Escape to “A Caribbean Night at the Races” at Churchill Downs, where the thrill of live horse racing meets the vibrant spirit of the islands. Sway to the rhythm, soak in the tropical vibes, and let the summer breeze carry you away!

Saturday June 21 | Gates Open 5 p.m. | First Race 6 p.m.

Event Details:

What to Wear: For Caribbean Night at the Races, we’re inviting guests to dress the part with bright colors, breezy fabrics, and bold accessories. Think flowy dresses, fun prints, and statement pieces that capture the spirit of the islands—elevated with Derby flair. Vibrant. Stylish. Unforgettable.

Stage Lineup:

5:00pm Ben Bernhard is bringing the island vibes with all your favorite Jimmy Buffett hits — the perfect soundtrack to kick off our beachy bash!
8:00pm DJ Brandon Lee: From sand to stage, DJ Brandon Lee is bringing the coastal country soundtrack — think Kenny Chesney, Zac Brown Band, and all the feel-good summer jams, perfect for a laid-back night under the stars!

Event Highlights:

See Twiggy the Water-Skiing Squirrel: Watch the famous waterskiing squirrel, Twiggy, perform in three exciting shows throughout the evening. Watch in awe as Twiggy zooms across the water on her tiny skis, performing impressive tricks and stunts. (Time: TBD)
Dance Lessons with Cari’Fete Afro-Caribbean Dance Movement: Learn how to move with the rhythm of the islands! Cari’Fete will guide you through Belizean and Afro-Caribbean-inspired dance steps to get you ready to dance the night away. No experience needed—just bring your energy and island spirit! (Time: TBD/Location: TBD)
Airbrush Station by Bluegrass Airbrush: You asked, we listened! Our Airbrush Station is back and better than ever—grab a Caribbean inspired design and show off your Caribbean Night style with bold colors and tropical flair. First come, first served… don’t miss out!
Sunset Send–off: Cap off the night in unforgettable island style with our Sunset Send-Off! Gather around for a mesmerizing performance featuring fire dancers, stilt walkers and hula hoop artists—blending heat, rhythm, and movement as the sun sets on Caribbean Night at the Races.
Catch our roaming photo booth: strike a pose for your Postcard from Paradise! Smile big… you’re on island time!
“Beachside” Limbo Contest: Show off your flexibility island-style! Whether you’re in it to win it or just for fun, this tropical crowd favorite is sure to bring big laughs and even bigger energy.

Big Board Highlights:

Test your knowledge with Caribbean Trivia on the big board! From legendary music and vibrant festivals to island culture and iconic moments, show off your expertise and celebrate the spirit of the Caribbean. Don’t miss your chance to join the fun and see how well you really know the islands that bring the vibes!

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