Last year, I went back to my home state of Kentucky to revisit the Kentucky Derby for the first time in a few years (“Review Editor Revisits Kentucky Derby Roots,” The Oberlin Review, May 10, 2024). This year, I decided to take two newcomers, News Editor Layla Wallerstein and former Bulletin Editor Eloise Rich, into the infield at Churchill Downs to see what it’s like from an out-of-town perspective. This is our recollection of the day.

Did you have any past experiences with the Derby?

LW: I had no experience with the Kentucky Derby. I actually barely even knew what it was. I had heard of it before, but when I was invited I did have to look it up to remind myself.

ER: I grew up watching the Derby every year with my dad. He’s always had an affinity for horses, and since he passed away I haven’t been watching the Kentucky Derby. So there was a year where I did not watch the Kentucky Derby, but otherwise, I was very consistent with watching it every single year, and it was always just a great time. We’d make a day out of it. In my childhood, of course, I was not drinking bourbon.

We started by grabbing a cup of local coffee before heading to the western-wear shop, Tecovas. Although Layla and Eloise were already equipped with fabulous headwear, courtesy of my mom, I decided it was time for me to become a true, grown Kentuckian and purchase a hand-tailored straw cowboy hat — I was looking at a more traditional rabbit-fur hat, but was advised that we’re in “straw season.” While in the store, we sipped complementary mint juleps, our first of many, and admired the boots while enjoying a live bluegrass band.  

We then headed home, got dressed to the nines, and headed for the track. The energy was palpable as we followed the hordes of college students making their way through the tunnel into the infield — the cheapest tickets, but arguably the most fun. Despite the light rain, the crowd seemed aglow with the excitement of the day, and perhaps a little bourbon.

What did you expect going in? Were your expectations met?

LW: Because I didn’t know much about it going in, I didn’t have many expectations. I expected a lot of really extravagant hats and outfits, and realized that that image perhaps corresponded to more posh attendees up in the balconies rather than on the infield. Instead, there were lots of young 20-something-year-olds milling about in mini dresses and drinking. I was also surprised by how brief the race was. It’s kind of funny to be waiting there for several hours, and then you have two minutes for the actual race. 

ER: I feel like a lot of the time watching it growing up, it was like a fashion show. That was a big part of it for me. There was sort of a shortage of obnoxious hats because of the rain. To be frank, I didn’t expect it to be as fratty as it was on the infield. And it’s not to say that that was a bad thing, but it was a very different experience than the one they portray on the television.

After we had settled into the environment and made our way around, we started connecting with my old pals that had all come home from school for the big day. Some lent cigars, others drinks, others a spare poncho, but our time between arriving at 3 p.m. and the race at 6:57 p.m. was spent jumping between various locations — and different groups — dancing, drinking, and betting. We eventually found a space right next to the fence of the track, and held our breath as the horses whooshed by in the blink of an eye. Sadly, our staff pick, Journalism, placed second, while my personal favorite, Publisher, fell far behind in 14th.

Like the rest of the crowd, we cleared out after the race had ended, ready to either eat and sleep, or drink even more — one was bound to happen. We attempted navigating the hysteria of downtown Louisville traffic post-derby, but gave up on waiting for a Lyft and walked the two miles to my personal Louisville drunk-snack of choice, El Nopal, the Kentucky equivalent of Oberlin’s Lupitas Mexican Restaurant.

What was the highlight of your experience, and the lows?

LW: I do think it was really cool to be partaking in this whole kind of cultural phenomenon that I really didn’t know very much about. And this is clearly something that a lot of people there go to every year. I also liked how friendly and welcoming everyone was, and overall, I had a really fun time. The low was definitely that Journalism didn’t win.

ER: As Layla was saying, it’s an interesting sort of meditation on Southern culture, or a very specific section of it, and seeing how young people are responding to this longstanding tradition. I mean, people do this every year, and I really enjoyed the experience of being a part of that. I gotta say, the high was probably the drinks, truth be told — they’re delicious, the mint juleps. Oh, my god — but the low was my four-day hangover.

After we finished our hearty meal, happy to be finally out of the rain, my parents picked us up and took us to their favorite drinking spot, The Bonnycastle Club. We chose drinking more over sleeping, shared a few Kentucky cigars, and laughed about all the antics of the day. Finally, we headed home to get a good night’s sleep in order to preventatively mitigate our future hangover and prepare for our 10 a.m. departure.

Any advice for someone wanting to experience the Derby for themselves? Was it worth the journey?

LW: I would say wear practical shoes that are comfortable, but also be very open to being social.

ER: You have to go with friends. Go with a Kentuckian, someone who knows it. While I know how to navigate a crowd in sort of an unfamiliar, social setting, it’s very daunting. It’s chaotic, beautifully chaotic. I also wore a long dress, and while it is a very beautiful dress, it is covered in mud. And so, as much as I am not necessarily a huge fan of a mini dress, I do understand why everyone wears a mini dress and a sort of Spirit Halloween-esque fascinator headband. It doesn’t need to be the pinnacle of class, but in my opinion, the best part is dressing up. I would love to go again.

Everyone should experience the Kentucky Derby live and in person at least once in your life. I highly encourage every reader to make the pilgrimage to Churchill Downs, grab a mint julep, and place a bet whenever you can.