Planning Your Visit: The Kentucky Derby

Spring is here! If you are thinking about planning a trip or vacation to welcome the warmer weather, there’s nothing like planning a trip to enjoy the “Greatest Two Minutes in Sports!”. I’m talking about going to the Kentucky Derby!

Ari and I were fortunate enough to be able to attend last years Kentucky Derby (the 144th) and have gotten numerous questions about both the experience and how we planned our trip. So if you’re interested in heading to the Kentucky Derby anytime in the near future, keep reading for advice and tips to make your visit great!

A little background.

The Kentucky Derby (also known as the Run for the Roses) is the longest running sport in the U.S. It’s been going strong since 1875. The Derby is held on the first Saturday in May. This has been the official Kentucky Derby date since 1946. So, if planning ahead for another year, you have plenty of time to plan ahead and can accurately predict the date for the year you want to go!

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The iconic Twin Spires in the background!

It’s a full weekend event.

The actual Kentucky Derby is on Saturday, but the Kentucky Oaks race, which is also held at Churchill Down’s, is run the day before. The winner receives garland made of lilies (instead of roses) and in place of “run for the roses” the saying is “lilies for the fillies”. Spectators are encouraged to wear Pink for the Oaks race to increase awareness for Women’s health issues (such as breast and ovarian cancer).


If you haven’t been to the Kentucky Derby before, booking on your own may be a challenge. Because the race is reliably on the same weekend each year, hotels and other housing options get booked very quickly. The first year we tried to go, everything was already booked 6 months out. You could try your luck with an air b-n-b or staying further from the airport or track as alternate options. We ended up staying at the Crowne Plaza very close to the Louisville airport and it was in an ideal location.


Once your lodging is secured, you should check into getting Kentucky Derby tickets. There are several websites with advice on how to choose the best seats, the track views from that area, and what each type of ticket includes, if anything. Some tickets include food, or box seating with upgraded/padded chairs, or covered seats etc. The ticket differences are important to know. There are multiple online brokers where you can purchase official tickets.

The one thing I will mention here, is that almost all of the tickets mention something along the lines of: you can ‘move down’ but not up. I wasn’t truly sure what this meant, but after going, it makes much more sense and is actually really important.

Moving down but not up.

The way the seating is structured, the lower seats are uncovered and exposed to the elements. As you move up, or to the higher areas/seating levels, often those seating options are covered.

Let’s say, it’s a beautiful and sunny day at the track, and you have a middle-tier ticket. You are free to move down to the lower, uncovered areas to enjoy the sunshine and get a closer view of the track. However, if you are there on a rainy race day (and let me tell you 2018 was very rainy!) you will be glad you purchased a seating option that is covered. You can stay within your tier, covered and protected from the elements, and people in the tier below cannot come up to the covered area. (They of course can go to the concourse or other areas for coverage, but there are very limited track views from inside). Hence the statement, you can move down, but not up.

The other time a ‘move down but not up’ rule is important, is for refreshments and access to the restrooms. You can only go to the bars/refreshment areas on your level, or the levels below. The same goes for the restrooms. If you are planning to drink any of those famous mint juleps or pink lady’s, then this tip becomes important! Plan accordingly.

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The 2018 Kentucky Derby was the wettest on record!

How do they monitor this?

Upon heading to your seats, after showing your tickets, you will be given a wristband that is color coded. These colors alert the staff to the location of your seats, and thus the areas you have access to for refreshments or restroom facilities etc.

Louisville gets packed!

Over 150,000 people attend the Kentucky Derby each year. The increase in number of visitors would be a burden on any town, and Louisville is no different. If there is a restaurant you have been eyeing, definitely try to secure a reservation as early as possible. Some places won’t even take reservations that weekend, so be prepared to eat on the earlier side, or be patient if there is a long wait.

We found it interesting that some restaurants were only offering ‘one seating option’ for the evening and were quickly out of reservations. So plan ahead and plan to be flexible.

A fun dining option.

A great way to sample various dishes and libations from the area, is at the Taste of the Derby, which happens on the Thursday evening prior to the race. The Taste is held at the KFC Yum! Center in downtown. It includes food tastings from award winning chefs, regional wine pairings, live entertainment, etc. It’s definitely worth going if you can get a ticket. You’ll leave with a full belly, an appreciation for the various racing communities across the country, and feel good knowing that a portion of your ticket sale will be donated to hunger relief organizations and the local food bank.

Options for Friday.

If you are only interested in attending the Kentucky Derby on Saturday, but are looking for something else to do on Friday, I highly recommend visiting the local distilleries in the area. We rented a car and drove to Versailles, Lawrenceberg, and Frankfort to visit some of the famous bourbon spots in the area.

Hearing the stories and history behind the brands, the facilities, and their signature flavors made the weekend even more immersive. If there are specific distilleries you love and wish to tour, check ahead online to grab tickets and reserve your tour time slot. We were able to snag a couple of last minute tickets to some of the distilleries but several of them were already sold out. (Again, because events are held on the same weekend every year, people plan ahead as much as possible.)

Other details.

I won’t go into dress or hat details for the Kentucky Derby, as there are many other websites that cover attire and all things “Hat” related in brilliant detail, but I will encourage you to familiarize yourself with what to wear and grab a fun hat. Dressing up is a huge part of the weekend and adds to the fun, so embrace it!

Also, if you are a betting sort of person, and wish to place your bets at the betting window at the track (instead of online), take some time to familiarize yourself with how to bet and what you are asking for when you place the bet. It will make things much smoother!

We placed our Derby race bets at the betting window because it was important for us to get the full nostalgic experience of betting at the storied track windows.

Tip: Try to get your bets in (for whatever race) earlier in the day. Any time on race day, you can place your bet for the Kentucky Derby race. You might now know it, but there are horse races throughout the day on Derby day!

The final race of the day is the “Run for the Roses”. This is the Kentucky Derby Race that everyone back home will be watching on television.


An additional thought.

Sometimes planning and logistics for the race can be a headache. There are a few companies that offer packages specifically for Kentucky Derby weekend. Often these companies have longstanding contracts with local hotels and transportation services to make your Derby experience seamless.

If you are looking for something like that, they do exist! Most, however, do not include airfare to Louisville, so you are on your own for that. They will likely include seating for the Oaks and the Derby as well as transportation to and from the hotel to Churchill Downs, plus a reception, gift bag, etc. The transportation part is key, as cabs, Ubers, etc often have enormous surge pricing and traffic is congested and grid-locked. Also, if you have enjoyed a few too many libations, it’s always better to let someone else handle the driving.

One company we looked into for a package Derby experience was Prime Sport. They were a great option but there are other options as well! A quick internet search can give you more suggestions.

I hope you found this article helpful as you plan your Kentucky Derby trip for an upcoming May! If you are headed to Louisville, be sure to slow down and take in the beauty of the rolling bluegrass fields, the numerous roses, the elaborate hats, and all the fun! Cheers!

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