Evening Affairs    

When the stars come out during Derby Week, the real spectacle begins. The lights brighten, the music rises, and the night becomes a stage for the bold and the beautifully dressed. From red-carpet arrivals and private soirées to intimate dinners that linger past midnight, Charlene’s Evening Affairs ensure your entrance is refined, graceful and unforgettable. During Derby Season, it’s not just about where the party is — it’s about how you make your entrance.

Derby Week 2026
  Evening Affairs Availability:  

(Churchill Opening Night)

• Saturday, April 25th

Now Booking!

(Derby Week Kickoff)

• Monday, April 27th

Now Booking!

(502s-day Night)

• Tuesday, April 28th

Now Booking!

(Wins-day Night)

• Wednesday, April 29th

* Sold Out *

(Thurby Night)

• Thursday, April 30th

Now Booking!

• Saturday, May 2nd

(Oaks Night/Derby Eve)

• Friday, May 1st

Now Booking!

Now Booking!

(Kentucky Derby Night)

Book Evening Affairs

Refined Evenings.
Grand Arrivals.

Evening Affairs

Crowd of people at a the Silks Bash Gala, many with hands raised, smiling and enjoying the event, with lights and decorations in the background.
Four people on the purple carpet dressed in Derby best, smiling and standing close together in front of a backdrop with logos and text reading 'Silks Bash.'

When the evening calls for something extraordinary, Charlene’s Evening Affairs answer with timeless allure. Whether it’s a gala gleaming with champagne light, a private dinner tucked beneath crystal chandeliers, or a bespoke night designed entirely around you, The Colonel’s Reserve ensures every detail unfolds with ease and elegance. From your first toast to your final farewell, Charlene transforms the night into something more — an experience defined not by where you go, but how you get there and the impression that you make when you arrive!


What’s Included:

  • Up to six hours of private, on-call evening service, with your Kentucky Colonel chauffeur dedicated exclusively to your itinerary — from dinner reservations to private events and everything in between.

  • Seamless coordination and timing to ensure every arrival feels deliberate — your chauffeur handles all logistics so you can focus solely on the moment.

  • Complimentary itinerary planning assistance, whether for Derby Week galas, cocktail receptions, or custom evening requests.

  • Bottled water, discreet service, and music of your choice tailored to the evening’s mood.

  • No hidden fees or surcharges — only polished, uninterrupted service from start to finish.


Sample Itinerary — Cocktails & Dinner Experience

  • 6:00 PM – Chauffeur arrival and guest pick-up at hotel or residence

  • 6:30 PM – Cocktails at your chosen bar or lounge (reservations coordinated upon request)

  • 8:00 PM – Arriver to Dinner reservation at one of Louisville’s acclaimed restaurants

  • 10:00 PM – Optional nightcap or scenic post-dinner drive through the historic districts

  • 11:00 PM – Final drop-off at hotel or residence

The Ruby Room at Jeff Ruby's, Louisville, with red velvet curtains, red chairs, and white tablecloths set for dining. A chandelier hangs from the ceiling, and there is a large portrait of a man in formal attire on the wall.

Sample Itinerary — Evening Gala or Private Event

  • 6:00 PM – Chauffeur arrival and guest pick-up at hotel or residence

  • 6:30 PM – Optional pre-event cocktail stop at a preferred lounge or private club

  • 7:30 PM – Red-carpet or event arrival
    (drop-off at venue entrance; vehicle remains on call)

  • 9:30 PM – Chauffeur standing by for mid-event transfers
    or guest coordination as needed

  • 11:30 PM – Event departure and scenic return drive through the city lights

  • 12:00 AM – Final drop-off at hotel or after-party destination

The Ruby Room, Jeff Ruby’s Steakhouse - Louisville, KY

The Silks Bash Gala with many people dancing and socializing inside a brightly lit venue with red lighting and cowboy-themed decorations.

Silks Bash Derby Eve - Louisville, KY

Derby Week nights are Charlene’s most coveted evenings of the year and are extremely limited in availability! Each evening experience may be tailored upon request to reflect your vision, pace, and preferred destinations. Don’t delay - reserve your evening today!

To reserve your once-in-a-lifetime night with Charlene through The Colonel’s Reserve, just fill out the form below for a custom quote!

Make your Derby Week legendary!

Please note: due to the high demand of the season, it is the responsibility of guests to secure reservations and admission to ticketed events in advance. While The Colonel’s Reserve ensures your arrival is seamless, entry and seating cannot be guaranteed.

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!

Book The Colonel’s Reserve

Close-up of Charlene, a 1964 Cadillac Eldorado convertible, and her interior with white leather seats and a teal exterior, parked outdoors on a paved surface.