Oshkosh’s Chili Cook-Off


Ready to spice up your Saturday? Head over to the Chili Cook-Off on September 21st from 11am-4pm for the annual event that has everyone’s mouth watering. Contestants from world-class chefs, to BBQ dads, and chili fanatics all come together at the Leach Amphitheater to see who can stir up the best bowl. 



Interested in competing? Does your chili often illicit the “mmmmhhhhmm” noise paired with a couple of head nods and licked-clean bowl? You may have what it takes to be the next Chili Champion. Here’s the basic layout of the rules:

  • $25 cost of entry. All proceeds will benefit the Day by Day Warming Shelter, whose mission is “to provide safe, temporary shelter, food, and supportive services for adults.”
  • Teams can have a max of 4 members. That means you can pick 3 of your closest friends and family that you are willing to share your super secret batch recipe with. 
  • Chili must be ready by noon. You have all morning to chop, stir, fry, and simmer your chili, but no pre-preparation allowed. 
  • Multiple Cash Prizes. Rank on the top three for traditional chilli, specialty chili, or team spirit, and your team could be walking away with cold hard cash and bragging rights for an entire year. 
  • Chili Supplies Discount at the Piggly Wiggly. Stock up on your chili supplies at the Oshkosh Piggly Wiggly and receive a $20 discount if you spend $100 or more.



Maybe you don’t know how to cook chili, but you know a good cup when you taste one. Head on down to the Leach Amphitheater with an appetite and prepare to be blown away. Taste recipes made by home cooks from all around Wisconsin, and sample some local restaurant’s take on the classic dish. This could be the best lunch you have all year!

  • Doors open at 11, tastings start at noon. Wander around, talk to the chili chefs about their process and make some friends. Now is a great time to buy your tasting cups.
  • Tasting cups cost 50 cents each. Buy one, ten, twenty, or a hundred! All of the proceeds go directly to Day by Day Warming Shelter.
  • Vote for your favorite chef. Make your rounds and taste the different recipes. Find your favorite one and cast your vote. 
  • Winners are announced at 2. Stick around and see if your favorite chili won the big prize. 


Whether you are planning on cooking, sampling, or spectating, this great family-friendly event is the perfect intro to fall. As the days get shorter and the temperature starts to drop, chili season starts and we just can’t wait! 


Planning a trip of Oshkosh, WI this fall? Book a stay at the lovely Brayton Bed & Breakfast, where modern luxury meets historic style.