Kentucky Derby Festival and Courtesy Cadillac are giving Festival fans a chance to win a new Cadillac during this year’s Festival!

To help promote the Courtesy Cadillac Festival Challenge, a 2026 Cadillac CT4 Luxury Sedan was wrapped in the Festival’s signature pink and teal Pegasus pattern.

To enter, fans (18 and over) complete an online registration between March 23 and Saturday, May 2, 2026. The contest is limited to one entry per name, email and phone number.

Fans can get a closer look at the Pegasus Cadillac at upcoming Festival events including:

• Dillard’s Spring Fashion Show (March 26)
• Fillies Derby Ball Presented by Courtesy Cadillac (March 28)
• Republic Bank BourbonVille (April 2)
• Caesars Foundation of Floyd County FamFest (April 3)
• Block Party Presented by Humana and Park Community Credit Union (April 4)
• Thunder Over Louisville Presented by Caesars Southern Indiana, Ford Motor Company, LG&E, Meijer, UA Local 502 and UPS – (April 18)
• L&N Federal Credit Union Great BalloonFest (April 23-25)
• Zoeller Pump Company Pegasus Parade (April 26)
• Commonwealth Credit Union WineFest (April 28)
• Shepherd Insurance Great Steamboat Race (April 29)

To enter, fans (18 and over) complete an online registration between March 23 and Saturday, May 2, 2026.

600 of those registrants will be randomly selected to participate in a Lucky List Contest, where they will try to put eight (8) items in a specific order. The first entrant to correctly submit the winning list will win a 2026 Cadillac CT4 Luxury Sedan, in its original finish, valued at $40,000.If the items are listed correctly, a winner will be announced on or about Wednesday, May 6, 2026. There is no guarantee there will be a winner.

The contest is limited to one entry per name, email and phone number.

CLICK HERE for Official Rules.