Monday, May 4, 2026

Kentucky Oaks in Louisville

We’d had such a good time at the Kentucky Derby last year, that we wanted to see what the Oaks was like. We’d heard it was younger people and a more casual vibe. Tickets were also cheaper – just $70 for the infield. Kate and Matt were also going, but they did the two-day package for the seats.

Last minute, Kris couldn’t go with me, so I asked my friend Rachel, and wonders of wonders – she was free! Sure, she had to keep her eye on two live video streams, one of water filling her cottage crawl space, and one of her pregnant horse who was due to give birth, but otherwise totally free!

The drive to Kentucky is really easy – just five and half hours on the highway. I drove, and Rachel and I had a wonderful time talking. The hours really flew.

When we neared the city, we were greeted by pretty stone tunnels. They were so beautiful, and Rachel in particular loved them.

We checked into the hotel Kate and Matt had gotten – the Hampton Inn and Suites Louisville East Oxmoor. The people there were so incredibly nice. They were all dressed up in finery and hats, and they were hosting a party in the lobby. They offered us free Oaks Lilys and Mint Juleps, pointed us to the pretty buffet of Kentucky Derby-themed foods, and encouraged us to hang out and listen to the live music. They also offered to take our picture in front of their Kentucky Derby backdrop, and asked us all about where we were from and what our plans for the Derby were. They were so nice and wanted us to love it in their town, which was a theme that was repeated the entire weekend.

Rachel and I enjoyed the lobby music for a little while, and then we drove downtown and picked a parking garage to park. We walked by the Cardinals stadium and checked out the Bluegrass Brewery. I asked a question about Louisville, and Rachel answered that that when you have a city that doesn’t pronounce a letter they can do whatever they want! (Side note - our GPS pronounced the town Lou-ee-vil-ee. Delightful!)

Just as we were leaving the sun was setting, so we hurried over to the river (including wearing wedges on cobblestone leading into a dark tunnel – but!) It led to a scenic view of the river and bridges. We ate dinner at the Country Boy, checked out everything that was happening downtown, and went back to the hotel to meet up with my brother Gage, Kate, and Matt. They all got to the lobby at about 11:30 p.m. and we talked to them until 1:15 a.m. It was a happy coincidence that Gage was in town – just so happened he had a flight scheduled there!

Kentucky Oaks

We woke up early and got all prettied up for the day. Rachel called our hats fancifers, and I liked that even better than the name fascinators. I wanted to get to a place where we could park in someone’s yard, and I knew that last year I’d paid $30. We drove right to Churchill Downs, and a man offered us parking in his yard - $40 and guaranteed out. Sure!

We walked to a diner named Wagner’s Pharmacy to meet Gage for breakfast, but we were on the wrong side of a fence, so we had to walk across the overpass road, cross, and walk back. This added two miles to our walk to Churchill Downs, and Rachel was very happy she had worn sandals that she could walk in instead of pretty heels.

Gage eventually was able to direct his Uber driver to the right spot, and we were pleasantly surprised by Wagner’s Pharmacy. Since it’s right next to Churchill Downs and kind of famous, I thought it would be packed and expensive. No! It was fine and affordable, too. We all talked and had a lovely breakfast complete with very Southern biscuits.

I made the same mistake I made last year and walked a long way to the wrong gate, and then back again to the correct gate. The good news was we saw a gorgeous parade of outfits along both ways!

Gage said goodbye to us just before the first race at 12:30 p.m., and we entered the infield just as it was starting!

For the rest of the day, we walked around, watched from different spots, tried to find the least windy and warmest spots, and cheered on the horses. Rachel bought a fleece blanket, and we sat on it and wrapped up in it. We participated in fake betting, where we enjoyed choosing our winners before the race, and then watching them lose – but with no money our of our pockets!

Things I love – the bugle call (what a thrill), the horses trampling past, especially when they’re on the grass, people’s outfits, THE HATS, and the happy atmosphere.

There were way fewer people than there were at the Derby, and there were younger people. One time as we were crossing the middle at the height of the day - about 3:00 p.m. - it was as if we had stumbled into a college party! All college-aged kids, all dressed in cute outfits, all loud and flirting and laughing …some even falling down, getting kicked out by the police, and others being forced to empty their pockets of airplane bottles! By the late afternoon, it had really calmed down and a lot of people left. The final race was at 8:40 p.m., and I did bet on it and lost $6. I didn’t expect to win, since I won the Derby last year, so that was a manageable amount! High stakes gambler over here. On the way out, I found a penny. That meant I only lost $5.99!

Rachel and I left and were hungry, so we stopped at a gas station on the way to the car to buy candy bars for dinner. Only the finest dining for us! 

With traffic, it took awhile to get back to the hotel, but it was fine. My watch told us we'd walked nine miles. Kate and Matt weren’t much farther behind us, and we heard about their fun day before falling asleep. 

Derby Day

I woke up early and worked in the lobby. A hotel staffer immediately offered me a mimosa. So hospitable at 6:00 a.m.! I didn’t have one, but that was kind of him to offer.

There were six men with laptops, the book from the races, pens, papers, and very angry demeanors. They were discussing the races and choosing what to gamble on. But they were not having fun. They were mad. They must not have won the day before, or perhaps they were in gambling debt, and one of them was mean to a guy who said to them, “You guys look like you know what you’re doing!” I didn’t like them, and I took notes on what they said. (Later I was able to check - they didn’t mention the winning horse once. In fact, none of the horses they mentioned were in the top three.)

But that’s horse racing. With all their knowledge and insider info and research – my guess was as good as theirs.

We ate breakfast and said goodbye. We saw the tunnel again on the way out.

“I love infrastructure!” Rachel said.

We turned back to check on her pregnant horse on video. We’ll watch them in person, we’ll watch them on the big screen, we’ll watch them on her phone. Horses are fun, and so is the whole Derby weekend - especially if you can stomach a $5.99 loss.