Kentucky Roses unfolds across two timelines - present day and 1932 - at Churchill Downs. In present-day, Sadie Moore (Annable) works in the Churchill Downs greenhouse, dreaming of becoming a florist and one day contributing to the Derby's garland of roses, just like her great-grandmother, Gloria (Ledford). As Derby Day approaches, Sadie meets Ash Taylor (Walker), the son of Churchill Downs' CEO (Henry), who's been asked to do an emergency repair on the iconic Twin Spires after a storm left one damaged. Both Sadie and Ash feel the weight of family legacy and the desire to carve out their own paths. Sparks fly, and their budding romance is complicated by a long-buried connection between their families - a bittersweet love story from the past that threatens to repeat itself.