What it’s like to go to the Kentucky Derby and Kentucky Oaks at Churchill Downs.
I’ve always wanted to go to the Kentucky Derby, but I was never sure if I’d get the chance. Well … I got the chance!
Last weekend, Dave and I flew to Louisville for the 151st Kentucky Derby (as well as the Kentucky Oaks), and it was amazing. Even though I had watched the Derby on TV for years and had been to a couple Derby parties, I didn’t really know what to expect from this experience. While I was fully immersed in the moment during my time there, I knew right away it would be something worth writing about.
Today, I’m going to cover the racing, the outfits, the food, the facilities and what you should know before you go.
I’m sure you’re wondering, how and why did I get to go anyhow? Well, the long story short is this: Dave got an invite through his work in sports just a few weeks before the Derby. Once he found out he could bring a guest, we put the wheels in motion to get everything covered with Brady and my work, and then we went to Louisville and attended the events with two of his coworkers.
The cool thing about this being a work trip for Dave where we were hosted is that we didn’t have to pay for a ton (outside of my flight and souvenirs, etc.), which can’t be beat. Attending the Kentucky Derby is an expensive endeavor, and we’re so grateful that we were able to do it with a pretty minimal investment. It’s truly a big deal and one we don’t take lightly.
Now, let’s get into it …
The Kentucky Derby and the Kentucky Oaks are some major to-dos. And the Kentucky Derby is considered America’s oldest consecutive-running sporting event, which makes it extra special to be a part of. Going to the Kentucky Derby is a “bucket-list” activity for many, and it definitely was for us.
Here’s how it all went down …
We flew out of Charlotte on a Thursday night, and it seemed like more than half the people on our flight had hat bags or garment bags, so I could assume they were planning on attending the Derby too. Upon arrival, we found that the Louisville airport was not too big, and it was easy to get around, with very orderly ride-share pick-up and drop-off spots, as well as beautiful bouquets of fresh red-Derby roses lining the walkways.
While our travel was fairly uneventful, my round-trip flight was pricey (and of course, that was the one thing we had to pay for). We didn’t book very far in advance for this trip, and if you ever plan to attend the Derby, I suggest locking down your flight, hotel and dinner reservations months out, because things really fill up. And it sounds like a lot of people plan many months (if not a full year) ahead of time.
We stayed in downtown Louisville at a not-that-great hotel, but once again, it was not cheap and all that had been available. The good news is that we didn’t spend hardly any time at our hotel, so it wasn’t a big deal. We went out to dinner both Friday and Saturday night in Louisville and found places bustling with Derby attendees, some still in their attire from the day and some who had transitioned to regular clothes.
Now, on to the main events worth talking about …
The horse racing at the Kentucky Oaks and Kentucky Derby
The Kentucky Oaks and the Kentucky Derby are thoroughbred horse-racing events, which take place on the first Friday and the first Saturday in May, every single year.
Many people attend these events because they want to watch and bet on some of the best horses in the world. A fact I didn’t know until I attended is that there are around 10 races on Friday, the day of the Kentucky Oaks, and there are around 12 races on Saturday, the day of the Kentucky Derby. So it’s not just one race per day, it’s multiple.
(Here are my sunglasses.)
To be honest, I’m not that into horse racing, I’m not that into horses, and I never bet on sports either. Yet, I will say that watching the horses race was actually really thrilling. We had two different viewing spots, and it was cool to see the racing from above and even cooler to see it up close. Horses are such beautiful and powerful animals, and the way they give it their all is really awesome to see. (But I don’t like when the jockeys whack them — just saying — although I’ve heard this isn’t a big thing for the horses.)
I didn’t expect Dave and I would bet on any races, but once we were there, we ended up doing some wagering.
In fact, on our first time betting, we selected the first, second and third place horse correctly for a race on Kentucky Oaks day, thanks to some help from nearby betters. We would’ve won a good amount from that race, but we had a little issue with our betting ticket (it ended up in the garbage, by a mistake), so we weren’t able to cash in on that race (with a few laughs, of course).
We bet a few more times on day one and on day two and probably ended up losing a little overall — but not much. I must say that the feeling of watching the horse you chose run from behind and win is truly a rush. While I liked this part more than I had thought, it still wasn’t my favorite part. That’s coming …
By the way, Dave and I felt like we somewhat knew what was going on during the races, because we watched Netflix’s “Race for the Crown” series right before attending the Derby. It’s all about trainers, jockeys and owners and how much it takes to get a racehorse into an event like this, and it’s worth a watch if you’re into that type of thing. But if you really want to prep for watching racing and betting, you should learn how to read the little details in the programs.
Now, from the racing to the venue …
Visiting historic Churchill Downs in Louisville
The Kentucky Oaks and the Kentucky Derby both take place at a venue called Churchill Downs, and some call this the world’s most legendary racetrack.
Churchill Downs is about 15 minutes from downtown Louisville, and it’s situated in a neighborhood area. It’s huge, and I mean huge. To give you an idea of the space, here are some numbers: More than 100,000 people attended the Kentucky Oaks, and more than 150,000 attended the Kentucky Derby, which is a lot of people landing in one place at one time.
(Here’s my dress, here are my shoes, here’s my purse, and here are my sunglasses.)
Churchill Downs is not only known for the Kentucky Derby, but it’s also known for its iconic architectural design. I was super excited as we approached the white gates with “CD” emblems and the famous spire towers that peek out.
Speaking of approaching, we were lucky enough to have our own driver with a credential who could drive us right up the building and drop us off. There were people selling parking spots in their front lawns from about half a mile out approaching Churchill Downs, and making that walk wouldn’t have been fun in heels. (The homemade signs and people in chairs on their driveways was just another clue that Derby weekend is a big focus for the city and residents of Louisville.)
During our time at Churchill Downs, we got to experience two separate ticketed areas. Let’s discuss them both …
Enjoying First Turn Reserved Seating for the Kentucky Oaks on Friday
Day one, the Kentucky Oaks.
We started out in the First Turn Reserved Seating, and this area had our assigned seats, a few cocktail tables, wagering and concessions — it was covered, but outdoors.
We spent all day during the Kentucky Oaks here, and the weather was beautiful, mostly, outside of one 15-minute severe-weather moment. This was a great way to soak up the racing, the betting, the food and the drinks with some sunshine and some breeze. We arrived before the first race and stayed all day until the last race in this same spot. We even made some friends at a nearby cocktail table who helped us choose the winning horses. Also, we both wore pink to the Oaks, which is suggested, and I’d say about 80 percent of people were in pink along with us.
While we enjoyed our time in First Turn Reserved Seating, there’s one thing worth mentioning — the bathrooms. Here’s where I’ll get real: The public bathrooms in this area were actually not nice at all, which was a disappointment. They were constantly out of toilet paper or paper towels and some of the sinks didn’t work either. I was actually pretty surprised that the facilities were as outdated as they were, based on how fancy everyone was dressed and how much it costs to access this area.
There were also times when I would look around the main areas of Churchill Downs while walking around, and I felt like some things weren’t quite “show ready” (a phrase I’ve held onto since starting my career at Disney), such as lines of recycle bins outside the gates and crown molding hanging from building corners. I mentioned this complaint to a local Kentucky friend, who we were able to catch up with at the Derby, and he said that it almost doesn’t matter what the place looks like, because people will pay just about anything to be at the Derby, so there’s no real need for Churchill Downs to improve or try too hard. Good to know.
Overall, day one at the Kentucky Oaks was such a fun, lovely and exciting day of horse racing, eating, drinking and wearing pink. I kept thinking and saying how totally cool it was to be there doing it, and that’s an awesome feeling.
(And one more thing to note: We did the research, and a single ticket at First Turn Reserved Seating starts at $1,300 per person — wow.)
Enjoying the First Turn Club Dining for the Kentucky Derby on Saturday
Day two, the actual Kentucky Derby, was a bit different.
While we started out back in our same seating area on day two, the cold, windy and rainy weather were not enjoyable at all, and we also didn’t score our own cocktail table that day (these tables are first-come, first-serve). I had brought Dave’s blazer from the day before to cover my upper body, but I was shivering and freezing in my dress and heels, with no access to warmth. Honestly, the day didn’t start out great, and I was worried about our overall experience if we had to last all day there, because the Derby is a really long day … but then, something good happened.
I’m happy to report that Dave’s old coworker from California who was working at the Derby was able to bring us down to a nicer area with an indoor/outdoor set-up, and this spot was just awesome. We spent most of the second day in this new spot, the First Turn Club Dining, and this was just totally excellent.
The food was elevated, the space was fancy, the bathrooms were immaculate, and we could be inside to stay warm, or walk outside to a patio that came right up to the track. This is where we watched the actual Derby race (in ponchos), just feet from the horses and jockeys racing by in the rain.
We just-so-happened to know one person from Charlotte and some old friends from California who would be in this area (including the former coworker who brought us down), so it was also a good time to have plenty of people to hang with.
I said to our group that I’m really glad we had both experiences, because we got totally different Kentucky Oaks and Kentucky Derby vibes. I liked different things about each spot, and it worked out perfectly to try them both out.
Day two was a little more crowded and wild than the first, and I had a true blast, starting from the moment we moved down to the nicer area.
(And another note: We did the research, and a single ticket for the First Turn Club Dining starts at $2,500 per person — just WOW.)
Soaking up the outfits and people watching at the Kentucky Derby
Let’s get into my favorite parts … the outfits and the people watching.
Seeing people’s outfits at the Oaks and the Derby was even more enjoyable, entertaining and impressive than I could have imagined. There were a small amount of people who kept it casual, but on the whole, people were dressed to impress in every way. The colors, the hats, the creative choices — it was all so good. I could have situated myself facing the crowd, away from the tracks, and would have been completely happy staring at people all day.
(Here are my earrings, and here’s my lipstick.)
I was pleased with my outfits, but if I ever go again, I’ll go bigger and bolder with my dress, hat and accessories. If there’s ever a time to do so, it’s this. Major props to the people who clearly made or had made parts of their outfits, because that’s extra. Also major props to the couples who wore matching get-ups. I literally couldn’t get enough of the people watching. It was the best I’ve ever seen in my entire 40+ years of life.
Now, from the outfits to another good part, the refreshments …
Partaking in the food and drinks at the Kentucky Derby
Most tickets to the Kentucky Derby are all-inclusive of food and drink, outside of the cheaper in-field tickets. Depending on the area where your tickets give you access, you can grab as much of the food and drinks as you want, all day long. We didn’t know this ahead of time and thought we had extra special tickets that allowed us this option. Turns out Churchill Downs keeps it simple by letting nearly everyone access all the food and drinks they want while at the Oaks and the Derby.
The signature drinks of the event include the red-colored-vodka-based Oaks Lily (I liked this drink and had one), and the brown-colored-bourbon-based Mint Julep (I didn’t like this drink, and I only had a few sips of one). These drinks were flowing, but you could also get wine, beer or spirits of your choice, and I mostly stuck to wine.
Food wise, First Turn Reserved Seating had regular sporting-event food (like hot dogs, hamburgers, chicken fingers, etc.) and First Turn Club Dining had fancier buffet food (like quinoa, chicken, fruit, rolls, etc.). We also got some fun empanadas, frozen cheesecake on a stick and other more creative fare from the main areas outside of First Turn.
On a whole, the drinks were great, the food was fine, and it was really neat to not have to pay for any of it once you were inside the main gates.
Overall thoughts on what it’s like to go to the Kentucky Derby and Kentucky Oats at Churchill Downs
Fun. Eventful. Colorful. Fancy. Full of tradition. Exciting. Awesome. Long, yet short.
Yes, our tickets were so good (and I’m not complaining, especially because they were free), but apparently there are plenty of incredible places to watch the Derby, much fancier than where we were.
I had hoped to have some real-life celeb sightings, and there was a red-carpet entrance on the other side of the building where the big-name folks came in, but we only saw them on the screens. Nonetheless, it was neat to know so many athletes, actors and social media personalities were there watching the Oaks and the Derby at the same time as us.
I’ve been to some pretty exciting events over the years through Dave’s work, and I will say that the Kentucky Derby is up there as one of the best. I didn’t know what to expect, and I think it beat my expectations entirely, even if we did have some rain and sometimes had to fight for paper towels in the bathroom.
(Here’s a similar style to my dress, here are my shoes, and here’s my purse.)
Our time at Churchill Downs flew by, and I’d love to go back in the future and experience it all again. But if not, this item is still totally crossed off the hope-to-do-one-day list.
Here’s what you should know before you go to the Kentucky Derby
Thinking of going to the Derby? Do it! Here’s what you should know before you go …
- Book far in advance. Tickets sell out. Flights book up. And reservations and hotels are hard to come by. We talked to people who booked their dinners each night six months before the event. We talked to people who stayed in AirBnBs an hour from Churchill Downs. We talked to people who flew into and out of Cincinnati and made the 90-minute drive instead of flying into Louisville.
- Know that the days are long. If you want to see all the races, you’ll be arriving mid-morning and leaving in the evening. I had no idea the Oaks and the Derby were such long days. We clocked about seven hours there on the first day and seven hours there on the second day.
- Be prepared for any weather. We came armed with ponchos (big thanks to a member of our party for thinking ahead and bringing them), even though the forecast had been good leading up to the event until about the day or two before. You cannot bring an umbrella, but you can pack a poncho. The weather can change at any time, so be ready to layer up.
- Visit the merchandise stores early. We went to multiple stores on the first day, Kentucky Oaks day, and some of the good stuff was already sold out by noon. In fact, you were supposed to get a nice blue Derby tote bag at most stores with your purchase and those sold out early too. By the way, if you shop at the Derby Museum store, you don’t get a nice bag, but you do support the museum, and that’s what we did. I love the little Derby bracelet I bought, and Dave got a poster and a t-shirt as mementos. I really wanted a Kentucky Derby sweater with stitching on the front, but it was $190, so I passed. Yes, much of the merch was pricey, as you can expect.
- Bring a big purse or an extra foldable bag in your purse. Surprisingly, the bag policy at Churchill Downs is way more lenient than most sporting events I go to. You can bring a regular purse or tote that’s smaller than 12x6x12 inside with you. I had a really small purse, and I wish I had brought one a little bigger to hold more things. By the end of the day, I had accumulated cups, a program, souvenirs and more, and it was hard juggling it all. Had I snuck a tote bag in my little purse, I could have easily moved everything into it later, and that’s what I’d do if I went again.
- Know that you might be standing a lot. I wore heels all day at the Oaks and at the Derby and I don’t think I ever sat down. While my feet were uncomfortable, I managed. I would say the majority of women were in heels, and I’m glad I wore heels both days simply for appearance sake. I did see some people with an extra change of shoes, and while that’s a good idea, I didn’t end up needing spares. Just be ready if you’re someone with sensitive feet. We had reserved seats but hardly ever sat down, and I noticed a lot of people doing the same thing.
- Bring cash for betting. Yes, you could visit the ATM, but it’s much better to have cash on hand for betting or for tipping. And if you bet, hold onto your ticket. Also, if you really want to do some smart betting, read up on how to utilize the stats in the event program. It looked like gibberish to me, but we learned that there were helpful details on each horse, if you knew how to decipher it all.
- Eat and drink all the things. This is a really cool fact, but most tickets to the Oaks and the Derby include unlimited food and drink from the general concessions. You don’t have access to that if you get the cheaper in-field tickets, but the rest of the tickets do include this. It feels so fun to grab whatever you want to eat and drink and not have to pull out your wallet. Depending on where you sit, your food and drink options will change. We got to experience two ticket levels, and the differences were big. Don’t forget to drink plenty of water, because it’s free too.
- Dress to impress. The outfits were the best part. There is no such thing as “too much” at the Derby. If you ever get to go, go all out with your look. Homemade items can be fun too, but we did store bought. I loved dressing up for this event, and I loved watching what other people were wearing so very, very much.
I still can’t believe we went to the real-life Kentucky Derby, and I’m sure I’ll be thinking about it for quite some time. What an experience being a part of the oldest consecutive-running sporting event in history. Riders up!
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Questions of the day
Have you ever watched the Kentucky Derby?
What’s one event on your bucket list?
