The Grandstand concerts are usually a mix of country stars and cover bands that think they know every word. For 2026, whispers say a 90s tribute band called “Smells Like Teen Spandex” might headline. I’m crossing my fingers for a full-on flannel shirt revival in the crowd.
There’s also a pie-eating contest where things get aggressive. Last year, a nine-year-old girl won by a full pie-length. She didn’t even look proud; she looked like a syrup-covered deity. I’m scared, but also inspired.
Weird & Wonderful: The Little Things
My favorite part of any fair is the oddball stuff. The Sheboygan County Fair 2026 has a “World’s Largest Cheese Curd” weigh-off and a knitting competition where the winning scarf looks like a llama in distress. You can also enter a “Best Beard” contest—even if your beard is just glued-on cotton balls.
And let’s not forget the exhibit hall. You’ll find prizewinning pickles, a quilt that probably took 300 hours, and a display of pinewood derby cars that look suspiciously like spaceships. It’s gloriously wholesome.
Sheboygan County Fair gets ready for Thursday opening
