Here’s the unofficial guide to the best and worst hats at the Kentucky Derby. Tomorrow, 20 of the world’s best three-year-olds will line up and race in the 144th Kentucky Derby. The $2 million Kentucky Derby is at Churchill Downs in Louisville, Kentucky. The Florida Derby has produced three of the last five Kentucky Derby winners: Orb, Nyquist and Always Dreaming. Audible, Hofburg and Promises Fullfilled are the three 2018 Florida Derby runners expected in this year’s Derby. Last year fans bet a whopping $209,179,920 on Kentucky Derby races.