Travel Tuesday: The Oaks and Louisville, KY

I was fortunate enough to tag along with hubs on a work trip several weeks ago to Louisville, Kentucky! The star of the show was attending The Oaks race at Churchill Downs, but we had plenty of fun outside of horse racing. Namely, bourbon tasting.

Here’s a bit of backstory on The Oaks 2026:

The 152nd Longines Kentucky Oaks was held on Friday, May 1, 2026, at Churchill Downs, featuring a $1.5 million purse for 3-year-old fillies. Always a Runner, ridden by Jose Ortiz, won the race, which was historically held under the lights for the first time with an evening post time. The event, known as “Lilies for the Fillies,” celebrated “Pink Out” for cancer awareness.

Prior to the final race, we spent the day in a suite enjoying cocktails, snacks, and our own personal betting machine. This was my first time at Churchill Downs and I can’t believe how much fun we had placing petty bets on horses we know nothing about. The people watching is next level. The outfits are spectacular!

The Oaks Suite

The famous Lily cocktail is delicious! I much prefer it to a mint julep.

The prominent spires are pink for The Oaks.

Despite the weather being a little cooler than normal, we had the best day with this crew. I hope we get to go back next year!

The other highlight of our quick trip was a tour of the Old Forester distillery. I am not a big bourbon drinker, but that didn’t matter one iota. The tour was fascinating! Our guide, Evra, made this such a fun and informative experience. If you go, ask for her. Everything from the barrel making to the fermentation process was thoroughly explained and demonstrated. It’s wild! I even found a bourbon I like.