Saturday, January 31st from 11 AM to 3 PM
Winter might be chilly, but downtown Oconomowoc is about to get red-hot! The 17th Annual Oconomowoc Chili Fest is happening on Saturday, January 31, 2026, from 11 AM to 3 PM in the heart of downtown, and you’re invited to be part of the fun.
What’s Chili Fest All About?
Chili Fest is a beloved winter tradition that brings together local businesses to showcase their best chili recipes, signature dishes, and creative Bloody Mary drinks. Attendees can stroll Wisconsin Avenue and Main Street while enjoying an exciting variety of bold flavors — up to 25 tasting opportunities throughout downtown.
Whether you’re a die-hard chili fan or just looking for a fun way to spend a winter Saturday, Chili Fest fills the streets with warmth, flavor, and community spirit.
Supporting Local Businesses
One of the best parts of Chili Fest is seeing how our community businesses get involved. Here is the list of local favorites who are joining the fun!
Bella Gusto Italian Deli & Pizzeria
Cornerstone Sports Pub & Eatery
Fiesta Cancun Mexican Restaurant & Bar
North 48 Lake Country / Hilton Garden Inn Oconomowoc at Pabst Farms
Sherper’s / The Chocolate Factory – Oconomowoc
Sweet P’s Pantry Artisan Toffee and Chocolates
Thirsty Bird Saloon /Lake Country DockHounds
Tickets are sold out, but there is still plenty to do!
Though Chili Fest tickets have officially sold out this year, that doesn’t mean you should miss out on the excitement downtown! This vibrant area is alive with friendly energy, delicious food, and great places to explore.
Here’s how to make the most of your Chili Fest day downtown:
- Dine at local restaurants — grab lunch or a warming beverage before or after the event.
- Browse downtown shops — unique boutiques and gift shops are ready to welcome you.
- Catch up with friends — stop in a relaxing winter hangout grab a drink at a local coffee shop or bar.
- Enjoy the ambiance — Downtown Oconomowoc is buzzing during Chili Fest, even for those without tasting wristbands.
This year’s Chili Fest celebrates not just great food, but the community spirit and support of local businesses that make Oconomowoc special.
We’re so grateful for the amazing businesses that participate, and we can’t wait to see friends, families, and neighbors downtown enjoying everything Chili Fest has to offer. Come for the energy, stay for the food and local flavor. There’s plenty to enjoy and explore!
Let’s make this Chili Fest one to remember!
