Here in Louisville, Kentucky, around the same time that folks start filling out basketball brackets, ladies start shopping for the perfect Derby hat. Everyone knows that you get your hat first and THEN the dress! That’s a Derby fashion tip. Want others? Our Research TravelingMom shares her unofficial Guide to the Kentucky Derby for anyone thinking of attending the fastest two minutes in sports!

An Insider's Guide to the Kentucky Derby

The Fastest 2 minutest in sports is a culmination of months of build up to this moment. Photo Courtney: Wikipedia Commons

If your bucket list includes a trip to Kentucky to see the running of the Kentucky Derby, you are in luck, because I can share some insider information with you!

First up there is some pretty important lingo for you to learn before a visit for the Derby, and I don’t just mean things like trifecta and exactas! So we’re off –


The Insider’s Guide to the Kentucky Derby:

Derby Day

So this is a pretty straightforward phrase but I am throwing it in just in case you aren’t totally up to speed on the Derby. The Derby happens the first Saturday in May and has for 144 runnings of the historic race. Derby day is traditionally the day that all of the celebrities descend upon the track to watch the race.

However, it is a joke in Louisville that we take 2 weeks off to party for a 2 minute horse race. This is closer to the truth than some folks would like to admit. The Kentucky Derby celebration is kicked off 2 weeks prior to the big day with one of the country’s largest fireworks display called Thunder Over Louisville. With an air show in the hours leading up to the fireworks, thunder goers camp out starting early the day of (and some even the night before) to get a good spot to enjoy the festivities.

Oaks Day

This is the Friday before Derby day and has always been called Louisville’s day at the Downs (because the race takes place at Churchill Downs, in case I hadn’t mentioned that before). For years this has been the preferred day for the locals to head out to the track and bet on the ponies.  Be sure to try the Oaks Lilly, the official drink of the Oaks. It is my all time favorite cocktail to purchase when we are visiting Churchill downs.

However, recently this has shifted, which brings me to…


Now, I really shouldn’t be telling ya’ll about Thurby because you aren’t local but I am going to make an exception if we can keep it between us! Thurby has become trendy pretty recently, as in in the last two years or so. Mainly because the Oaks have been increasingly popular and thus more and more crowded. There has always been a standing joke (that really isn’t a joke) that no one in town works the week of Derby because it is a week long celebration. It is truly trending that way. Thurby – Thursday of Derby week for you visitors – has recently started taking the place of Oaks day for the locals. We’ll let you come but only if you don’t tell everyone!

People still dress to the nines and make sure that their hats are on point, but they are able to have a little more elbow and breathing room if you know what I mean!

The Infield

The infield is an area in the middle of the track where party goers (and college kids) tend to flock. The infield is an ok spot as long as you don’t mind being in the midst of a wild, giant party. Think porta potty surfing and sliding in the mud.

So now that you know what’s what in terms of the Derby, I have some more things to share with you in terms of what to expect.

It is Crowded

I know that the first thing you thought when you saw that was “duh, Allison.” But no, really, it is uber crowded. For a point of reference last year there were 170 thousand people in attendance. While that doesn’t seem like a huge number you need to keep in mind that Churchill Downs isn’t a huge place. You become very acquainted with your neighbor. Elbow to elbow type of acquainted, wear extra deodorant acquainted.

Be Prepared to Wait

There is a lot of waiting. In line to bet, in line for a drink. Most surprisingly I wasn’t aware of the length of time between the actual races. The first time I went to Churchill Downs I placed my bet on the horse that I picked to win the first race, which by the way came in last. Then I eagerly re-positioned myself in my seat, looked over the racing program, placed my bet and waited. Turns out that there is typically 30 mins or longer between races. So while the races themselves are fast paced, the time in between doesn’t seem to go very quickly. The upside is that there is plenty of time to carefully make a decisions on which horse to bet on, refill your mint julep and freshen up in the bathroom.

Go All Out with Your Fashion!

The Kentucky Derby (and the days leading up to the Derby like Oaks and Thurby) is an excuse for you to go wild with your fashion choices. Want to wear the biggest hat that you can find? Go for it! Your date wants to wear his seersucker suit? Game on! The wackier fashion the greater the chance you will see yourself featured on the evening news.

At the end of the day no matter which event you end up attending, having fun is the most important part! Have you been to Derby?

Headed to Louisville but not sure what to do while you are in town? We have you covered with our list of 41 Free things to do! Maybe you are just wanting the scoop on the famed Mint Julep, we’ve covered that too!

An Insider's Guide to the Kentucky Derby. All you need to know and all you never knew you needed to know!