Talk Derby To Me: Our Day At The 2019 Kentucky Derby

Tickets secured early? Check.

Fascinators? Check.

Advice for infield seating? Check.

Review of prohibited and allowed items? Check.

This anxious person’s checking and rechecking of these items and more over and over? Check.

The Kentucky Derby is a very exciting and highly anticipated day out, but when you struggle with anxiety like I do, these days can be fraught with decisions, second guessing, wondering and worrying. It was like that for me until 8:30am on race day. That’s when we entered Churchill Downs and there was nothing more we needed to do or not do.

Tickets

We signed up for the Kentucky Derby emails to make sure we didn’t miss our chance to get tickets since we only plan on doing each state once in our 5 year, 50 state road trip. Well, except for Vermont.

You know our budget woes (and whoas), so we were only looking to get infield tickets for the Kentucky Derby. We paid $65 per ticket which included whatever fees get added. If we’d wanted a seat – even the cheapest – we were looking at paying $320 per ticket or more. We therefore opted to, you know, eat, drink and have accommodation for 6 days on our road trip instead of blowing it on the “cheap seats”.

If you purchase seats, you can get a parking pass included at the KY Fair and Expo Center and you’ll be shuttled to/from Churchill Downs grounds.

Parking

We researched parking options and chose to park at Cardinal Stadium which is less than a mile from Churchill Downs. Parking there cost $20 and while it said on the website that parking opened on the day at 7:15am, we found that it didn’t really open until ~7:30am. As there were 4 of us, the parking fee was reasonable for the 12+ hours we anticipated needing it for.

There are those who choose to park in the surrounding neighborhoods, either by paying homeowners for parking or finding free street parking.

Our parking worked very well for the day until it was time to leave – more on that later.

Security

Before entering the infield, you have to go through security. And they’re not playing. They give TSA a run for their money for sure.

Check out the allowed and prohibited items before you go. It’s so important. Several people had items confiscated or were turned away to take things back to their car for not reading the rules properly. I was very stressed about this process. I was so worried we’d do the wrong thing and be turned back after all the work to get up and out of our hotel early.

Thankfully, we followed the letter of the law and were permitted entrance after every inch of our bags, blanket, coats and chairs were searched.

Once you’re in though, you’re in. Your tickets only work once, so you can’t leave and return.

Entering The Infield

The gates for the infield open at 8am.

The first race isn’t until 10:30am and the Kentucky Derby itself isn’t until 6:45pm. This can make for a very long day. Thankfully, we were aware of this by the time the day came, so we were well stocked and prepared for a full day of fun and racing.

You’re allowed to bring blankets and chairs in to the infield. Part of the fun (read *stress* for me) is choosing just the right spot to see the races. Many people line up before 8am so they can run through and claim their spot – like the land races of old.

We all lined up and rushed to find the right spot, staking our claim with people, blankets, chairs and tarps. Barry, from the Barn and Backside Tour, had suggested getting a spot along the fence so you can see the turf races that happen throughout the day which is closer to the fence line than the dirt track the Kentucky Derby is run on.

It’s well known that there’s a party atmosphere in general in the infield, but no more so than in the “college area”. This is where college-aged young people party harder than most (I say most because we saw some pretty hardcore partiers on the other side – more on that later). We debated between one end and the other, but the ‘other’ put us much closer to college party town, so we opted for the far end.

In the image below, we placed ourselves at the blue X and college party town was at the red X

As it turns out, other than not seeing the very start and finish of the Kentucky Derby, we had a perfect spot. Not only were we near good bathrooms, a fun bar area and easy wagering, we had the best neighbors! On one side was a mother-daughter pair from Canada who were celebrating mom’s birthday. On the other was a group of 5 or 6 men who’d come down from Kansas City to experience the Derby (Hi Prentice, Charles and everyone else!). We all banded together, watched each other’s things, shared snacks and it made our day even more fun.

I know that you read the paragraph above and thought… you’re there for the Kentucky Derby and didn’t position yourself for the start or finish? Stephen did advocate for that, but even by the time we got in it was getting really busy at that end. Plus, I was playing the long game. We were there for 12 hours and the Kentucky Derby really is just 2 minutes of it. I think if we were that worried about seeing the start and finish we should’ve gotten raised seats. We had a huge board to watch all the races on and ended up having a great day.

Drinks

The drink of the Kentucky Derby is the Mint Julep. It’s basically simple syrup, mint leaves, bourbon and water. I didn’t particularly care for it, but after a few sips I started to be less startled by the flavor.

I did find ‘my drink’ though. I’m now convinced that I should’ve gone to The Oaks the day before. That’s where the 3 year old fillies run (the Kentucky Derby is colts and fillies but since only 3 fillies have won in 145 years, they don’t compete often) and the theme of the day is pink. Right down to the signature cocktail for The Oaks, The Lily. I can’t tell you exactly what was in the Lily, but I can tell you it was made of love, joy, sunshine and rainbows and you should drink it at any and every occasion. In fact, it was so good that I wasn’t worthy enough to take a photo of it.

I also tried the Woodford Reserve Spire which was good. A shot of Woodford Reserve, lemonade and cranberry juice. This was good, and the bartender tried to convince me that it should be my drink of the day, but alas, the Lily had captured my heart… and all my money.

Drinks are $15 a piece, unless you slum it with beer at $12 a can. In the end I had 1 Mint Julep, 2 Lilies and 1 Woodford Reserve Spire. It’s definitely tough, especially when you’re on a budget. Days like this are made to be enjoyed – not to be plastered. But at $15 a drink it was hard to even feel good about a cocktail or two. But I followed Stephen’s lead (the budget master) on how many we could afford for me to enjoy.

One drink that’s not $15 is the limited edition Mint Julep. For the 2019 Kentucky Derby they were $1,000-$2,500 and that goes to charity. The rest of the Mint Juleps on offer are premixed, but you do get a fun commemorative glass.

Tip from our favorite bar girls – if you want the glass, wait until the end of the day. They break very easily, so it’s best to save that until your last drink if you only want to have one and keep the glass safe.

Charity

Speaking of charity, there’s a 50/50 raffle you can enter throughout the day. I only entered once for $5, but if you win you split the ticket sales 50/50 with the Churchill Downs Foundation. Sadly, I didn’t win, which isn’t surprising since I only entered once, but it’s a day of taking risks for big rewards right? The winner split almost $80,000 with the charity.

Churchill Downs Side

You can leave the infield throughout the day and we did this twice. Not to head outside the grounds (as mentioned above, once you’re in you’re in), but to check out the areas of Churchill Downs outside the infield. There’s a tunnel you take which you enter under the EXIT sign. This feels confusing – especially after a mint julep or two – but you’re only exiting the infield, rather than Churchill Downs itself.

On the Churchill Downs side there are a few more gift shops. This includes the official shop attached to the museum; if you’re looking for something like a little horse statue, that’s the place to go.

The horse stables for before each race are also there…

…there are photo ops with great backgrounds (although we had some fun photo ops on our side too!)…

…and…

…all…

…the…

…hats.

I *highly* recommend going over early in the day. We headed over pretty early on – around 9am – and were able to have a nice look around without the crowds that you find later on.

We went back later as well to see some of the horses lined up before a race but it was so crowded it was nearly impossible to get close. Word on the street is that you get much better views on Oaks day, another reason besides the Lily to come on the day before the Kentucky Derby.

I mentioned the partying earlier. There’s a lot of partying on the Churchill Downs side, just fancier. Lots of champagne and cocktails flowing. Also, a lot of heels. One woman in particular fell over right in front of us. She was clearly wasted (and it was only 1pm, so still pretty early in the day) and literally just fell over. Didn’t trip or anything. Just fell out. She was OK, just embarrassed and dazed. She kept looking at her feet like they’d betrayed her, but I think she was trying to figure out whose feet they really were.

Mom collected her hat and some other girls collected her drink while her man collected her. The girls walking away made a comment about how “she needs to get herself together since she was at least 60”. Yes, the partying happens at all ages at the Kentucky Derby. But no one likes a sloppy partier. So enjoy your drinks responsibly or you might end up the conversation of someone’s blog and the butt of some young woman’s jokes.

The Churchill Downs side is also the only area where you can get the Oaks Lily and Kentucky Derby Mint Julep commemorative glasses, so if you want either of those you need to make the trip through the tunnel at least once.

Wagering

A note about wagering. In addition to strong feelings about horse racing, the other reason people might be opposed to the Kentucky Derby is the gambling.

Personally, we love Las Vegas. We occasionally buy lottery tickets. We’ve been to see turtle racing and we’ve bet on hermit crab racing in Jamaica. However, we work together and we know our limits. We set aside the “fun money” ahead of time for this and we are perfectly OK to lose it all (another reason we didn’t pay $320 per seat, so we had a little fun money in the budget). That’s it. When it’s gone, it’s gone.

There are 14 races on the day. The Kentucky Derby is race 12. You can bet on all of them – either in person or using the Churchill Downs app. Frankly, what fun is an app!? We went in person to basically the same lady all day and she was wonderful. She was very kind and explained a few things to us when we first arrived. You need to get the Kentucky Derby program which costs $5 (and is worth it) so you can see all the races and the horses running them.

We gave ourselves $6 each per race to wager on the horses throughout the day. That’s $2 to choose one horse to Win, Place or Show (1st, 2nd or 3rd place). I used the very scientific method of checking the program and going with the name that stuck out to me. Sometimes I used the “Ouija Board” method (I let the pen guide me to a name) or occasionally I bet on the long odds for fun – except when it really mattered… more on that later.

Be prepared to bring cash. We had credit cards ready to use for drinks when possible, but overall we used cash all day and you need it for wagering unless you’re going to use the app. There are ATMs around but they apparently run out of money at times, so if you wait to get cash on site you need to get it early.

To wager, you walk up to the window. You state the track (race) number, the wager amount, the type of wager – we went ‘Win, Place, Show’ all day (otherwise known as “Across The Boards”) – and the horse number you want to wager on. If they tell you a horse is scratched from a race, you have to choose another horse. This can be very stressful when you’re using less scientific methods than I did.

By the end of the day we were pros… on that one type of wagering. We tried to participate in the Bourbon Double which was picking the right horse to win in both the major turf race of the day (Race 11) and the Kentucky Derby (Race 12) but we ended up having to go to several places because no one seemed to know what it was. And we’re still not really sure if we bet on the right thing.

Again, this was all in good fun so we didn’t lose any real money. Well, I mean, it wasn’t monopoly money but we didn’t lose a large portion of the millions of dollars that was lost by those that wagered on Maximum Security. In the end, we wagered $133 and won $47.80.

Food

With all this walking around, drinking and wagering, you’ll need sustenance. You can buy food or bring it in. There are strict rules about food being brought in, so check the prohibited list for the bag sizes and amounts available for each member of your party before you attend.

We brought homemade wraps, chips, salad, fruit and protein bars. And one of us, *cough Stephen* brought an entire 32 bottle case of sealed, unopened water. Had it been a hot day, that might’ve been a good choice. By the time we left, we’d not even drank half and so he hauled it all the way back to the car.

Weather

Because it wasn’t sunny and it was cool, we were chilly a lot of the day in our sundresses and polo shirts. I brought a hoodie, mom had a light sweater and my stepdad had a rain coat. We all had ponchos. Mom and Steve bought additional ponchos as we started to get really wet and cold.

Dress for the weather. The infield really doesn’t have a dress code. You’ll see fishing waders, those dressed to the nines in 6″ heels and everything in between. Wear what works for you.

I chose a nice dress that I could be comfy in all day, a fascinator and my comfortable hiking sandals. Stephen wore a polo shirt, shorts and hiking boots. Mom brought better sandals for walking to the car later, but wore her pretty flat sandals for the day. Steve wore tennis shoes. You. Do. You.

There were a lot of rain boots with fancy Derby hats, suits and dresses. Make sure you’ll be warm enough and dry enough. Many folks brought tarps too but you can only put them up so high. Umbrellas aren’t allowed no matter the weather so that people’s views aren’t blocked. If it’s a sunny day, bring plenty of water and wear your sunblock.

The Kentucky Derby

Finally, it was time. The race of the year! The 145th running of the Kentucky Derby. I had my last Lily of the day ready, my wagers were in and the horses were heading to the post.

If you follow horse racing at all, then you know that Omaha Beach was the favorite and the favored jockey of the year (who won on Justify last year), Mike Smith, was due to ride him. Three days before the Derby, Omaha Beach was pulled for a problem with his epiglottis. My understanding from one article I read right after Omaha Beach pulled out said that Maximum Security’s trainer, Jason Servis, decided to stay with his jockey Luis Saez rather than replace him with Mike Smith once Omaha Beach was ruled out – something he may be really regretting now.

I bet on Improbable. I loved the idea of his name. And he didn’t have terrible odds. In retrospect, I have no idea why we didn’t just put $2 on each horse for the Derby to win or at least why we also didn’t just place a wager on the long shot Country House to win as his odds were 65-1.

When we were staying in London KY, Stephen got chatting to a guy at the movie theater who gave him a tip that he should bet on Maximum Security. With no horse racing knowledge, he figured that was as good a reason as any and so he bet $2 on Maximum Security to Win, Place, Show.

One great thing about the Churchill Downs track, and infield, is the GIANT screen. It’s the size of 3 NBA courts. It can be seen from everywhere.

So we heard the bugler. We sang ‘My Ole Kentucky Home’. And we watched all the horses line up at the post (positions were chosen on the Tuesday before by random draw). Improbable looked spunky and was led to post 5, Maximum Security to post 7.

Once everyone was in they were off!

We watched the screen until they were in front of us.

We cheered and jumped up and down!

We turned back to the screen.

The crowd roared as the horses came to the last turn heading down the straight.

Here’s a video Stephen took of the action:

Maximum Security …. WON!!!

So much cheering and celebrating!

Until… a race announcement came over that two racer objections had been filed about the winner. All tickets were to be held.

After *much* deliberation – like 25 minutes worth – the result came back. Maximum Security was disqualified from the Kentucky Derby for impeding War of Will and therefore Country House during the final turn by leaving his racing line. He kicked War of Will several times when you watch the slow motion and War of Will is pushed into other horses in the pack.

That meant Country House won the 145th running of the Kentucky Derby.

I’ve never heard so much booing in my life – and I’m a Redskins and Mets fan (talk about supporting the improbable). The news really didn’t pick up the vibe and volume of the everyone’s discontent at Churchill Downs over the stewards’ unanimous decision.

The result meant that 6.5 million dollars in wagers were lost at Churchill Downs. And approximately $250,000 were won by those who bet on the 65-1 long shot Country House. Outside of the race track, it’s estimated that 42 million dollars overall were lost on Maximum Security wagers.

End Of The Day

At the start of the day, we’d planned to stay for the final two races after the Kentucky Derby itself so that we could avoid parking nightmares. The rain was so heavy in the end that we decided to head out after the Derby, but we took our time. Almost everyone tries to leave at the end of race 12. So if it’s a nice day then just sit, enjoy your sunshine, and relax to avoid the mayhem.

We made our way out the front gates of Churchill Downs because at least they were moving – the tunnel we arrived in to the infield earlier in the day was at a complete standstill. The lines for taxis and shuttles were unbelievable and we were so proud of ourselves for our forethought in walking the half mile to the stadium.

That’s until it was over an hour after we’d been in our car and hadn’t moved an inch. We heard the next morning how awesome the Louisville police did in managing the traffic because usually it’s horrendous. We laughed, knowing that we encountered the less adept traffic managers and as a result were starving and exhausted by the time we finally made headway.

We finally saw that people were leaving out of a separate entrance and we made our way over. At this point everyone was frustrated so people were being reckless. Stephen was alert and did a great job. The officer at another intersection was very upset and on her radio, so it was obvious that something wasn’t going to plan further along the road. We finally got moving, only to sit at yet another intersection, where there was an officer in the middle only allowing one direction of traffic through, meaning all three other directions sat there forever.

That, other than the drink prices, was our only downside to the entire day. They seem to have sorted issues with shuttles to/from Churchill Downs, but still haven’t worked out all the other roadway challenges for those of us leaving Cardinal Stadium.

Final Thoughts

I think that about wraps up our day at The Kentucky Derby. It was historic, memorable, rainy, hilarious, expensive and a ton of fun.

Would I do it again? Absolutely. But honestly, I think I’d try The Oaks before I’d do The Kentucky Derby again.

I’ve learned so much about horses, racing and more since being in Kentucky and for that education I’m grateful. I said in my previous post that I felt confident about the treatment I saw (with my own eyes) horses receiving. And I still feel that way.

But I’m also aware that there’s a dark side to horse racing and it shouldn’t be ignored. Here’s an article that offers some solutions to help regulate the horse racing industry.

We had the opportunity to visit Old Friends Farm – a racing horse retirement farm – the other day and that was a beautiful place full of horses loving life and living as horses should.

I will say that between now and my next Kentucky Derby, I need to teach a lot more Outschool classes because I’m gonna need a covered seat and that $1,000 dollar Mint Julep!