Peter and I attended the Kentucky Oaks and Derby this year! Finally!
Peter has family in Kentucky and they have wanted us to visit during The Derby for many years. We made an attempt at this adventure in 2017 but failed because of flights. The Louisville airport is tiny and most flights for The Derby sell out nearly a year in advance.
This was a lesson learned and we used our new knowledge and booked our flights for the 2018 Derby in September 2017. The best we could do at that time was a non-stop from Seattle to Indianapolis for $500/ticket! Seattle is so goddamn far away from everywhere!
This lass was doing her horse research on the flight to Indy which was dubbed the “Derby Express” by the flight crew.

After four hours of flying, we hopped in a rental car and I drove another two hours from Indianapolis to Louisville and we went to a good ‘ol fashioned house party. A few local dishes were served at the party including:
- Derby pies which is pecan pie with chocolate
- Mint julep gummies
- “Country ham” (I still am unsure how this differs from non-country ham or any ham for that matter)
- Benedictine spread which is a cucumber and cream cheese spread and tastes a bit like tzatziki but thicker
- Bourbon seasoned Chex Mix
- Other miscellaneous foodstuffs all flavored with bourbon
Following several beers and toward the end of the evening, we played Derby trivia and then were taught how to read race cards.

I found race cards to be confusing especially after an early morning, seven hours travel and a couple of beers. They contain a lot of tiny numbers and fine print and abbreviations. It would take hours, days, possibly years to fully understand the data even under the best sober conditions.
What I learned:
- Always place your bet by stating the number of the horse, not the name of the horse.
- Always check your betting ticket for accuracy before leaving the betting window.
- Always “box in” your bet. Example (with assistance from my cousin-in-law): You want to bet on a 10 horse race and you like the #4 and 7 horses. Your crystal ball says that 4 will win and 7 will come in second. If you place an exacta bet where you designate the first and second place winners and 4 wins and 7 comes in second, then, fuck yeah, you win and you’ll win more than having bet on the winner. However, if 7 wins and 4 comes in second, then you get nothing with an exacta bet. To add an additional layer of safeguard, you can “box your exacta” and you win with either combination, either 4-7 or 7-4. Boxing your bet costs more but increases your odds of winning.
- If you want to know if a horse is running well, they’ll be running a furlong (1/8 mile) in 12 seconds.
- Horses don’t hit “horse” status until their fourth birthday. Until then they are simply colts and fillies.
We left the house party around 1am and hit the hay because we had a long day ahead of us with our chaperones who, at most times, had more energy than we did.

The Kentucky Oaks (“The Oaks”)
Friday is the day of the Kentucky Oaks which is the sister race of the Kentucky Derby. The Oaks is restricted to female horses (“fillies”) three years old or younger. The official color of The Oaks is pink and the official drink is the Oaks Lily (also pink). It is highly recommended to wear pink when attending The Oaks.
Historically, The Oaks has been the day more-locals-than-tourists visit the track but there has been an uptick in tourists visiting the track in recent years on Oaks Day. Churchill Downs did not feel crowded to me on Oaks Day even though there were tens of thousands of people in attendance. We were able to zip through crowds pretty quickly and there was no one in the security queue when we arrived around 1pm after a hearty brunch.
There are many races during the course of the day and they post close to one another early in the day but as the day goes on, the post time increments increase and so by the end of the day, you could be waiting one hour between races. This makes for a very long day.
I assumed that the official Oaks and Derby races were the last races of the day but that’s not true, so make sure you are clear on which race number of the day is the official race so that you don’t miss it!
The winner of The Oaks race is handed $600,000 of the $1 million purse and a garland of lilies, affectionately known as Lilies for the Fillies.
The weather was warm and humid and the rain held off so we were happy considering we did not have covered seats. In fact, we did not have seats at all. We purchased “Infield & Paddock” tickets which basically gets you in the door and not much else. With tax and TicketMaster fees, we paid $50/ticket for our Oaks Day tickets. This included a $10 discount for purchasing early.

We began our journey by walking through a tunnel below the track to get to the infield which is the middle of the track. I was surprised by a few things during this short journey. Smoking was permitted, kids were running about and people were carrying actual glass glasses.

From the infield, we walked through a second tunnel below the other side of the track and emerged between the track and the stands but still in the tunnel (the roof of the tunnel was missing). The final leg of our trek was to walk below the stands and ’round the corner to the paddock.

The only paddocks I’ve seen in my life were in England. Below is a grainy photo of a paddock I took in 2011 on an iPhone 4. Dexter and Shadow had stayed at the home of the lady who owned the paddock and the dogs would run around in the paddock during the day. In the middle of the paddock was an open-top wire chicken coop. Dexter spent his weekend terrorizing the chickens in the coop and eventually killed one of the chickens.
Dexter was pleased. The dog boarding lady was angry. I was proud. Needless to say, the dogs were not allowed back at that dog boarding facility.

When I heard we’d be going to a paddock, I thought we would be heading out to a green field slightly off in the distance and was surprised to see the paddock on the other side of a concrete wall. Before the race, the horses are paraded around a miniature oval-shaped cobblestone track.


It only took a couple of minutes to snake myself to the railing of the paddock so that I could photograph of horses instead of hats.
Whilst I enjoyed our short time watching horses at the paddock, I was not enjoying the $14 “keep the glass” mint julep in my hand. I was powering through it though as to not offend anyone. I left Churchill Downs with hair sprouting from my chest from this drink. I have proven again that I am not a bourbon, whisky, scotch drinker.

The next stop on our Churchill Downs tour was to the restroom followed by the bar where we purchased a four-pack of Oaks Lilies. The Oaks Lily tastes a bit like a sweet cosmopolitan. Our drinks were also $14 and served in glass stemless wine glasses. Peter and I enjoyed the Oaks Lily drink and soon enough, our group had accumulated 10 stemless wine glasses and four mint julep glasses.
I’m OK with one commemorative glass but the amount of glassware we were stockpiling was stupid. I asked the bartender if she could reuse my glass and she said no.
From the paddock bar area, we walked back to the infield and found Peter’s cousin and a lot of the attendees of the house party from the night before. The infield area where they were seated was around turn 1 and it was empty.
Ironically there is very little, if any, view of the track from the infield. A chainlink fence separates the infield from the grass and dirt tracks. In some areas of the infield, the ground slopes down toward the fence so you end up standing on ground that is lower than the track itself which obstructs the view.

We spent about five hours at Churchill Downs on Oaks day and it felt like a very long day because 98 percent of that time was spent standing and walking around and taking photos of people when they weren’t looking.

By the time we left, people were extremely intoxicated and the grounds were littered with trash. I was astonished by how little regard people had for disposing of their trash in one of the many thousand bins on the grounds and asked who was responsible for cleaning up the mess. My aunt explained that groups such as the Boy Scouts come in with lawn equipment and clean it up as part of their required community service hours.
During the course of the day, I saw two females puking. Multiple people were being held/propped-up because they could not stand themselves.
You see the Kentucky Derby on the telly and it’s portrayed as a posh event with pretty dresses and hats and celebrities but the reality is that it is a big redneck party.
The Kentucky Derby (“The Derby”)
Did you know that there are all sorts of Derby races? I did not know this until Peter and I attended the Kentucky Derby. A Derby is a type of horse race named after the Derby Stakes run at Epsom Downs Raceway in England. There’s the Florida Derby, the New Zealand Derby, the Hong Kong Derby. The list goes on and on and on.
As with the Oaks, there are many races during the course of the day and the post times get further and further apart as the day goes on. The winner of The Derby race is handed $1,240,000 of the $2 million purse and a garland of roses which is made at a local Kroger grocery store.
The weather was absolute shit when we arrived at Churchill Downs and it got worse from there. We again had “Infield & Paddock” tickets for Derby Day which meant no seats. Including tax and TicketMaster fees, we paid $76/ticket. This included a $10 discount for purchasing early. I felt this price to be pretty steep considering you get absolutely nothing with this ticket aside from entry.
The walk from the parking lot at Papa John’s Stadium to Churchill Downs was about a half-mile and it was pouring rain. I was wearing a dress, raincoat, and Tom’s shoes. Peter was wearing shorts, a polo shirt, and Adidas shoes.
We were soaking wet by the time we reached the security entrance. The water ran off my raincoat and dumped onto my dress so it looked like I wet myself. It was cold and we were miserable but neither of us wanted to admit defeat quite yet, considering we had paid $150 to be there.
Our first task after entering Churchill Downs was to find a bar that made bloody marys. We knew this would be a difficult task in bourbon country but I saw vodka at the first bar kiosk we came across so we took our chance and jumped in the queue of 30 people. It paid off and the bloody marys were good and made by a chap from North Dakota of all places.
Our second was to find somewhere to stand that was covered because it was pouring rain. I swapped out my rain jacket for a poncho we purchased at Plitvice Lakes National Park in Croatia several years prior. A quick glance at my shoes and you can see how soaking wet they were.

We stood in the covered area for about 20 minutes, just long enough to finish our drinks. The constant stream of cigarette and cigar smoke was getting to us so we decided to walk toward the paddock area, get another bloody mary and hopefully find a place to stand that was covered. We found ourselves in the “strip mall” below the seating.
Not too long after arriving did the cigarette and cigar smoke get to us again and we decided to cut our losses and leave Churchill Downs but first we had to place our bets for the big race.
As we were about to leave, I received a text from Peter’s cousin with some betting advice. She explained that we needed to bet on horses that run well in muddy (my) or sloppy (sy) conditions. The track at this point in time was deemed “muddy” but it wouldn’t stay that way for long.

I placed my bet on Audible across the board. Audible came in third so I won but I bet so little that there was no payout and now I have the ticket as a souvenir.

The walk to the car was long, wet and cold. Water was squishing through my toes as I walked. The parking lot had filled up since we’d arrived and people were tailgating with loud DJ-style music. I personally do not see the appeal in packing up your shit, driving to a parking lot and paying $20 to park only to stand outside and drink in the cold pouring rain but everyone is different.
Mother Nature started dumping down buckets and buckets of rain almost immediately after we closed the doors of the car. The visibility was low. Roads soon became flooded. I have only seen rain this hard one other time in my life in England and it only lasted about an hour. The hard rain on the Derby Day lasted nearly four hours, making the track very, very sloppy.
I believe total rainfall was short of 7.6 cm / 3 in and the 2018 Kentucky Derby has officially been named the wettest Derby on record in its 144 year continuously running history.
We spent our afternoon indoors “exploring” the bars of Bardstown Road. The rain stopped shortly after the official Derby race and we ventured outside to the upper deck of Gravely Brewing Co for a vista of downtown Louisville. I was struck by how tiny it is.

Would we do the Kentucky Derby again? Yes but we’d do it differently and here’s what we’d change.
- Arrive earlier in the week and partake in one of the many festivals, parades and get-togethers the city puts on for the weeks leading up to Derby weekend.
- Though we preferred Oaks Day, we’d skip it and buy tickets with actual seats (e.g. grandstands) on Derby Day so that we had somewhere to sit and could actually see the horses race.
- Attempt to smuggle in booze.
- Bring snacks.
- Bring proper, non-disposable ponchos.
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