Racing Calendar Highlights
- Monday, April 27: Derby and Oaks Prep races.
- Monday, May 4: Festival kickoff featuring Derby and Oaks eliminations and Kentucky Sire Stakes for 4-year-olds ($500,000+ est. in purses).
- Tuesday, May 5: Live Racing.
- Sunday, May 10: Mother’s Day program featuring the Annual Charity Corgi Dog Races.
- Monday, May 11: Live Racing.
- Saturday, May 16: DERBY DAY. Post time is 12:45 p.m. CDT.
Championship Stakes!
Elite Contenders!
Unmatched Purses!
Key Highlights
- Feature Events: $500K Trotting Derby & $300K Trotting Oaks headline the festival.
- Road to the Races: Win and you're in" races reward exceptional two-year-old performers with an automatic bid to the eliminations.
- Race Day Spotlight: Eliminations May 4 → Finals May 16 with $1.5M+ on the card.
At the heart of the Festival are the $500,000 Oak Grove Trotting Derby and $300,000 Trotting Oaks, showcasing the sport’s top three-year-old trotting talent. The “Road to” series rewards elite two-year-old performers with automatic entry, building a deep, competitive field. Action begins with elimination races on May 4 and culminates in a championship final on May 16, 2026.
Entertainment & VIP Experience
While general admission is free for the day of racing, fans can upgrade to an elevated VIP Experience. This includes private seating, homestretch dining with premium food, and a VIP ticket to the Jake Owen concert at the Moonshine Amphitheater.
Fill out the form below to request VIP tickets
Jake Owen
Saturday, May 16th • 8PM
Jake Owen is a country music mainstay with a career boasting a collection of gold and platinum records, 10 No.1 singles, and more than 2.5 Billion U.S. on-demand streams. The chart-topping superstar and ACM award winner is signatured by his laid-back style and hit recordings such as Barefoot Blue Jean Night. An exciting stop on his Dreams to Dream Tour!
Doors open at 7:00 • Show begins at 8:00
What to Wear
Style Inspiration
- Your “Derby Best:” Think polished, race-day elegance meets a relaxed, approachable charm.
- FOR THE LADIES
- Springtime Vibrance: Bright spring dresses, playful florals, or soft pastels.
- Go Big or Go Bold: Iconic hats or intricate fascinators. If it’s eye-catching, it’s perfect.
- The Finishing Touch: Accessories to make the look yours!
- FOR THE GENTLEMEN
- Southern Sophistication: Linen suits, light sport coats, or a crisp, well-fitted button-down are all winning bets.
- Show Your Personality: Don’t be afraid to lean into the tradition. Colorful tie, fun pocket square, just add your personality.
- EVERYONE: Comfortable shoes -- you’ll want to stroll, celebrate, and stay awhile
Dressing up -- it’s part of the fun. Take a cue from Derby Day style and lean into color, personality, and a little flair. Whether it’s a standout hat, a sharp jacket, or just a step above your everyday look, the Festival is your excuse to elevate. Come ready to turn heads, you’ll be part of the energy.
