The Kentucky Derby, with its unparalleled history and tradition, is a bucket-list sporting event. Every year, more than 150,000 spectators gather at Churchill Downs in extravagant hats and pastel suits to sip mint juleps, wager and watch the Run for the Roses, which has been called the "greatest two minutes in sports."
The Derby takes place the first Saturday of every May, but preparations for the iconic race start well before. As milliner Lisa Shaub told me, those who are really looking to go all out on their outfits start calling for custom-made hats as early as February. Those looking to go all out are also spending thousands of dollars: There are several ticket options that exceed $4,000.
I found out the week of the 144th Kentucky Derby that I'd be attending and scrambled to put together an outfit and make semi-affordable travel plans.
To say I was a Derby rookie would be an understatement: I'd never had a mint julep and didn't know what a fascinator was until I bought one a few days before the race. I'd also never seen a horse race, live or on television. To further complicate things, I'd be completely on my own.
I started uncertain and alone in elite box seats, then joined the rowdy scene on the infield and ended up in a large, quintessentially Southern home with 15 new friends.
Here's exactly what it was like to spend a full day at the Kentucky Derby — starting as a newbie and leaving as a fan.
Flights into Louisville were close to $1,500, so I flew from New York City to Indianapolis for less than half that amount. Hotel and Airbnb options in Louisville were scarce and well above my price range. Over Derby weekend, the average nightly cost for a two-person stay in Louisville is $1,197.
My best option was a $266-per-night hotel room in Lexington, which is about 80 miles east.
It was an easy hour and a half drive to Louisville on Saturday morning, until I got close to the track. Streets were closed off and the traffic was bonkers. About two miles out from Churchill Downs, I started seeing neon signs for parking: "$5, plus $2 for a ride to track."
The closer I got, the higher the prices went. One Louisville-native told me that residents near Churchill Downs not only open their homes for parking but also sell beer and homemade food and can earn enough over the weekend to make a monthly mortgage payment.
I was lucky and had a pass that granted me parking outside of the Clubhouse Gate, one of the three entrances to Churchill Downs.
Gates open as early as 8:00 a.m. I arrived around 11:15 a.m. and there was already lots of activity at the entrance. I later learned that I showed up on the earlier side, and what seemed like a lot of action to me was nothing compared to the afternoon crowds.
It was drizzling when I arrived but umbrellas, this Derby rookie learned, are one of the prohibited items at Churchill Downs. This shot was taken just before I had to toss mine at security.
Immediately upon entering the racetrack, I was greeted with the holler of: "Mint juleps! Mint juleps!" At first, the consistent hollering was all I could hear, but I quickly adjusted, like one does to the sounds of sirens in New York City, and it simply became background noise.
The mint julep is the traditional derby drink. Each year, about 120,000 juleps are served over the two-day event, which require more than 10,000 bottles of Old Forester mint julep ready-to-serve cocktail, 1,000 pounds of mint and 60,000 pounds of ice.
Despite the rain, which started to pick up, the colors and patterns took center stage. The Derby gives people a license to get creative and be bold. The big hats didn't disappoint.
Nor did the outfits.
Navigating Churchill Downs was like making my way through a small city. It's massive, with endless bars, concessions, shops and ATMs. I withdrew 60 bucks and reluctantly ate a $5 ATM fee. While in line, I overheard someone lament, "I thought $600 would be enough for the day ..." It sounded like it was this person's second trip to the ATM.
There were also big screens broadcasting the races scattered throughout the grounds.
At the "red carpet" area, the rich and famous made their way into the racetrack. This year's celebrity guests included Green Bay Packers quarterback Aaron Rodgers, "Black-ish" star Anthony Anderson and Olympic skaters-turned-announcers Johnny Weir and Tara Lipinski.
At the center of Churchill Downs is the Paddock Plaza, where you can watch the horses get prepped for each race.
I stopped by the $1,000 mint julep tent, where the super rich can pick up their four-figure drinks. Woodford Reserve, the presenting sponsor of the Derby, made 105 limited-edition cups — 90 $1,000 sterling silver "Bluegrass cups" and 15 $2,500 gold-plated "Commonwealth cups" — for this year's Derby.
I watched as a bartender prepared a "$1,000 mint julep" for one of the 90 spectators who pre-ordered a Bluegrass cup.
The offerings at the concession stands seemed endless. I saw a lot of people eating pulled pork sandwiches and bratwurst, and the chocolate-covered fruit kabobs were enticing. Overwhelmed by the options, I panicked and grabbed a $6 pretzel from the vendor with the shortest line.
I also learned that you can save a lot of money by bringing your own food items or "box" lunches if they're in clear, plastic bags. Plus, you can bring in water and soft drinks if they're in sealed, clear plastic bottles.
If you're not in line for food or drinks, you're probably in line to bet. There were self-service wagering machines and wagering windows everywhere.
Including $50 minimum windows.
Betting at the Derby can get complicated: There are multiple ways to bet, plus specific language you're supposed to use.
If you're placing your bets at a mutuel window with a mutuel teller, you lead with the race number you're betting on, since there are many races throughout the day. Then, you state the amount you're betting, the type of bet you're placing and the numbers of the horses you're picking. After placing your bet, you get a ticket, which you'll need to cash out if you win.
I'd never placed a bet on a horse race. A friendly woman recommended I bet on the "mudders," horses that can run on a muddy track, but I kept things simple and put $5 on the one horse I knew, No. 5 (Audible), to win it all. That way if I lost, which I did, I'd only be out the cost of a pretzel.
The first race went off at 10:30 a.m. and they continued throughout the day, with 30 minutes to an hour in between each one. Whenever a race started, everyone on the grounds directed their attention to the nearest TV. The cheering and excitement escalated as the horses got closer to the finish line.
I had access to the second and third levels of the clubhouse, where there were box seats with a nice view of the track.
There were also nicer amenities in the clubhouse area and the lines for everything were shorter. Perhaps the best perk was that it was completely shielded from the rain, which came down harder as the day progressed.
Everywhere I turned, I saw chic dresses, pastel suits and extravagant hats.
I got my first ever mint julep, pictured below in front of the racetrack. I'd been told that you either love them or you hate them. I took a sip and realized, yup, I'm on Team Julep.
The clubhouse area was nice and, best of all, dry, but I was getting antsy and feeling a bit self-conscious the longer I wandered around alone. I seemed to be the only person without a group and I was definitely the only spectator wearing a backpack.
Plus, though I was surrounded by all this glitz and glam in the clubhouse, that isn't how the majority of the 150,000-plus spectators do the Derby. I set out to find friends of a friend I had coordinated with earlier in the week who had infield tickets. These are considered the general admission tickets and are the cheapest option, costing $70 apiece. About 80,000 spectators pack the infield each year.
At this point, it was around 3:00 p.m. and pouring rain. The racetrack had reached peak rowdiness with everyone shoulder-to-shoulder under the covered areas. I couldn't have found my best friend had I lost her in the sea of people, but miraculously, a group of people I'd never met before found me.
The pack included a couple of University of Louisville alums and, for some, it was their 10th derby. It's common for students to go — campus is less than a mile away — but they've been coming back ever since graduating in 2012. Two members of the group flew in from Denver and one road-tripped in an RV from Detroit.
They asked multiple times, while glancing at my three-inch heels, if I was sure I want to go with them to the infield. I wanted the full Derby experience. Plus, whatever was waiting for us in the infield had to be better than continuing to wander Churchill Downs as a party of one, so we headed in.
You enter the infield through a tunnel, which had been temporarily closed a few minutes before, due to flooding:
The infield was a completely different scene. It was one massive outdoor party. A live band played under this Vineyard Vines tent.
The puddles were intense.
And the attire was different. There were fewer heels and pastels, and more cowboy boots and ponchos. I traded in my fascinator for a more weather-appropriate hat.
You don't have a view of the racetrack or a seat, but there was a big screen showing the races. Most people in the infield, I learned, aren't there to watch the actual races, though. "I've never even seen a horse at the Derby," said one woman, who has bought infield tickets the past three years.
We were already soaked, but after a few hours in the infield, we were also shivering and caked with mud. I was told, multiple times, that "this is the worst Derby" and "it's never rained like this," but no one really seemed to mind the weather.
With the main event approaching, we had a choice to make: Watch the "greatest two minutes in sports" in front of a small, outdoor TV with tens of thousands of drenched and inebriated spectators or on a big screen from the comfort of a warm home. My new friends went to school with Louisville natives and had been invited to a friend's parents' Derby party close by.
We took the second option, raced to a country club neighborhood about 10 miles from Churchill Downs and arrived just in time to see Justify win the red roses.
The homeowners, whom I'd also never met before, offered warm towels, a shower, homemade chicken noodle soup and a Charcuterie board that could be in Southern Living. It was southern hospitality at its finest.
Over the course of my 12-hour day, I went from the ritzy box seats of Churchill Downs, sipping a mint julep alone, to the rowdy frat-party-esque scene on the infield with a dress so drenched it was, as my dry cleaner put it, "unsalvageable," and ended up surrounded by 15 strangers-turned-friends in a beautiful home.
Having experienced two very different sides of the Derby, I realized you don't need to spend thousands to have a good time — all you need is a $70 infield ticket and a good group of people.
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