The Essential Guide: The Kentucky Derby

The Essential Guide: The Kentucky Derby

It’s that time of year again here in the Bluegrass state. It’s time for “The Most Exciting Two Minutes in Sports!” The first Saturday in May is the biggest day specifically in Kentucky and even most of the US. If you don’t know what I’m talking about, then you’ve been hiding under a rock your whole life. Yes, I’m talking about the good ole Kentucky Derby!  Here are a few tips and tricks for those of you coming in from out of time, and for those of you who may live local, but have never experienced the thrill of the Kentucky Derby!

1. Dress Up. Bring a Hat. A real Derby hat! Make sure it fits, it’s comfortable and that it doesn’t obscure your vision, even though most will say the bigger the better! Dress up, but be comfortable. Men, set aside the baseball hat and wear a cool Fedora. Ladies, if you must wear heels to the heavens, there are usually men selling sandals outside the track as you hobble back to your car. If you look good, you are going to feel good! As Churchill Downs says, “It’s a dress to impress day”. But a trick I learned a long time ago is to always pack a matching pair of “fast flats” in your purse. They are cute ballerina type flats that fold up neatly and fit right in your purse! or pack a pair of sandals that will fit seamlessly in your purse.

2. Arrive a few days early. The heart of Churchill Downs is the Barbaro statue in flight with Edgar Prado up. Bring a rose or a carrot (everyone else does) and leave it there with good wishes for a fabulous Derby. Attend “Breakfast at the Downs.” This is your chance to visit Millionaires Row. Enjoy a fabulous spread, Derby horses working out, fashion and flair. Next, head to the Kentucky Derby Museum (it is closed on Derby and Oaks day). Watch their award-winning movie “The Greatest Race,” which is a 360 degree experience. Bring Kleenex (You’ve been warned!). Visit their Finish Line gift store (the merchandise is different from the Churchill Downs gift stores).

3. Explore. As you approach Churchill Downs, its sheer size can be overwhelming. But in the days before the Derby you can explore it with relative ease as opposed to Derby day.  Next stop is the souvenir stands and the Churchill Downs gift store. Buy, Buy, Buy! Don’t wait for Derby day. You will be disappointed if you wait to purchase mementos on your way home after the Derby and discover that many of the cool collectible items are sold out. Realistically, you really do not want to be weighed down with Derby glasses for your Aunt Madea during the Derby. Now is the perfect time to buy and drag your loot out to the car. Speaking of cars, take time to make sure you know where you are parking on Derby Day. Parking at the track is reserved in advance. Check out the neighborhood parking lots or look into a shuttle bus.

4. Paddock time. The real Derby action is in the Paddock on the days before the Derby. You will notice that there are extra horses schooling for each race. Watch the clutch of horse paparazzi in the saddling area. When a horse enters the paddock with a security guard and the photographers point their cameras with hunting dog fervor, chances are that there is a Derby or Oaks horse present. Now you too can get incredible close up shots of the Derby horses.

5. It’s Derby Day! Be organized. Take time to be organized. Lighten that purse to essentials such as Kleenex, hand sanitizer, an envelope of betting money, racing program, binoculars, camera with extra charged batteries or your phone works just fine, a small notebook and pens for tracking your bets and toss in some snacks. Ladies, bring a towel from the hotel to cover your seat. You have paid a fortune for that Derby outfit and you don’t want to snag it on an old metal chair. When you get there, buy a couple of bottles of water (What? Are you nuts? Do NOT be tempted by Mint Juleps in the morning!!!). Stash your water and snacks for later in the day when the food/drink lines are long. Ladies, make sure you have a purse that zips shut (don’t tempt the pick pockets) and bring a plastic bag from the hotel to put your purse in. Trust me, at first there are rivulets of Mint Juleps and other liquids cascading down the grandstands but by the afternoon, it could be a river. Your lovely leather handbag is stained with spilled mint juleps from two boxes above you. Bring a plastic bag!

6. Bet. Bet on the long shots! Bet on anything that Calvin Borel is riding! First off in the morning, place some bets on anything that is 25-1 or more. Look, the long shots may have never seen 150,000 people yelling and screaming before. Adrenaline is a tricky thing and on big race days, long shots come in. As for Calvin? He is a hometown legend who will win something on Derby day.

7. Get Ready. Make sure you are in your seat when the Derby horses leave the paddock and enter the track. It’s a once in a lifetime moment as the band strikes up My Old Kentucky Home and 150,000 people sing. There is nothing in the world compared with the roar of the crowd as 20 of the nation’s finest three-year-olds leave the starting gate. You do not hear the horses as they thunder by you but you feel it viscerally in your soul. For the next few minutes, you are a Kentuckian — grateful to be alive and part of history.

8. Celebrate. You have just experienced your first Derby! The fun continues as you join in an exuberant crowd walking out. The neighborhood is flooded with Derby parties and you may find your outfit rated by porch sitters. You will find that even some of the local parking lots around the track will bring in caterers who have a huge dinner spread of Southern catfish, ribs, chicken, beans and greens available for purchase which is perfect for bringing back to your hotel room (because you just don’t eat ribs in your Derby outfit! haha).

9. Celebrate the thoroughbred. Celebrate; you were at the Kentucky Derby! Many people will never make it to the Derby, including those that live right here in the city of Louisville. Its an amazing experience and if you can share in both The Oaks and The Derby, amazing memories are sure to be made.  Enjoy my friends!

 Make it a great one my friends! Happy Derby Week!


Still looking for the perfect dress + hat for Oaks and/or Derby? Check out these amazing finds that all are $100 or less!




  1. May 2, 2017 / 2:26 pm

    I have always wanted to go to the Kentucky Derby! I don’t care anything about the race, just the people watching! Plus I really want a good reason to wear a giant hat.


    • May 2, 2017 / 2:27 pm

      It is definitely a “bucket list” item! It’s truly amazing seeing at the great fashion during Derby week! 🙂

  2. May 6, 2017 / 4:05 am

    Thanks, great article.