Hats On Hats: 5 Rules For Attending Your First Kentucky Derby

The most famous race in the history of sports, The Kentucky Derby, takes place in my college town. The University of Louisville literally mandates that professors end their spring semesters before Derby weekend – because that is how seriously we, as a community, take this day. Whether attending Derby is on your bucket list, or you happen to be fortunate enough to travel to our neck of the woods on the weekend of May 7th, it’s important to be prepared and know what to expect.

Rule 1: Have A Travel Plan

When all else fails – rent a school bus. This is a sure-fire way to get to Churchill Downs. It’s inexpensive, and you can fit all your friends, because driving yourself is out of the question. Parking spikes to over $20 in some areas, and everyone knows you don’t do Derby sober. You roll up in said bus feeling like an intoxicated 9th grader, but by the end of the day, you leave feeling like a drunken champion. There isn’t a sweeter sight than watching the unprepared stragglers, disappear behind you in your fumes.

Plus, if you’re lucky like I was  last year, your bus driver’s name will be something cool like Wanita, and she’ll let you wreak all sorts of havoc on the ride down. Every time you take off and the exhaust pops, you can yell “WANITA, MOVE. THAT. BUS!” Or something like that.

Rule 2: You Can Tailgate Everything

While experiencing Derby in a lavish box seat or suite would be the ideal situation, most of us opt for the more inexpensive, but riskier option: The Infield. The infield is a melee of people literally sardine-d together in the middle of the race track. Lines for water bottles are an hour-long, the air tastes like alcohol, and the Southern sun is merciless.

If you want your Derby experience to be an all day affair, it is unwise to stay in the infield the entire time. You will be a vague apparition of who you once were if you do. The parking lot in Papa John’s Cardinal Stadium is your best bet to tailgate before you brave the masses in the infield.

Rule 3: Bring The Essentials: Food, Chairs, Sunscreen, & Comfy Shoes

When I pulled out my soggy, unappetizing sandwich last year, I felt like Simba against the stampede. There was no escaping the horde of intoxicated, famished college students. I know for some, beer is a major food group, but at least give yourself a chance at survival and bring some form of sustenance.

In addition, be sure to bring a chair and sunscreen, and don’t be afraid to suck up your pride and plop down in the shade. White Ray-Ban splotches across a beet-red face post Derby ain’t cute, ya’ll.

And while your 5 inch wedges look perfect with your Derby dress, comfy shoes are a must to have at the ready,  as you will most likely be on your feet most of the day, especially if you forget your chair.

Rule 4: It Is NOT A Sprint

Everyone is dressed to the nine’s, the Derby hats are outrageous, and the Kentucky spirit and smell of bourbon is tangible in the air. Why wouldn’t you be excited to be in our great city? One thing you have to remember is, to pace yourself. While it is important for the horses to go fast, the humans must refrain. Pacing is essential. Don’t finish all your alcohol before noon. Find a good level and stay at it, or else you’ll end up browning out and accidentally dumping all your betting money in a porta-potty.

Remember, Derby is a test of stamina for the spectators, not the horses.

Rule 5: Just Let it Happen

While planning the perfect Derby experience beforehand is a no brainer, what happens when Derby actually takes place can’t be stopped. So, just come with a good attitude and quite literally, just let it happen. You’ll have a better time that way, and plus, probably have some priceless stories from it. My personal favorite? I ran into a nun smoking a stogie in the infield. The best part was the nun was a man. You’re welcome, America.


When all else fails, just sit back, hold on to your Derby hats, and don’t be ashamed to find a patch of grass and take a short mental sojourn with your Mint Julep. At the of the day, when you survive and advance from the infield, that’s an accomplishment and a life altering experience within itself.

Welcome to our Old Kentucky Home.

jimmy fallon late night with jimmy fallon hay oh hay hey boys

Featured image via squirrel83 from Astoria, NY, USA / CC BY


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