Garvin Gate Blues Festival (Oct. 7–8)
Oak Street and Garvin Place
Free | Times vary
What began as a jam session in a parking lot is now “one of the most prestigious blues festivals between Chicago and Mississippi.” Set in Old Louisville, with the largest collection of Victorian homes in the nation, this two-day arts-and-music festival has two stages of continuous music from local and national acts, as well as food and drink from over 50 vendors.
Louisville City FC USL Cup Playoffs
Louisville Slugger Field
$5-$40 | 7 p.m.
Louisville City FC is continuing its march towards the USL Cup championship game, and the next opponent standing in its way is Charleston Battery. The win won’t come easily, so go support Louisville’s favorite pro team as it battles its way through this Eastern Conference Semifinal.
Free | 2 p.m.
Oktoberfest may be over is Deutschland, but it’s just getting started over here in Louisville land. Join Flat12 Bierwerks in Jeffersonville, Indiana for an Oktoberfest Party featuring beer stein races, giant beer pong, keg checkers, brats and the release of a new brew, Dunkelprinz or “dark prince.”
Insane Inflatable 5K
E.P. “Tom” Sawyer State Park
8:30 a.m. | $65-$100
Admit it, when you see kids at a party jumping around in the bouncy house, you secretly get very jealous. We all do, which is why the Insane Inflatable 5K was created. It’s a 3.1 mile long inflatable obstacle course with over 12 oversized inflatables and slides for adults. (Some say it’s even more fun than the bouncy house, but we can’t confirm that.)
Clifton’s Great Chili Cook Off
Frankfort Avenue & Pope Street
$10 | 1 p.m.
Although the weather may be a bit warmer than usual, that shouldn’t stop you from enjoying some piping-hot (and delicious) chili at this year’s Great Chili Cook Off. The best restaurants from around Louisville will descend upon the Clifton neighborhood with some heaping samples of their take on this fall/winter staple. Come with an empty belly and a big spoon.