What I Learned From My First Kentucky Derby

There is no place like Churchill Downs. Cliché? Maybe. A lie? Far from it. The atmosphere, the fashion, and the people are unparalleled. My first Kentucky Derby experience was truly one of the most special weekends and it really is the greatest two minutes in sports. If the Derby is on your bucket list, I cannot encourage you enough to go!

I wanted to pass along a few lessons that I learned from attending this year to help you when you are considering going or planning your trip. Later, I will outline our itinerary and tell you a little bit more about our trip as well as detail where I got my outfit.

This is by no means an all intensive guide, rather just some takeaways from my first experience. Be sure to check out the official Kentucky Derby website for more details.

1. Test Drive Those Shoes

If you want to wear your pretty heels, absolutely wear them! They make the outfit! BUT, and hear us on this, do NOT wear them for the first time to the derby. Also, when selecting shoes, first keep in mind where you will be sitting in Churchill Downs. If you are in the infield, we recommend you opt for a flat or a wedge over a stiletto. You are going to be on your feet a lot. If you are in the grandstand for example, we recommend you look for a block heel or something that is going to have a good amount of support in it.

Now, you will be doing a lot of walking so this is not the time for your daintiest heels that barely stay on your feet. Look for something that is secure and will hold your foot in. Once you have your shoes, test drive them and break them in. This is so important. Don’t be like me and find out real quickly that your foot doesn’t stay in your shoes once you arrive at Churchill Downs and you left your back up heels in Nashville.

Finally, pack those flip flops and bring them! Or, bring some extra money for a pair from the gift shop. Race days are long days and you will be thanking your earlier self that packed the flips flops by the end of the day. We recommend you look for a pair that fold up to fit in your purse or bring a larger clear bag to throw them in. The happier your feet, the happier you will be.

2. Ubers, buses, and golf carts oh my!

We highly recommend that you look into finding a bus to take to Churchill Downs from your hotel or purchase parking. The ride share pick up and drop off place is a very long walk from the gates and there is no signage telling you where to go. This is why we highly recommend you take a bus down there or park and ride the bus to the gates. The bus we took was through Derby Experiences who we used to book our trip.

3. Un-expectations and Things to Remember

There were a few things that I was not expecting or was simply not aware of. First was that smoking cigars is a large part of the Derby experience and you can smoke anywhere. This is just something to consider which I personally was not aware of. Secondly, it was a nice surprise to find out the drinks are apart of your ticket but do not forget to tip!

A few things to remember:

  • Bring plenty of cash for betting and for tips
  • Bring a clear bag to carry the necessities (like your change of shoes)
  • Be prepared for the weather and bring ponchos in case it rains
  • Remember it is a marathon and not a sprint
Itinerary Details

Through Derby Experiences, we went on an excursion to Hermitage Farm for a tour of the farm to learn about their operations and see the horses. They had the cutest foals and we got to pet a few of their horses. Then we hopped back on the bus and headed to Danville for lunch then to Wilderness Trail Distillery for a tour and tasting. It was really interesting to see how their bourbon is made and how they store the barrels to age.

Friday, Oaks Day:

We began the day early in the morning with one of my favorite parts of the trip: Dawn at the Downs. We got to tour the stables at Churchill Downs and see the racehorses warm up. It was really cool to see the behind the scenes operations and we even got to spot last year’s Derby winner Rich Strike who was racing in another race this year. The view of the twin spires during sunrise was incredible. We ate breakfast as part of the experience on site and then headed back to the hotel for a quick nap before we got ready for the day.

Then, we caught the 11am bus to the racetrack and got a little lost before we found the grandstand. We tried our hand at betting and checked out the gift shop. I found my new favorite drink, the Lily, and we made friends with the other couple in our box. We got tickets to the Affirmed Lounge where we could go into the Derby Museum for good food, drinks and live music. If you are looking to elevate your experience I would highly suggest purchasing tickets to this lounge. We cheered the Oaks horses on and admired the gorgeous lily wreath they placed on the winner. Lastly, we attended the Fillies & Lillies fundraiser and I spied one of my favorite country music artists (shhh).

Saturday, Derby Day:

We caught the 11am bus again and took lots of photos on our way to our seats. The lines for betting were much longer on Derby day so be sure to account for that so that you don’t miss the races you want to see. We ate lunch in the Affirmed Lounge once again and enjoyed some mint juleps. Watching them move the starting gate around for each race was really interesting and we saw some of the coolest hats. Carly Pearce sounded incredible singing the national anthem and the walkover was so cool to see. We cheered so loud for the derby race and those two minutes were full of tension. It went dead silent before the horses came out of the gate and a few winners shed tears when Mage crossed the finish line.

Outfit Details

Fascinator: The Hat Doctor on Etsy

Dress: Altar’d State

Shoes: Steve Madden

As one of our tour guides said: you will feel like you got hit by a truck by the end but it is a glorious one. We had a blast and I highly encourage you to start planning your trip to the Kentucky Derby. Grab your fancy hat, your (supportive) shoes and cheer for your favorites.

If you have any questions please contact us and we will be happy to answer them!

Tell us about your own Derby experience.

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