If you are trying to decide whether or not to take a last minute trip to the Kentucky Derby, we say do it. This place literally exudes energy and excitement around the 142nd Running of the Roses. It really is “the most exciting two minutes in sports” but I promise you’ll have way more than two minutes of things to do in Louisville. It’s a bucket list item after all, right? And we’re off….
- Transportation to Louisville
Flights into Louisville can be expensive this time of year, upwards of $700. Check Cincinnati or Indianapolis airports for cheaper flights and rent a car for the 1.5 – 2 hour drive to Louisville. You can also go in with friends and split the rental of a large SUV or a van and make the drive from your hometown to Louisville.
- Where to stay (couple of options here)
As you can imagine Louisville has all the major chain hotels like Marriott, Hilton, Hyatt, Starwood, and the list goes on, so checking hotel booking sites would be your best bet. Just need to book early so you can find one that’s in close proximity to the race track.
If you are looking for a local experience and have the coin try out 21C Museum Hotel. It’s a 91-room boutique hotel, contemporary art museum, award-winning restaurant and cultural civic center. What’s not to love?
Lastly, want to save some money? Go in with some friends and rent a house on Airbnb or VRBO. I’ve heard that many of the celebrities visiting the Kentucky Derby do this for the “privacy” as well as the close proximity to the track.
- Distillery Tours are a must-do (check website for hours of operation)
- Woodford Reserve – about an hour drive from Louisville. It’s absolutely gorgeous, and the tour is interesting and includes samples – duh – and a legit gift shop. Plus you drive through a Thoroughbred horse farm.
- Buffalo Trace – earned the title of “world’s most award-winning distillery”
- Four Roses – Built in 1910 and on the National Register of Historic Places
- OR Hop on a distillery bus tour http://kybourbontrail.com/map/
- Distillery “outposts” have opened in Louisville on Main St. You can visit Heaven Hill or go by Old Forester in West Louisville, but keep in mind these will most likely be packed on Thursday.
- Appropriate Attire for the races
The racetrack is decorated all in pink and the more than 100,000 guests are asked to THINK PINK and incorporate pink into their attire. This homage is paid not only to the Oaks official flower – the stargazer lily – but it’s in an effort to raise funds and drive national attention to the fight against breast and ovarian cancers. Churchill downs encourages you to wear any color as long as it goes with PINK — from hats to handkerchiefs, suits to sundresses and sunglasses to stilettos (or maybe your wedge)!
AND You can show off your pink duds on the pink carpet in the Longines Kentucky Oaks Fashion Contest, for an opportunity to win a Longines time piece.
Men and women attendees pull out all of the stops when selecting their attire. There are no hard and fast rules, partly because it depends on where you sit.
- In the reserved seating areas ladies typically wear spring dresses/pants outfits by designers like Vineyard Vines or Lily Pulitzer
- Derby hats that coordinate with your outfit are a must OR even a more recent trend, the fascinator, works just as well and won’t give you hat hair.
- And PLEASE make sure you wear a comfortable pair of shoes (cork wedges/sandals, etc) or have a back-up pair of flats since you will be doing a lot of walking.
- The modern Derby man usually wears lots of color.
- Pants are usually sun-drenched, tropical colors in bold stripes or busy plaid and bright pastels.
- If you want a polished look, try a classic navy or seersucker blazer
- Most men wear a necktie, but a bow tie is always a good option. Vineyard Vines offers an array of Derby-themed ties and bowties.
- Top it off with a fedora or bowler hat for a complete Kentucky Derby look and your all set.
- Kentucky Oaks is WAY less crowded and less expensive then the Derby
On Friday – The Oaks will give you an awesome experience at the Downs, the crowds aren’t nearly as bad and you can actually see the horses! There are several ways to buy tickets. We recommend buying a box – for six (6) people it’s about $120/each. On Derby day it’s more like $700/each for a box. If you are worried you might not see Danzing Candy cross the finish line, then make sure you get seats around TURN 2 – that’s THE best place to view the track. Oh and lots of local celebrities and horse enthusiasts will be in attendance so you can’t beat it.
- Take a trek to the Paddock to see the horses
If you are attending the Kentucky Oaks on Friday make sure to walk over to the Paddock BEFORE the race to see the horses. This is likely the only time you’ll be able to see them up close.
- Betting lines are long on Derby Day
If you have time, try to get a race program the day before Derby Day and look online so you can go ahead and plan your bets. Bet windows are awful on the day of the Derby. Seriously, you could stand in line for 30+ minutes to place one bet, so the SECOND you walk in the gates on Saturday for the Kentucky Derby, make ALL YOUR BETS for the day (lines get cray long after that).
- Traffic is crazy trying to get to Churchill Downs
Our recommendation is to get up on Saturday, have a nice breakfast, a few mint juleps and take a cab or Uber to the track around 11am. This is better than getting up super early and fighting all the traffic. Try finding a cab near Bardstown Rd. – there are “cab drivers” everywhere on Derby day that put signs in their windows for like “$20 to the track”. It’s the best.
- Best place to get pictures
Go in the front entrance so you can get some cool photos in front of the twin spires with the Man O’War statue, the Churchill Downs sign, etc. You won’t regret spending time enjoying this with your friends. Selfie anyone?
- You MUST experience the Infield at Churchill Downs
The infield is basically Louisville’s answer to Mardi Gras, complete with 80,000 of your closest friends partying with you. Tickets are available for $60 and you have to bring your own chair/picnic blanket to watch the races on the world’s largest 4K video board. If the weather is great you will have an awesome time. Keep in mind the likelihood of seeing a horse from the infield on Derby Day is .00001% – but like we said there are plenty of TVs, great food, drink stations, Vineyard Vines tent, and so much more. It’s crazy, but REALLY fun.