Fall Festival & Chili Cook-Off

Get ready to welcome Fall with a day of festive fun, delicious flavors, and local shopping at the Downtown Street Market! Brooksville Main Street is excited to host a special edition of the market featuring a Fall Festival and Chili Cook-Off, bringing the community together for a celebration of all things fall.

Join us on Saturday, October 18th, from 10:00 AM to 2:00 PM as S Brooksville Ave transforms into a lively marketplace filled with seasonal décor, handmade crafts, and specialty food vendors. Visitors can explore a variety of fall-themed treats, shop unique artisan goods, and enjoy festive activities for the whole family!

Chili Cook-Off Showdown! One of this month’s market highlights will be a fun Chili Cook-Off where local chefs and home cooks will compete for the title of Best Chili in Brooksville!

Attendees can sample a variety of chili recipes and vote for their favorite while enjoying entertainment and the warm, welcoming atmosphere of historic downtown.

Guests can also enjoy music, kids' activities, and festive photo opportunities, making it a can’t-miss event for all ages.

The Downtown Street Market is a family-friendly and pet-friendly event, so bring your loved ones—both two-legged and four-legged—for a day of fun and festivities.