A Guide To The Kentucky Derby

Updated: Dec 16, 2020


For some people, Christmas means the gift of giving, maybe stuffing your face with every food in sight (me), maybe you just want Christmas to be over because you are dead inside. But for me, Christmas this year came with the gift of the Kentucky Derby, an event I have had on my bucket list since the age of 7 and started watching television other than Rocket Power.


One of the oldest sporting traditions in the United States, the Kentucky Derby is dubbed "the most exciting 2 minutes in sports" and for good reason. Horses galloping toward the finish line, turning corners on a mud soften track while tirelessly passing other jockies is truly something I will never forget. My dad decided to be clever (apple-tree) and wrapped up a case of mint julep syrup, a framed photo of the races last year, with cut outs of my mom, himself, and my faces in the crowd and on the horse, and lastly, our plane tickets to Louisville. After shattering everyone's ear drums from screaming, May truly couldn't come soon enough.

The greatest advice I can give to you in realm of planning a trip to the Kentucky Derby: PLAN EARLY.  As fun and spontaneous as it felt during the holidays, the same didn't apply as we scrambled to plan in the few months we had.

Where to Stay

Ah, Louisville. Spoiler alert: it's the Stockton of Kentucky. Be mindful of where you chose to stay, however, I recommend staying close as Kentucky's weather can be unpredictable and it is worth the money to save in realm of parking, taxis, & ultimately being stuck in traffic. We opted for the Four Points Sheraton, which is 1.1 miles from Churchill Downs. There is a bridge that separates you from the venue. However, note to the gals reading here: uber will come & get you, however, they can't simply drop you off right next to the venue. You will be doing some walking, which means wear some decent shoes! We'll talk more about dressing for the part in a later section, but you can always opt for some more luxurious options closer to downtown at the Hilton Garden Inn or the Residence in by Marriot

What to Wear

My favorite question! I arguably had more fun picking out my outfits than actually watching the horse races, fact. The Kentucky Derby is truly the time to go ALL OUT with your choice of dress, and hat. But tread lightly people: IT IS ALL ABOUT THE HAT. Pick your hat first before you buy your dress and work around the hat itself. I suggest buying something extravagant and buying a simple dress to make it really stand out.

For hats, you can't go wrong with something custom. I found the hat I wore with my white dress from etsy for around $70, which is definitely a little pricier for a hat you'll wear once but it truly was everything I wanted! Plus you'll now have a hat to wear if the occasion arises again (disclaimer: I wish there were more horse races in California). This etsy boutique truly does have an amazing selection of hats, I also loved this one. YA'LL. My hat I wore on the first day was $5. NO JOKE. For expensive items like these, you save save some major cash by visiting Poshmark for lightly used items such as these. 

As for dresses, there are so many affordable places online to get something trendy, easy, & can work around your big ass hat. Favorites of mine include Asos, Lulus, & Showpo. For more designer options, places like Nordstrom & Draper James have absolutely adorable dresses you'll wear time and time again. The Kentucky Oaks, hosted on Friday, is themed pink for breast cancer awareness and your dress (or hat!) should reflect! The day of the derby, Saturday, is a completely free day to dress as you like. 

SHOES. Okay ladies, wear comfy shoes because you will be in them all day long. I opted for something with a small, chunky heel so I still had height, but was still comfortable. These shoes are the ones I wore to the derby and would highly recommend in realm of style. You will be walking around all day and needing something cute, but functional. 

As for Jackets, the weather is incredibly unpredictable during the early May months and it would be wise to bring a light rain jacket just in case showers spring up. Bring something to cover your head, like this option as you will have to carry it around quite a bit!

Things to do in Louisville

Arrival in Kentucky is entirely dependent on where you are coming from, but for Californians I would recommend departing on a Wednesday as the flights can take quite some time to get to and from this part of the coast. Friday and Saturday are the main events, so you'll have a nice day and night to explore Louisville.

There are several ways to spend your time here, but eating should definitely be on your list. Butchertown Grocery had the unbelievable fried chicken and waffles featured above and honestly worth a stop. This restaurant is located incredibly close to Copper & Kings, an up & coming brandy and bourbon distillery. For other fun restaurants, The Eagle , Doc Crow's for BBQ, and The Silver Dollar are all amazing options. In the Silver Dollar Area, called Clifton, is a great place to go out as well. 

On that note, one thing I would absolutely book ahead of time is a trip to the bourbon trail. Places like Angel's Envy, Jim Beam, & Maker's Mark all have a home here. Now, I'm not the biggest fan of bourbon, but it's essentially your moral imperative to try it while you are there. Book your tours on the webpage ahead of time to ensure you have a spot the week of. They were full when we got there and didn't plan properly!

Where to Go Out

Little known fact (to us west coast kids): Kentucky likes to party. Truly felt right at home in their fun, unique bar scenes and amongst them a slew of bachelor parties & fun southern folks. The Red Herringhad some amazing craft cocktails and we became friends with quite a few characters. Tin Roof is another fun spot to get your shoes stuck to the floor like a college fraternity basement. They also have live music!

Speaking of alcohol, at the derby there are a couple signature staples you must try. The mint julep is an absolute must, as well as the pink lily, a vodka drink featured below. Betting on horse races is way more fun buzzed: fact. Although I did bet on Irish War Cry and he came in dead last so..

Consider Upgrading

Okay so this was mainly due to us booking WAY too close to the event, but consider purchasing an all inclusive package, like the Fillies & Lillies event is something worth looking into. This event gave us all access passes to a private, indoor area with insane amounts of food (the seafood bar was in my dreams), private betting areas, TV's to watch the races, games, drinks & I do need to mention this again: INDOOR area. The weather in Kentucky is incredibly unpredictable with rain storms and you will get cold. Having an area to visit when it's nice will ultimately benefit you as well as keep you dry. The event also hosts a private concert with dinner the night of the Kentucky Oaks with an open bar! An incredibly fun way to meet people and see some live music!

The Kentucky Derby is an event myself and my parents can say we will honestly never forget. Comment, like or subscribe for more bucket list events like these this spring. Mark your calendars for May 5th to watch!




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