1950s
Keeneland began the 1950s with an updated box seating area for the Grandstand, replacing the original wooden structure of the section with concrete, steel, and aluminum. Starting in 1952, Keeneland established a rewards program for graded stakes races, the Milestone Trophy Program. Owners receive a gold julep cup for each stakes race won. Today, when owners reach 8 wins, they receive a gold tray; after 16 stakes wins, a pitcher; then a bowl, and finally, a vase, all of which are now designed by Tiffany & Co.
The Grandstand was enlarged in 1953 with an additional 1,542 seats and a new dining room. In the same year, the finish line was moved closer to the first turn, making the stretch run longer. A new training track was completed in 1955, and the main track surface was overhauled to improve drainage in 1956.