About the Festival of Racing
What to EXPECT
The Inaugural Oak Grove Festival of Racing kicks off on Monday, May 4, 2026. This premier two-week celebration features five days of elite racing with an estimated $2,750,000 in total purses, culminating in a blockbuster $1.5 million program on Saturday, May 16.
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+ 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.
Derby Day: The $1.5 Million Main Event
The festival reaches its pinnacle on May 16 with a card headlined by two major new stakes:
- $500,000 Oak Grove Trotting Derby (3-year-old male trotters)
- $300,000 Oak Grove Trotting Oaks (3-year-old fillies)
In addition to live action, fans can wager on the Preakness Stakes and live racing from Churchill Downs throughout the day.
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.
What to Wear
Hotels
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Oak Grove Derby Day
The Racing Day
Oak Grove Derby Day Race Card (11 Races)
1. Oak Grove Derby Day Race Card (11 Races)
2 Bronze Consolation Races $50,000 each
4-Year-Old Series 1 Finals (4 Races @ $100,000 each)
Oak Grove Trotting Derby Silver Consolation Race: $75,000
Oak Grove Trotting Oaks Silver Consolation Race: $75,000
Oak Grove Trotting Mare Invitational: $100,000 or Other Race
Oak Grove Trotting Oaks: $300,000
Oak Grove Trotting Derby: $500,000
VIP Experience
Food & Drinks
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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
