Posted in Holidays, Tuesday Talk

Tuesday Talk: All About the Oaks


Last week I mentioned that the first week in May is a busy and festive week around here.

I recently shared my Keeneland post, and today I’m sharing all about the Oaks.

Oaks is the day before the Kentucky Derby. Like Derby Day, there are races all day long, but the main race, the Kentucky Oaks, is for three year old fillies (girl horses).

For Oaks, many wear pink in honor of the breast cancer survivors who walk in the parade before the Oaks race. It’s such a powerful moment to see so many survivors walking together.

If I don’t find a pink dress, I will add a touch of pink with a fascinator. Years ago, if we went to Oaks or Derby, I’d usually wear a fancy hat, but I much prefer a fascinator.

My dress is from Nordstrom, and Amazon for the win for my pink fascinator. (I’d ordered a couple of them and also borrowed a couple from a friend, but Hadley helped me make the final decision)

Travis was already in Louisville, so once I dropped the kids off at school, I headed to pick him up.

I got to Louisville around 11:30, and we were at Churchill Downs by 12:00.

Upon arrival, I was handed the signature drink, the Lily, which was the perfect way to start the day.

For the second year in a row, the ticket was all- inclusive. So, any food or drink is included in the ticket price. Of course, there were still lines for food, but they moved pretty quickly considering the crowd. Also, there were fridges throughout with drinks like water and soda that you could just pick up as needed.

After the first few races, we headed to the paddock to check on one of Trav’s client’s horses who was running.

You have to be a horse owner to get into the paddock, and even then, the pass is for the specific race for your horse. The filly we were there to see was Kneesnhips. Any guesses what the owner does for a living? Then, we headed back to our seats to watch the race (and it was raining just a bit then). She placed 4th.

We stayed in our seats for a bit, but it was only a steady rain for about an hour.

Our seats were in a box (of 6, with friends) that was undercover right near the finish line which is always so fun.

Oaks and Derby make for great people watching, and we always run in to people we know. They said the attendance was at 100,000…and I believe it!

Of course, there are usually more celebrities for Derby, but Kirk Herbstreit (sports analyst) sat right behind us. Then, as we left, I saw Justin Harley (This is Us) walking out with his wife. He did the “riders up” in the paddock before the big Oaks race.

You may remember from my post on Friday, but I was very concerned about the weather. Friday’s weather actually turned out better that Saturday’s weather for Derby. It really just rained from about 3:00-4:00, and then again around 6:15 when we got in the car.


So, for years, Oaks was more for the “locals” (Louisville people) and the Derby was when so many from out of town would come. Quite a few years ago, they started having “Thurby” which is now when most local people go.

Travis and many of his Louisville friends now go for Thurby. Honestly, Oaks and Derby are big work days for him now, so Thurby is a bit more relaxed for him.


With a post about Keeneland and now Oaks, it would probably be natural to have a dedicated Derby post. That being said, I haven’t been to Derby in years. Travis had a streak of almost twenty years of going to Derby. That streak came to a halt once we had kids (haha) who usually have activities that day. Plus, Thurby and Oaks are enough. I’m not saying we won’t ever get back to Derby, but he really does a lot for work that entire week, and now has the tradition of watching all the Derby day races on at home while also placing bets and working. It varies year to year, but sometimes we get together with friends. The weather was cooler and rainy this year, so we just hung at home.

My mom actually hosts a Derby party (in KC) every year that I know her friends look forward to each year.

Let me tell you the one person who doesn’t love a long shot–Travis. The horses that placed 2nd and 4th were connected to his farm. While those are pretty good finishes, Epicenter (who placed 2nd) was one of the heavy favorites. Like much of the world, Travis was speechless to see Rich Strike, with 80-1 odds, win.

A Few Derby Facts:

  • Derby is always the first Saturday in May.
  • The horses that run the race are all three-year-old colts.
  • There are 20 horses in the Derby race.
  • The Mint Julep is the signature cocktail.
  • It’s called “run for the roses.”
  • It’s the “most exciting two minutes in sports.”

One thing I wish Lexington would do that Louisville does is there’s no school on Oaks Friday. The city basically shuts down and traffic is probably extra crazy which is why that’s more of a necessity in Louisville than Lex, but it would still be so nice to have that day off.

I never realized until my kids were in school how much the schools (especially elementary) incorporate the Derby into learning and activities at school.

Schools in our district display their “Derby silks.”

There are fun Derby activities like hat making and…

jockey silk coloring.

Most of the elementary schools have activities like Derby races for the kids, learning about horses and jockeys, reading horse books, and more. One year, my kids’ teachers hosted a Derby breakfast at school.

Like most things, it’s fun to see the excitement of the week through a child’s eyes.

It really is a special time of the year. We had a great day. Let me know if you have any questions!

6 thoughts on “Tuesday Talk: All About the Oaks

  1. Great post! I was thinking about how lucky you got with the weather! I love the Lily but not the Mint Julep. I love fascinators! I love pink and green together. I want to go to Werby next year. That would be an easier day to take off!


  2. I was thinking of you this weekend when I watched the Derby. I was cheering for Crown Pride. It was a very exciting 2 minutes! Thanks for sharing your photos of what it’s like for the guests. Neat you saw Kevin from This Is Us!

    Liked by 1 person

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