A Weekend at Churchill Downs

The hats were big. The bourbon was flowing. And for one unforgettable long weekend, Members experienced the Kentucky Derby in true Club style. From private dinners on storied horse farms to milliner-led headwear sessions and suite-level views at Churchill Downs, the itinerary blended Southern hospitality with bucket-list moments. What followed was a whirlwind of mint juleps, race-day glamour, and inside access to one of the most iconic sporting events in the world.

Thursday, May 1: Arrival

After arriving in Louisville, Members checked into the Brown Hotel — a Roaring Twenties landmark known for its old-school glamour (and its equally famous hot brown sandwich). The group’s first outing: Hermitage Farm, a scenic working stud farm just outside the city. After a short tour and Q&A with the barn owner on all things breeding and bloodlines, Members sat down to a three-course, farm-to-table dinner made with ingredients grown right on-site. The evening wrapped with a classic cocktail experience: a mint julep-making session that ensured everyone had their signature sip perfected ahead of race day.

Friday, May 2: Oaks Day

Oaks Day, the traditional prelude to the Derby, turned into a festive flurry of feathers, flowers, and shades of pink. Members began the day in a private suite with a Kentucky Derby-featured milliner, creating custom headwear over mimosas and pastries. Then it was off to Churchill Downs, where our private Starting Gate Suite offered sweeping views, bottomless cocktails, and front-row access to the action. The day’s highlight? Watching Good Cheer take the Kentucky Oaks — an elite race for three-year-old fillies — while Members cheered in full ‘Pink Out’ spirit in support of breast cancer awareness.

Saturday, May 3: Derby Day

This was the day to dress up and lean in. After a relaxed morning, Members suited up for the main event, returning to our private suite at Churchill Downs for another round of food, champagne, and thrilling finishes.

Surprises included a visit from Kentucky Governor Andy Beshear and a one-on-one session with horse racing expert Ellis Star, who shared insider tips and Derby lore between races. (Yes, he’s the guy who placed in the top five percent at the National Horseplayers Championship. No big deal.) There were personal wins too — the Sinor family’s horse ran strong in Race 11, and the Cullums made it onto the field for Race 14 thanks to a friend’s big win.

And finally: the Derby itself. After Simone Biles gave the “riders up” call and the marching band played “My Old Kentucky Home,” 19 horses charged onto the rain-soaked track. Sovereignty took the crown in front of 147,000 roaring fans, including ours.

Sunday, May 4: Departure

The weekend wrapped with smooth check-outs, private transfers, and a few extra hours of sleep. As Members departed Louisville — hats in hand, betting slips in pockets — they left not only with unforgettable memories, but also with a deeper appreciation for the tradition, pageantry, and thrill that make the Kentucky Derby a true American classic.