Bucket List Trip

So, freshly back from a trip of a lifetime to the Kentucky Derby!

I didn’t want to mention it before, lest I jinx it. It all started at Elise’s Birthday Dinner at Kelley’s where someone mentioned the Kentucky Derby and my Mom said it was on her Bucket List and we all agreed. Kelley said she had a client in Louisville that she would e-mail to see if he could help her get tickets. Fingers crossed.

Here's where it all started.

Kelley’s client said he would find a way to make this trip happen for my eighty-something year old Mom (it was a Mother’s Day present to her), so we were hopeful, but after that email, dead silence for a while. Unbeknownst to us, the person in charge of getting the tickets had two friends killed in a bank shooting in Louisville, so he was obviously otherwise occupied. Still, he assured us it would happen, so Elise and I booked flights (Spirit) and hotel rooms at a Days Inn by the airport. The best Elise could say about the hotel was: “The reviews aren’t too bad.”

I’d wanted to stay at the Brown Hotel, where the Hot Brown Sandwich and Derby Pie were invented, but obviously, it was all booked up. It’s a beautiful, historic hotel in Downtown Louisville where Zeke and I had stayed during Covid and it was reasonably priced, at the time. But a month before the event, it was slim pickin’s. Some people had been planning their trip to the Kentucky Derby for years, as it’s on the Top Ten Sports Bucket List Trips.

As the week before the Derby approached, we still didn’t have our tickets, but we all had our hats and outfits picked out. My Mom shipped our hats to the hotel and I began to pack. Finally on Thursday, the day before we left, our tickets arrived, via text, for seats in the Clubhouse. My Mom had thought we’d be in the cheap seats in the infield, but now she said “We’ll be with the rich and famous.”

Our flight was early out of Fort Lauderdale on Spirit. Elise’s friend, who only flies First Class said: “I’ll pray for you” when she found out we were on Spirit. LOL. Our flight was delayed, but we eventually arrived in Louisville and the airport was bustling. A large fleet of private planes lined the runway at Mohammed Ali International Airport and ladies in dresses and hats handed out Bourbon Balls as a Bluegrass Band played. There was even a place to take your photo in front of a race horse statue and scads of red roses, in vases, lined the airport halls.

Dinner that night was at The Eagle, a fun and funky place that specialized in Fried Chicken. The Kentucky Oaks, the horse race with fillies, was that day and there were a lot of people still dressed in their outfits and hats dining at the restaurant. We all got lemonade, the Fried Chicken and Salads (it’s all about balance); it was all delicious. My favorite part was the Biscuits we ordered as an appetizer, that came with butter and delicious Blackberry Jam.

The restaurant was located in The Highlands, a fancy part of Louisville where they held a big party that night called Unbridled Eve. Our Uber driver asked us if we were going to the Derby and gave us some tips. His number one tip was to wear comfortable shoes. When we returned to our hotel rooms, we studied the racing sheets to pick our horses. Kelley tried on her 4-inch heels and walked around in them. “They’re not too bad,” she said. Not too bad walking a couple steps in the hotel room is different than the hike we eventually had to travel to make it to our seats.

I woke up on Derby Day to find out my Mom’s pick- Forte– had scratched from the race, due to an injury. This changed all the odds. A lot of horses, unfortunately, had died in the run up to the race and one trainer had been banned from participating in this year’s Derby, leading to lots of last minute entries. I was unsure of which horse to pick, but was strictly going by the names I liked- Two Phils, Hit Show & Reincarnate. I also recently finished a book (Hollywood Park) that said “Favorites never win,” so I had no desire to pick the favorite.

We Ubered to the area where you walk to Churchill Downs and then there was a LONG walk, over a bridge and through preaching evangelists with megaphones, to get to the entrance. Kelley was starting to crumble with her shoes and lost a bottom to one of them. We finally arrived around noon, had someone take our photo while we were semi-fresh and proceeded on to the Clubhouse entry. In a happy coincidence, Herbert Britto was the artist for the 149th Kentucky Derby. Anyone from Miami is familiar with Britto and his colorful, happy designs.

As I walked in, there was a gentleman handing out freshly made Mint Juleps with chipped ice and mint sprigs.

“Are these free?” I asked.

“Yes m’aam,” he said. “Everything inside is free.”

Wowsa! What can I say? I tipped him and entered the hallowed ground of Churchill Downs.

The Kentucky Derby lived up to the hype. The fashion! The hats! The history! The excitement! The happiness of everyone gathered there. The collective energy. It was the best people-watching I’ve every experienced in my life, without a doubt. The outfits and hats- on girls and guys- were amazing, one better than the other. I could’ve gone around all day, just gazing at the spectacle, but some of us were anxious to get to our seats.

Our seats in the Clubhouse were great- right near the finish line (kind of like being on the 50-yard line for a football game). Kelley and my Mom, feet hurting, were happy staying where they were. Elise and I went to get lunch. We all wanted hotdogs, so we waited in line and got them.

The food in the Clubhouse, while free, was like what you’d get at a football game- hot dogs, hamburgers, pizza, nachos, chicken fingers, B-B-Q pork sandwiches and the like. I tried to see if there was a favorite item going by, but there really wasn’t; it was like the predictions for the winning horses- all over the place. There was also popcorn that looked good that I never located. The hot dogs were your basic boiled hot dogs, but they hit the spot. We also got an order of chicken fingers and waffle fries later in the day that were pretty good.

Elise wanted to go see the horses in the Paddock, so I went with her, but as she made her way in, I told her it seemed everyone going in had a pass. As she waited to watch the horses from outside the paddock, I went to the gift shop. I returned with my purchases and a gentleman came out and said “It’s your lucky day” and handed out passes to get into the paddock. I gave mine to Elise, as she’d been waiting and is crazy about horses. She got to see the horses parade by a couple times, then they walked by with their light-as-a-feather jockeys atop them. She even got to go out on the field to watch the race. She waved to us from the field. She was in heaven!

Meanwhile, Mom and Kelley were busy betting, as there are races throughout the day. My Mom, whose Dad was a horse trainer and grew up on race tracks, taught Kelley how to bet. I made three bets on three different horses in the Derby to win and got myself dessert- a strawberry, banana, brownie skewer covered in chocolate. As I waited to get a drink (I wanted a Lily) an older guy in front of me said “Nice hat”, which I think must be the biggest pick-up line at the Derby. He asked me who I liked for the race. I told him I really didn’t know and he said “Bet on number 8. That’s a good horse.”

Which was how I ended up ditching the drink line and waiting in line to bet $10 on #8, Mage. Kelley had surrendered to the inevitable and bought flip flops at the gift shop. When she returned, my Mom quietly said that she needed some too, so Elise went to get two pairs of flip flops. Her smalls were too big, so when she went to return them, I asked her to get me some too. Which is how we all ended up wearing flip flops at the Kentucky Derby.

As the final race approached- “the most exciting two minutes in sports”- more and more people filtered into the Clubhouse and the excitement and energy was papable. Cutie Patrick Mahomes called for “Riders Up!”, Navy men in white uniforms ushered out the garland of roses for the winning horse and the University of Louisville Marching Band played “My Old Kentucky Home”.

“And they’re off!” We cheered & screamed like crazy while watching the magnificent creatures with jockeys in colorful silks speed by the track in front of us and then… it was over. Two minutes goes by fast when you’re having fun.

Mage ended up winning, with Two Phils second and Angel of Empire (Elise’s pick) coming in third. Tapit Trice– my Mom’s pick and one of the favorites, finished second from the bottom. I went to cash in my ticket, thinking I’d won about $30 and I could hardly believe it when I saw $157 ring up on the register! The man paying out at my window was blase about my winnings, understandably, as I watched a guy next to me collect a large stack of $100 bills. But, I was happy and my Mom was thrilled that someone in our tiny group of betters actually won, and on a long-shot. So thanks to the guy in line who gave me the tip.

Getting home from the Derby wasn’t easy, with 170,000 people exiting at the same time and there was a torrential downpour we narrowly avoided, but, eventually, we made it back to our hotel room. The airport the next day was nuts (it’s the busiest day of the year for that airport) and even more so, as there had been rainstorms that morning delaying all the flights. Tired and worn out, we finally made it back to Miami, with memories of the 149th Kentucky Derby that will last a lifetime.

If I ever were to return to the Kentucky Derby (and it’s still on Zeke’s Bucket List) my tips would be:

  • Wear comfortable shoes, like flip flops and carry your fancy shoes for once you enter the stands.
  • Get a driver to transport you to and from the Kentucky Derby.
  • Hit the concession and betting lines early, as they get very crowded as the day goes on.
  • If you’re drinking Mint Juleps (or anything alcoholic) pace yourself. The gates open at 10 a.m., but the Derby’s not until almost 7. We saw an over-served Derby-goer wipe out and get whisked away by the Louisville police.
  • Have fun! It’s a once-in-a-lifetime Bucket List trip.
  • Consider booking your flight home for Monday and visiting the Derby Museum (which is closed Friday and Saturday for the Oaks and the Derby). You will avoid the most crowded day of the year at the airport and all the dated merchandise is 50% off at the Museum store.
  • And maybe, just maybe, take a tip on a horse from a stranger in line for a drink. Ya never know!

Up Next: The Derby Lily

Published by gleeguilford

Born and raised in Miami, the daughter of a pilot and stay-at-home Mom, I love food in all forms. My great grandfather opened the first Italian restaurant in Miami in the 20's, The Boathouse on the Miami river. I love exploring my heritage and linking food and recipes to personal stories. I've been published in Chicken Soup for the Soul: Food and Love and wrote restaurant reviews and news as the Miami Dining Examiner for three years. I love exploring Miami's latest hot spots, hole in the walls and institutions. I'm always looking for innovative ways to use the plethora of tropical fruits and vegetables South Florida offers, especially from my own garden.

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