South Side Pie Challenge

Past entrants into the South Side Pie Challenge undergo sampling. 

Though it was rumored to have ended, the South Side Pie Challenge will return to the Hyde Park Neighborhood Club on Sunday, Nov. 6 from 2 p.m. to 5 p.m.

The 11-year-old tradition of dozens of amateur bakers testing their pie-baking prowess against their neighbors continues with new leadership at the helm, after pie challenge co-founder Julie Vassilatos hung up her apron last year.

"I wouldn't say that we're reinventing the wheel," said Molly Herron, one of this year's challenge organizers. "Julie did an amazing job creating the pie challenge and we're doing out best to keep up with her and also bring it into its next decade."

In keeping with years past, the format is a juried contest across four categories — fruit, nut, cream and sweet potato/pumpkin — with funds going to the Hyde Park-Kenwood Hunger Programs. The event will take place inside the Neighborhood Club, 5480 S. Kenwood Ave.

New this year, the jury consists of a panel of pastry chefs from across the South Side, so as to pay respect to an endangered vocation.

"The pastry chef is going the way of the dodo (bird)... A lot of restaurants after the pandemic have phased out having a pastry department," said Herron. "We wanted to pull the pastry chef forward... So all these pies that are made by people in the community are being judged by the professionals, and we're respecting their profession."

(Pastry chefs across the country report difficulty finding jobs in restaurants and feeling pushed out of the industry, as much of their craft has been outsourced to companies mass producing sweets or to other lower-waged kitchen workers.)

Local flavor includes Mary Mastricola of La Petite Folie, 1504 E. 55th St., Kirsten Esterly —  a longtime judge and former general manager at Medici 1327 E. 57th St. —  and Stephanie Hart of the Greater Grand Crossing-based Brown Sugar Bakery, 328 E 75th St.

The event will also be accompanied by local children's music and dance groups, such as the South Side Suzuki Cooperative, the Hyde Park School of Dance and the Hyde Park Youth Symphony.

More than two years into the pandemic and in a time of rising inflation, Herron added that the need for area hunger programs has grown.

This time last year, the Hyde Park-Kenwood Hunger Programs were providing fresh produce, meats, dry and canned goods to about 45 to 50 households per week; this year, it's about 60 to 70 households.

"That's a pretty serious increase, particularly with inflation," said Herron. "People have lost jobs, they've dealt with sickness, and now things are also significantly more expensive."

In the last 10 years the challenge has raised more than $27,000. Part of these funds come from registration fees and pie-slice tickets; bakers pay $30 per pie (registration has closed) and attendees pay $4 per slice.

Last year, with eager attendees in lines throughout the day wrapping around Nichols Park, the competition fundraised more than $5,000. The 49 homemade pies entered into the challenge sold out quickly, and organizers had to make emergency trips to nearby bakeries to restock.

As of Friday, Oct. 28, this year's competition organizers had more than 40 pies in the reserves and a backup plan in place should they sell out again.

"It's for an incredibly important cause, it's really really fun and you're doing a good thing when you come and eat a slice of pie," concluded Herron.

Tickets for pie slices can be purchased at the challenge in cash. For more information visit

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