Kentucky Oaks Day
On the eve of the Derby, the Kentucky Oaks takes center stage — a day devoted to beauty, grace, and the power of tradition. Awash in shades of pink, it honors the stargazer lily and celebrates the spirit of women with unmistakable Southern charm. Experience the elegance and pageantry of the Oaks in lasting style with Charlene and The Colonel’s Reserve—an experience designed to be remembered long after the final toast.
The 152nd Running of the Kentucky Oaks
Friday, May 1, 2026
Now Booking!
A Celebration Steeped in Tradition & Meaning
Kentucky Oaks Day
The day before the Derby, the Bluegrass blooms in pink and white as Kentucky celebrates its most elegant tradition — the Kentucky Oaks. It’s a gentler pageant, but no less grand. With over a decade of Derby Week experience, The Colonel’s Reserve ensures your journey to Churchill Downs unfolds in unhurried style — refined, radiant, and worthy of the flowing lilies themselves. From your first step onto Central Avenue to your grand arrival beneath the Twin Spires, every detail is handled with poise and polish — so you can arrive in style to see, and to be seen.
What’s Included:
Minimum of 10 hours of active and on-call service each day with a fully attentive Kentucky Colonel as your chauffeur — ready to take you wherever you need to be, whenever you wish.
Premium parking at Churchill Downs, arranged in advance, ensuring Charlene is always ready and waiting.
No extra charges. No hidden fees. Everything is included — every moment, accounted for.
Sample Itinerary — Kentucky Oaks Day:
10:00 AM – Pick-up at your hotel
10:30 AM – Brunch reservation at your chosen restaurant
12:00 PM – Drop-off at Churchill Downs (locations vary — from on-property to surrounding area lots)
7:00 PM – Depart Churchill Downs
7:30 PM – Final drop off at hotel
- OR -
Return to hotel to refresh and prepare for dinner (optional)8:00 PM – Dinner reservation / gala event / private party (optional)
10:00 PM – Final drop-off at your hotel
Kentucky Derby and Kentucky Oaks days are Charlene’s most coveted days of the year and are extremely limited in availability!
To reserve your once-in-a-lifetime day with Charlene through The Colonel’s Reserve, just fill out the form below for a custom quote!
Make your Kentucky Oaks experience legendary!
Book The Colonel’s Reserve
Interested in booking this once-in-a-lifetime Reserve experience with Charlene? Don’t wait! Fill out the required info and we will be in touch shortly. We can’t wait to welcome you!
