A First Time Experience at The Kentucky Derby

Submitted by RCS Reader and all around cool guy Simon Chio

When Laura, a dear, childhood friend of mine, asked if I wanted to go to the Kentucky Derby this year, I assumed she meant to a party in Atlanta. Being the horse racing fan that I am, of course I responded yes. Little did I know, we weren’t going to just any old Derby party. We were going to The Run for the Roses at Churchill Downs.

For weeks, I couldn’t contain my excitement. I have zero doubt that my girlfriend, Meghan, was beyond annoyed by our numerous conversations about the trip. From juleps to jockeys and wardrobes to wagers, I told her anything and everything that was on my mind about my very first Derby trip (and her second). However, this wasn’t a drive for seven hours to stand in the infield trip. Laura was a seasoned Derby veteran who had arranged for not only my first trip to Churchill Downs, but the trip of a lifetime.

On Friday night, we run to the grocery store to stock up on food and drinks for the trip. One of the neat facts about the Derby experience is that you can (and should) bring your own food into the track. I was warned in advance that the concessions were pretty terrible so like any good guests, we are happy to provide the food. Meghan and I make a tub of curry chicken salad and a tub of almond chicken salad, as well as pick up some Palmetto cheese, crackers, and cookies. With the prep work for Saturday done, we turn in early.

Our alarm is set for 6:30 a.m. on Saturday morning, but like a kid on Christmas day, I’m too excited to sleep so I’m wide awake at 5:00 a.m. I’m checking the weather in Louisville, and the forecast calls for intermittent rain and a high in the low 60s. Nothing to be concerned about. After we finish our morning routine, we get dressed in our ever important Derby outfits. Meghan looks gorgeous in a black and white dress and black hat (that’s as good as I can describe women’s fashion). I choose a pink Bonobos unstructured sport coat, Charles Tyrwhitt white dress shirt, blue Vineyard Vines tie adorned with race horses, J. Crew Bowery Slim stretch chinos in French navy, La Matera Mendoza belt, brown Allen Edmonds Verona II bit loafers, my TAG Heuer Aquaracer watch, and my trusty Ray-Ban sunglasses. Next, we load up the car and head north on 75 to Cobb County International Airport 40 minutes before our departure time. Like I said, this isn’t your standard Derby trip: we are flying private out of McCollum Field in Kennesaw. And because we are smart people living in the South, Meghan and I stop at Bojangles for a quick bacon, egg, and cheese biscuit breakfast.

We meet Laura and our three other friends at the airport at 8:45 a.m., and “wheels up” is at 9:00 a.m. The pilots greet us inside the terminal, and once the plane is fueled up, we board and get settled for the short, one-hour flight to Louisville. If we boarded the plane at 9:00, I’m pretty sure the first mimosas and screwdrivers were flowing at 9:01. After lots of funny stories and cups full of liquid breakfast, we touch down in Louisville. The airport there is littered with private jets and shuttles. We have a little confusion with our driver, but we finally get picked up in the slickest Mercedes van ever and head over to Churchill Downs. Again, there are more mimosas, Miller Lites, and Titos to be had. One thing we drove by was this very sad outdoor concert near the track. There are literally 8 people in the crowd, but kudos to the band for putting on what I presume was an awesome show for their loved ones.

Our driver parks the van, and we head into Gate 17. The process of getting into the venue and finding our seats is incredibly quick for an event that has 158,070 people attending. Our group of six is sitting in the first floor clubhouse just past the finish line, and to top it off, our box of seats is covered so the weather is not a concern. (Also, sitting right behind us is a great family I know from Atlanta. Small world.) Once we find our seats, we walk down closer to the track for some pictures and to take it all in. Churchill Downs is a beautiful place, and I am already in awe of the pageantry of the whole event and experience. Afterwards, we head to place our first bets on Race 4 and to procure our first mint julep of the day. The betting process is easy, and there are betting windows everywhere. The attendants are very friendly, and it takes less than a minute to place each bet. I make a place bet for the upcoming race to see if Lady Luck will be by my side this cool Saturday in May. (Spoiler alert: Lady Luck is nowhere to be seen for the next 7 hours.)

The julep, on the other hand, is good to me throughout the day. For $14, you get a potent yet delicious mint julep in a commemorative glass. I was actually surprised that they serve it in a glass and not in a plastic cup, but the vendor reminds me that the glass is the best way (and much cheaper than a sterling silver cup) to keep the julep vessel cold and frosted. For reference, a Bud Light is $10 so the $14 mint julep and collector’s glass is a good deal. Meghan opts for a Lily, a vodka and cranberry juice cocktail, and we settle into our seats. One thing we didn’t take the time to do is walk around Churchill Downs. Also, we didn’t head out to see the front entrance and the twin spires, but I’m confident I’ll be returning in the future.


There are 14 races on Derby day, and we are there for races 4 through 12 (the actual Derby race). Meghan hits a bit of a hot streak and starts giving betting advice to strangers. I lose one wager after another, and Laura and the rest of our group are just as unfortunate. But we all still hold out for a win (or a place or a show or anything at this point) on Race 12, the 143rd Kentucky Derby at 6:42 p.m. I have placed a box exacta on #5 Always Dreaming, #14 Classic Empire, and #15 McCracken, as well as some Win/Place/Show bets and other individual wagers. I order another julep, go back to my seat, and stand with the crowd to sing “My Old Kentucky Home” as the twenty thoroughbreds and their jockeys parade onto the track towards the starting gate. Once they are all in the gate, The Most Exciting Two Minutes in Sports starts, and we are in prime position to see the competitors begin their first turn and again when they come through the homestretch towards the finish line. As you know by now, Always Dreaming holds off the field to win by 2 3/4 lengths over Lookin at Lee and Battle of Midway. The crowd is going nuts, and I can’t believe I just witnessed my first Kentucky Derby.

We actually head out to the parking lot to find our shuttle back to the airport after the Race 12. Laura let us know that the only way we don’t sit on the tarmac all night is to beat the crowd and head back to the plane as soon as the main race is finished. Also, you can redeem your winnings by mailing the ticket to Churchill Downs so no point in standing in line to cash it in. Luckily for our group, nobody won so we just all saved ourselves the postage.

We meet up with our pilots, board our jet, and fly into the sunset back to Atlanta. After a long day. we are back home by 10:00 p.m., but it is a day I will never forget. I’m sure spending the day in Millionaire’s Row and going to the after parties can be fun, but I wouldn’t trade the experience I just shared with my group of six for the world. Thanks to a wonderful friend, I was able to check an item off of my bucket list. The memories from the 143rd running of the Kentucky Derby will forever be far more valuable than any winning ticket.


1 Comment

  1. Jay
    05/17/2017 / 9:55 AM

    ….that never happens to me.  Ever.

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