Alex and I have always thought about going to the Kentucky Derby. It seems so glamorous and such a bucket list trip! This year we decided to go and see for ourselves what all the fuss was about. Many hours were put into planning including the all important outfits and hats. We were able to score passes to the Barnstable Brown party, which is the event of the year in Kentucky as well as tickets for both the Kentucky Oaks and the Kentucky Derby in Millionaire’s Row- the private dining room and viewing box at Churchill Downs.
The first hurdle was actually getting to Louisville, no direct convenient flights from Southern California, we ended up having to connect in Chicago, getting delayed in bad weather and barely making our second flight. Stressful beyond belief as neither of us are familiar with the Chicago airport and we had to rush to find out gate and then stress about our luggage making the connection (what would have happened if my hats had been lost, oh the horror!)
We arrived and headed straight to our hotel, the 21C Museum Hotel in downtown Louisville. To be honest we had never been to Louisville and had no idea what to expect but man, the downtown area is a ghost town. More than half the buildings are boarded up or empty, hardly anyone walking around on a weekday- we are used to bustling big cities with vibrant downtown areas and it just felt kinda sad and dead to us. So much beautiful architecture and brick buildings just sitting empty. But our hotel was amazing and definitely lifted our spirits. The coolest, hippest most avant garde hotel in the middle of Kentucky? Modern art exhibits, interactive art, a super amazing foodie restaurant that we wanted to eat every meal in. Our room was small, but looked out over Main St and the river and was clean and nicely furnished. But no tub? No double sink? We were also seriously bummed at the fitness center and “spa” which consisted of like three machines, some dumbbells, and a steam room that was not working. Very depressing. Thankfully, we got our steps in walking all over downtown Louisville.
The first day we relaxed and explored the city a bit and then went in the afternoon to watch the famous Pegasus Parade. Alex had never seen a hometown parade before so he basically thought everyone had lost their minds, but I thought it was fun and a nice local thing to do. Unfortunately we had zero luck finding a taxi back to our hotel and walked half way there before giving up and calling an Uber. The highlight was dinner at the hotel restaurant, Proof on Main, which rivaled any urban foodie restaurant we have been to (and we have been to a lot). Every dish was perfectly executed and the cocktails were on point although heavily skewed towards bourbon drinkers (go figure).
The hotel hosted an exclusive brunch on Oaks day which was a wonderful way to kick off Derby weekend. Afterwards we headed to the Kentucky Oaks on a perfect sunny day to watch the races. The Oaks is a female cancer awareness day and everyone wears pink, it’s super appropriate as it is the day they race the fillies. We donned our pink outfits and took a tram to Churchill Downs. The place was packed and the corridors were lined with vendors selling everything and anything Derby related. We didn’t stop to browse since we had already been gifted 5 (!!!!) gift bags and I was beginning to worry how I would get everything home. We headed through the glass doors and up the escalators to the exclusive “Millionaire’s Row”. Tables are set for 8 and assigned in advance so we joined our group and made introductions. The other couples were all very nice, it’s definitely a mixed crowd.
The decor in Millionaire’s Row is definitely lacking. It reminded me of a hotel ballroom or meeting room type look and the buffet they were serving all day was about the same. Considering how expensive the tickets were, I was a bit disappointed. It was all you can eat and drink though, so we did not miss out on mint juleps and lilies. People watching was more interesting than the races although we did go out to the viewing terrace and watch several races in the afternoon including the Oaks. The racetrack is beautiful and it’s very exciting as the energy from the crowd is contagious. Heading back to the hotel we could not locate the shuttle and there were no Ubers or taxis available, but we managed to find a for hire driver who offered to chauffeur us the remainder of the weekend, thank goodness as I had not anticipated how difficult it would be to get anywhere during Derby weekend.
The driver picked us up a few hours later to head to Barnstable Brown. It is considered one of the top 10 private parties in the world and we were very curious, we had no idea what to expect. It’s at a private home in an area of Louisville known as The Highlands and considering how many parties we throw, I knew how much work it would be to pull off. There was a red carpet, several buffet stations set up, bars, and a stage and dance floor. We ate and drank and listened to the live music- Salt n Pepa, DMC, Kid Rock, Richie Sambora, Boyz II Men, and Joey Fatone. It was quite a mix of people from celebrities like Ty Burrell and Johnny Knoxville to professional athletes like our neighbor Bode Miller, and regular folks like us. It was quite fun and a much more up close and personal house party than any gala I have ever attended.
The next day was pouring rain, but we still walked around downtown a bit and were surprised consistently with the arts and culture available to Louisville as well as the urban trendiness of the people that live downtown. Sitting at a cafe and eating farm to table while served by a bartender wearing vintage and a man bun, we could have just as easily been in San Francisco or Savannah. After filling up on craft cocktails, oysters and bone marrow, we headed to the Derby in rain ponchos. The covered walkways were so packed with people trying to avoid the rain that we could barely squeeze through to head to our section. The viewing terrace was not completely covered, so most people were choosing to watch the races from the tv screens in the banquet area. Kind of silly to spend the fortune we spent on tickets just to watch it on tv like we could have done from home.
By the time we got through the parking lot to our waiting driver we were both soaked and covered in mud. It was less than ideal.
The consensus- I have now been to the Derby and crossed it off my bucket list, I don’t need to go again. That being said, I really enjoyed Louisville and would visit again just to enjoy the art and the restaurants and people.
