Kentucky Derby & The Great Waffle House Quest


Oh you fancy, huh?

Class. Sophistication. Elegance. All words I would have used to describe my expectations for the Kentucky Derby as I purchased my ticket to the infield. In a somewhat sporadic decision, I signed up to join my party girl Mattie for a swanky weekend at Churchill Downs. [I should have known better… enter flashbacks of Mardi Gras in NOLA with Mattie; circa 2009.] It started real darn spiffy, I mean look at this good looking group:

All Class Acts | Kentucky Derby 2015

I learned in the days prior that the Kentucky Derby I envisioned wasn’t quite the Kentucky Derby I’d find in the infield. It started with tales of hundred dollar dresses being torn to shreds and went on to include this quality vid of the “Kentucky Derby Porta Potty Run:”

While I can be quite rowdy in the circles I travel, I get pretty shy around people I don’t know. Luckily, this was one of the kindest, laughter invoking and welcoming group of people I could have been thrown into. I rode down to Kentucky with the “RV Boys” and that was an adventure in itself (#TeamAri). We rented an RV to serve as our home base for the weekend, which turned out to be one of the greatest ideas, ever.

rv boys
The RV Boys | Kentucky Derby 2015

We started off the day with some casual early-morning boozing, dress up, and photo taking at Mattie’s mom’s house nearby. We were feeling pretty cute, which was quite the feat because we didn’t go easy the night before.

The Gals | Kentucky Derby 2015

When you have tickets to the infield, you enter Churchill Downs and are directed to a tunnel that leads you under the stands and into the center of the track. On the way down, you get a minor glimpse of the race track – likely the only glimpse you will get all day. The infield is packed with people, concessions, beer carts, betting stations, more people, and more beer carts. Once you’re in the infield, you can’t really tell which direction the track is in (and you kinda forget there is one). All of the race watching we did was on this screen:

The Infield | Kentucky Derby 2015

The rest of the day is a blur. Partially from drinking, partially because I was having such a good time I didn’t pause to take note [or pictures for that matter]. We bet, we danced, we boozed, we got lost and then found – we had an all around great day. And on top of all that fun, 2/3 of the horses I picked for a trifecta placed so I won $68!

If you make your way to the Derby next year [You should. And, I’ll see you there], then heed these few bits of advice.


  1. Make a bet! You’re at the freakin’ Kentucky Derby.
  2. Dress nicely, but not in your nicest. I am a somewhat responsible human and I woke up with two footprints on the stomach of my dress and a muddy left foot.
  3. Don’t wear heels – we were on our feet almost the whole day. Flats are essential.
  4. Snag your mint juleps early – if you pass a drink cart with mint juleps, don’t let it pass you by! If you put it off, you’ll be waiting in a LONG line later on to get one.

    Mint Julep Stand | Kentucky Derby 2015
  5. Chairs – you can bring chairs in to Gate 3. But bring one you don’t much care about, chances are it’s not coming home.
  6. Bring Sunscreen – we had beautiful weather, but there aren’t many shady areas. Make sure you lather up that SPF.
  7. Bathrooms – plenty to go around. We were super impressed at how short the bathroom lines remained. Nice work CD!
  8. Just dance – my favorite part of the day was the enormous dance party that busted out near one of the stages. The DJ played all the hits from Spring Break 2005. My dance moves were likely just as good at these guys.
  9. Select a meeting place – it’s a hard event to be at with a large group of people. Navigating the crowd isn’t easy and you’ll probably want to walk around. Pick somewhere and a time that you can meet back up, or just get lost and enjoy it.
  10. Rent an RV – ours operated as our sleeping place and the transportation to/from the Derby. It was an absolute blast and got us all back/forth together and safely.
  11. Drink Water/Eat Food – This should be obvious, but I was so carried away I forgot to eat. Trust me, eat.
  12. Cash in. During the last race we stood right by the windows to cash in. This probably saved us a lot of time waiting in line as in moments the line stretched a good 100 people deep behind us.

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Waking up the morning after the Derby was a…. challenge… blessing… curse? I immediately threw back a few Tylenol & Tums and a glass of water. We hit the road relatively early to head back to Chicago. The boys had big plans for a stop at Waffle House. I personally had sworn off Waffle House after a bad experience during the aforementioned Mardi Gras trip. They insisted I give it another try.

After some #hiddenagendas, trials & tribulations, and a side of copyright infringement – we finally made it to a Waffle House. After a short wait, we were ready to feast. While the food and overall experience was much better than my last, the most positive part of the experience was the sheer enthusiasm from all of the gents.

Finally Found a REAL Waffle House

Overall fantastic trip and great experience with an even greater group of guys and gals. Stoked for the next one!

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