A Peek into the South Side Pie Challenge 2019

Author & Photographer: Erica Hogan

Grandparents and grandchildren, college students on a study break, south-siders of all ages, gathered around round tables, sharing slices of pie, at the Hyde Park Neighborhood Club for the eighth annual South Side Pie Challenge last Saturday. 

Every year, pie bakers from all neighborhoods of the South Side enter their pies in the South Side Pie Challenge. There are four categories of competition: fruit pies, nut pies, pumpkin/sweet potato pies and creme pies. Competitors may enter one pie per category, paying a registration fee for each. Dishes are judged by criteria that include crust, filling, flavor and overall taste. The judges are all people from Chicago’s culinary world, and have included figures such as Evan Robinson from Master Chef Junior, Paula Haney of the Hoosier Mama Pie Company, Kirsten Esterly, the general manager of the Medici restaurants, and Maya-Camille Broussard from Justice of the Pies. Three winners are chosen in each category, and are awarded cookbooks from 57th Street Books. 

Hyde Parkers Julie Vassilatos and Kate Agrawal launched the South Side Pie Challenge in 2012. Agrawal had just entered the Bucktown Apple Pie Contest in the North Side and had brought Vassilatos, a food blogger, along to the competition. They thought that the South Side should also have its own pie contest, and decided to start the South Side Pie Challenge to benefit the Hyde Park and Kenwood Hunger Program. 

For $4 a slice, spectators can have their pick of the many delicious, beautiful and creatively named pies on offer. This year, with all the turmoil in our political landscape, there were not one but two “im-peach-ment” pies offered in the fruit category. They were joined by a “Whistle-Bluer Quid Pro Pie.” Standouts on the decorative front included the “Autumn Yin Yang Pumpkin Pie,” which had a glossy yin-yang on the surface made of a berry filling and a pumpkin filling, the “Sassy Pear Pie,” a finalist in the fruit pie category that had a top crust made of cutouts of leaves, and the “Nut-thing Compares to This Pie,” a finalist in the nut category which had an outer rim made of delicately layered pastry leaves. 

While my stomach just couldn’t handle trying every pie on display, I got to try many of the competing pies with the help of some friends. Standouts include fourth-year Harini Shah’s Sweet Potato Pie, which was perfectly smooth and not too sweet, the “Dreamy Creamy Lemon Pie,” a finalist in the creme pie category, which had a fresh and tart lemon filling which contrasted beautifully with its crunchy and crumbly graham cracker crust, a s’more pie also in the creme category which managed to combine a chocolate filling and marshmallow topping without becoming cloyingly sweet, and a passionfruit creme pie which was a light and bright break from its competitors with heavier flavors, and a welcome reminder of warm weather a couple days after the first snow of the season. 

Another highlight of the event was the musicians playing for the crowd. They played a banjo and a zither, a string instrument popular in Appalachian folk and early country music. Occasionally, they brought out a jig doll, otherwise known as a limberjack man—a small, wooden doll that can be made to tap dance along to the music. The children in the crowd especially loved the musicians and danced along to their songs.

While the pies were delicious, my favorite part of the event was the sense of community it fostered. I saw it in the children, making new friends as they danced along to the banjo. I saw it in the families and friends enjoying slices of pie together. I saw it especially in the volunteers and pie bakers who came together to put together an event for the community, and to benefit the most vulnerable in the South Side.