48 Hours of Kentucky Derby

As a first-timer there is a little you can do to really prepare for the Kentucky Derby except show up. Sure, you can have the perfect dress and hat, tickets, and a great group of friends in tow, but once you’re in, nothing is quite what you’d expect. It’s tailgatin meets an elegant country brunch, with a touch of old-world nostalgia and a whole lot of rowdiness. Here is what a couple days of Derby looked like for two SL editors.

Friday, May 2: The Oaks 

8 to 11 a.m.: Suiting up. This isn’t the place to skimp on on style. We partnered up with Gus Mayer for our Derby looks. Thanks Gus! And yes, phones are also a main accessory at Derby.



3:45 p.m.: Scoping style. Out of 200 contestants, Carson Cressley, Simon Baker, and Stephanie awarded best in show to this lovely lady who stood out in her quirky get-up during the Longines Kentucky Oaks Fashion Show.

Photo courtesy @KentuckyDerby

From right: Longine CEOs, fashion show winner, Simon Baker, Carson Kressley, Stephanie Granada @KentuckyDerby

5:15 p.m.: Drinks, like a local. We found our favorite mint julep at Rye on Market Street—not too sweet with a bushy sprig of fresh mint.

Photo by Hannah Hayes (@hayeshannah)


11:18 p.m.: Galas and secret concerts. Dierks Bentley and Miranda Lambert duet at the Barnstable Gala. Run by Patricia Barnstable-Brown and Cyb Barnstable (former Doublemint Twins), this soiree runs into the wee hours of the morning at their sprawling estate.  Other close encounters of the celeb kind include: Boyz II Men, Richie Sambora, Pete Wentz, and Mary Wilson. The takeaway—musicians love Derby.

Saturday, May 3: Derby Day 

10:42 a.m.: Haggling for parking. Cash is essential. And we’re not talking the $10 or $20 we’re used to paying. If you’re going to be a high roller, you better bring some extra 20s.”

1:10 p.m.: Red carpet interviews. Laura Bell Bundy impresses us with her horse betting knowledge, and Johnny Weir tells us the inspiration behind his pegasus hat.

3:30 p.m.: Up-close with the horses. The saying “the fastest two minutes in sports” is no joke. We got the behind-the-scenes tour to see the horses go from paddock to finish line, and the whole thing flew by quicker than you can say “another mint julep, please.”



8:20 p.m.: Small plate-palooza at Ed Lee’s Milkwood. We can hardly resist ordering a second helping of his spicy chicken and waffles.



11: 14 p.m.: Party at Hotel 21C Museum Hotel. Morph-suited models, glitter-throwing performers, a chandelier hanging champagne server—this is how Louisville celebrates the end of Derby Day.

21c party


3:30 a.m.: Calling it quits. We make our rounds to some of the local bars where the festivities continue. It’s soon bedtime for these two editors, but Louisville was made for night owls. Bars stay open till 6 a.m. on race day.

So what did we learn?

It’s all about the hats.


Celebs have intel on the winning horse. Everyone told us they were betting on California Chrome, and sure enough that was the winner.

Restorative tea breaks are a must. We took ours at coffee shop-record store hybrid Please and Thank You with their iced green tea.

photo 1 48 Hours of Kentucky Derby

Prepare for lots of food. Especially the pizza at Garage Bar. It reinvigorates the soul for more Derby Day antics. Order the Ham Bar as a protein-power appetizer. You’ll thank us later.

garage pizza


Surprisingly, Pete Wentz had some of the best advice of the day: “When you think you need another mint julep, you don’t.” The sun and bourbon has a way of catching up with you quick. Take a cue from the horses and pace yourself.

And finally, visit Why Louisville for local goods and eerily truthful fortunes.

Screen Shot 2014-05-05 at 3.51.51 PM

Were you at Churchill Downs this weekend? Tell us about your Derby experience! 




  1. Stephanie Ray Brown

    I loved this as a born and still blessed to be in Kentucky girl! Most people think if you live in Kentucky you attend the Derby. But truth be told tickets are hard to find and can be quite pricey.So tickled we were blessed to have these terrific tickets handed over to us for free…even if it was two days before Derby Day! We had quite an adventure on a first and as of now our only trip to the Derby. If you want to read more please visit my blog link


    .Hope it makes you smile as much as I did when I remembered this great event!

    May 30, 2014 at 10:08 pm
  2. Daniel Chamberlain

    Hannah, very nice article. We are so glad you had a great time in Louisville. Your magazine has been kind to our city and we hope to see you again soon! BTW, The pink mixer IS fabulous!

    May 8, 2014 at 8:23 am
  3. Alisa Boone (@BhamAdGal)

    Great job girls! You represent Southern Living well!

    May 7, 2014 at 10:13 am
  4. Lauren

    I love this! You should cover more events on the blog.

    May 5, 2014 at 7:18 pm

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