For starters, September means the return of the annual Kentucky Bourbon Festival to Bardstown from the 12th to the 16th. Each of those six days is loaded with bourbon tastings, mixology classes, art displays, car shows, and/or food vendors, which works out to like, 746 things to do in total. The events are a mix of ticketed and free, and there is a designated Family Fun Area with train rides to distract the children while you enjoy your jazz and cigars. Then, less than an hour away, from September 22-23 you have Louisville’s Bourbon & Beyond, a bourbon, music, and food festival headlined this year by John Mayer, Lenny Kravitz, Robert Plant, and Sting. And despite the theme, it’s open to anyone aged 5 and up.