The Iron Horse Hotel, presents DOWN AND DERBY 2026—Milwaukee’s largest Kentucky Derby event! Bringing southern charm with a midwestern twist, this celebration kicks off at 12 PM. Watch the preshow and races on the jumbotron while enjoying live music, fantastic food trucks, local vendors, curated cigars by Shaker’s Cigar Bar, and, of course, Derby-themed beverages from the bar.
Admission is free, but VIP tickets are available for those looking for a more thoroughbred experience, which includes a private terrace, drink tickets, and a more refined food offering – think oysters!
Dress in your Derby best to win prizes, pick your horse, and get ready for a day of excitement, elegance, and southern hospitality—Milwaukee style! Don’t miss out on the biggest Derby celebration in the city.
