being a young child being fascinated by all the pumpkins on the courthouse lawn.”

Bronwyn Butler, 12, from Sycamore totes her heavy pumpkin into the pumpkin display area Wednesday, Oct.26, 2022 on the DeKalb County Courthouse lawn during the first day of the Sycamore Pumpkin Festival.

No one knows the festival’s legacy better, perhaps, than Jerry Malmassari of Sycamore. He’s been involved with the festival since 1964, according to Pumpkin Fest organizers. Malmassari was named this year’s Friend of the Festival and will get to ride in the parade. Malmassari has served eight terms as the Pumpkin Festival Committee president. He’s lived in Sycamore since 1963.

Calling Pumpkin Fest a family event for Malmassari seems, well, an understatement, organizers said. His daughter Julie, brother-in-law Rick, and niece, Jennifer, all have served as presidents. Malmassari’s youngest son, Joshua, also served on the Pumpkin Fest Board.

“I will always cherish the 36 years and the many committee members I served with. To my family, thank you for all your support. I truly hope all the not-for-profit participating groups and the community continue to appreciate, support, and enjoy the Sycamore Pumpkin Festival as much as my family and I have,” Malmassari said in a news release.

Jerry Malmassari was named Sycamore Pumpkin Festival's Friend of the Fest for 2023. He's been involved in the festival since 1964, organizers said.

The festival kicks off Wednesday, Oct. 25, with an opening ceremony and giant cake-cutting provided by Hy-Vee. Families will gather downtown to drop off their decorated pumpkins on the DeKalb County Courthouse lawn to enter into the Sycamore Lions Club’s contest.

This year’s theme is “Pumpkins in History” from Sycamore second grader Harrison Rowland. Retired Sycamore High School principal Tim Carlson was named Grand Marshal in the parade.

Thursday, Oct. 26, will feature downtown trick-or-treating, and Friday is the United Methodist Church’s Craft Show. The carnivals run Friday, Oct. 27, through Sunday, Oct. 29. Food vendors serve up fare throughout the weekend. Saturday, Oct. 28, features among other events Sycamore Rotary Club’s Pancake Breakfast, ACS/Cornerstone Campus’ Craft & Vendor Show and the Kiwanis Club’s pie-eating contest. Sunday’s festivities include the Sycamore Chamber of Commerce’s 10K Pumpkin Run and culminates in the Pumpkin Parade at 1 p.m.

Regnery said while it’s fun to put on a good party for families who attend, it’s equally important for participants to remember the festival also serves as a nonprofit fundraiser.

“The festival is a 501c3 charity, and part of our mission statement is to provide a venue for nonprofits to fundraise,” Regnery said. “So all of our vendors downtown during the festival are nonprofits. They make up the membership of our organization.”

That organization is always on the lookout for new nonprofit members, Regnery said. He said he’s expressly grateful to those who’ve made the festival what it is.

“The courthouse is one of the most beautiful buildings of DeKalb County. You can go look at the courthouse and on the courthouse lawn are hundreds of pumpkins all decorated by Sycamore residents who just want to show off their art,” Regnery said. “There’s just something really magical about doing it downtown.”

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