This is an obvious must-see. Bourbon lover or not, Buffalo Trace Distillery is a beautiful place to visit, especially during October when the leaves begin to change. Schedule a free tour, or just stop by to graze the historical grounds & taste the World's most award winning bourbon.
Keeneland Racetrack is an iconic fall festivity in Kentucky during the month of October. The 2026 Fall Meet is scheduled to run from Friday, October 2, through Saturday, October 24 with the exception of Mondays & Tuesdays. Tickets sell out rather quickly, so be sure to sign up for the official Keeneland email list on their website for direct notifications regarding public ticket sale dates.