The Kentucky Derby Experience: Part 1


Lifestyle, Travel / Tuesday, May 8th, 2018

And they’re off!

That’s what I was thinking as we boarding a plane on our way to Louisville for the 144th running of The Kentucky Derby. A little over a thousand miles and what felt like a thousand mint juleps later, I finally knew what it was like to behold those iconic twin spires and smell the wet dirt churned up by some of the greatest equine athletes and their jockeys. By the end of the weekend my head was buzzing with My Old Kentucky Home and I didn’t want to leave.

Do you watch The Kentucky Derby? We have always enjoyed seeing it on television and making mint juleps at home. Our little Derby party of two has been one of my favorite weekends of the year. But nothing can compare to the actual experience. Over 157,000 people attended this year on a record rainfall day. In spite of the dark and wet weather, the unique majesty of Churchill Downs shined through. From the colorful patterned silks to the larger-than-life hats, The Kentucky Derby experience is one that I’ll never forget.

I thought it best to split my original blog post into two parts because we spent two days at the track. This is part 1 and will cover The Kentucky Oaks race which is held the day before the Derby. Part 2 will be all about the main event so stay tuned!

Kentucky Derby Experience | What to Expect at the Kentucky Derby | Cathedrals and Cafes Blog

Kentucky Derby Experience | What to Expect at the Kentucky Derby | Cathedrals and Cafes Blog

Kentucky Derby Experience | What to Expect at the Kentucky Derby | Cathedrals and Cafes Blog

Kentucky Derby Experience | What to Expect at the Kentucky Derby | Kentucky Oaks | Cathedrals and Cafes Blog

Kentucky Derby Experience | What to Expect at the Kentucky Derby | Kentucky Oaks | Cathedrals and Cafes Blog

The Longines Kentucky Oaks is referred to as the “lilies for the fillies” as it is a race among 3-year old female horses and the winner receives a drape of lilies (as opposed to roses). The event raises awareness for breast and ovarian cancer and ends with a survivors’ parade along the track. Churchill Downs is draped in pink and attendees are encouraged to incorporate pink into their attire for an all-day “pink out.” The signature drink is the Oaks Lily and a portion of each sale goes to charity. You can find the official recipe here. It’s delicious!

I wore a gorgeous double-v neck dark blue midi dress patterned with pink flowers. A matching pink floral fascinator (found on Amazon) and nude heels completed the look. I did my best to “think pink” but found this style to be perfect. It even had pockets (which you know I love in a dress) which were perfect for keeping my money and bets. The heels were a comfortable height for walking and standing a good portion of the day.

Our seats were located in the Turf Club overlooking the finish line. You could not ask for a better view and being inside with inclement weather never hurts either. All food and beverages were included. The cheddar popcorn drizzled with chocolate was an afternoon snack favorite!

Keep your eyes out for celebrities at Churchill Downs! I managed to spot actor Blair Underwood but that was about it. Even still, the thought of maybe, just maybe, seeing someone famous was pretty exciting.

The real excitement, however, was down on the track. Races are held either on the turf or the dirt, both of which gets kicked up quite a bit. There’s nothing like hearing the bugler’s call to post followed by the crowd’s cheer, and before you even know it, they’re off!

Just a little tip: Cameras with detachable lenses are not allowed inside Churchill Downs. I shot everything for this post with iPhone.

Following the race we went to dinner at Bistro Le Relais, a locals-know-best French restaurant located in the airport terminal of historic Bowman Field. You can watch planes land, including many private jets, while dining in the art deco style building that dates to 1919. It’s gorgeous and the food is fantastic. You’ll be saying, “Here’s looking at you, kid,” over a perfectly mixed French 75. It’s also a nice spot for a few photos. Reservations are highly recommended.

What to Wear to the Kentucky Derby | Kentucky Derby Dresses | Cathedrals and Cafes Blog

What to Wear to the Kentucky Derby | Kentucky Derby Dresses | Cathedrals and Cafes Blog

What to Wear to the Kentucky Derby | Kentucky Derby Dresses | Cathedrals and Cafes Blog

Shop our Kentucky Oaks looks:


Our Kentucky Derby experience was made possible by our dear Louisville friends. To P. & J., and M. & S. – thank you so much for a weekend we will always cherish! You have made a special place in my heart for your home.

Xo – Erin

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