LAST CHANCE to win 4 FREE tickets (over $500 in value) to The Kentucky Bourby on Saturday! Grab a couple friends and enjoy bourbon tastings, live entertainment, food from local chefs and a silent auction, all in support of an incredible cause.

The event is hosted by TKO Flight Club, a nonprofit committed to improving the lives of those affected by Parkinson’s. Your participation helps fund impactful initiatives, including therapy programs, support groups, and ongoing research efforts.

PS - Everyone who enters will get an exclusive 502 Weekender code for 25% off, so you can still check it out even if you don’t win.

Saturday 11:30am

Get ready for Derby week the best way possible with Opening Day at Churchill Downs, featuring the Oaks and Kentucky Derby post-position draws. KDF Marathon and Mini Marathon finishers receive free admission with their medal.

Sunday 3pm

The Pegasus Parade returns Sunday with a 17-block march down Broadway featuring bands, floats, and equestrian performances. An infamous Derby Festival tradition since 1956, it remains one of the city’s most recognizable spring events. Locals can enjoy free bleacher seating or pay for VIP viewing along the route.

Wednesday 5-10pm

Waterfront Wednesday kicks off its 2026 season this week at Waterfront Park, featuring Deep Blue Something and Small Time Napoleon. The updated format includes earlier 90-minute headliner sets and expanded local artist performances. The free event opens at 5pm with music starting at 6:30pm.

Great Balloon Glow - Thurs & Fri 9pm
Rush-Hour Race - Friday 7am
Great Balloon Race - Saturday 7am

Across three days, the Great BalloonFest brings Balloon Glow nights to Waterfront Park and early morning races to Bowman Field. Each event offers a unique experience, from close-up views on the ground to full flights overhead. It’s a signature Derby Festival tradition that brings locals together each year. Keep an eye out for Jeffie, the 10-foot inflatable dog popping up at KDF events, where you can snap a photo and enter to win prizes from Jefferson Animal Hospital!

Sat & Sun 10am-6pm

More than 200 artists are gathering for the Cherokee Triangle Art Fair, a free two-day event set in the historic Cherokee Triangle neighborhood. The event includes art, food, live entertainment, and a kickoff Children’s Parade, plus a Saturday evening street party. Proceeds from the volunteer-run event support local community initiatives.

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