The 139th Kentucky Derby - And They're Off!

Starting bright and early on Saturday morning, thousands of lavish-hat clad women, and dapper gents teetered and shuffled excitedly through the infamous gates of Churchill Downs eager to begin socializing and wagering on their favorite horses, jockeys, and trainers. We excitedly made our way up to the clubhouse terrace level where everything I always expected the Kentucky Derby to embody was brought to life.

Everyone wore their favorite big Derby hats


After being wished "happy Derby" nearly a dozen times, we made our way to our reserved table that was daintily decorated with roses - the official flower of the Derby, and an official playbook with race stats and line ups. An extra bubbly waitress with a southern twang appeared instantly, graciously offering us the traditional Mint Julep, and an assorted cheese plate. I sipped it bravely, hoping the whiskey would warm up my wagering confidence, and after doing my best to learn the stat lingo, I weaved my way through the tables and guests to the betting counters. Of course being 2013 there were plenty of electronic options for placing wagers, including mobile apps and a touch screen machine right at our table, but we chose the more traditional, and scenic route.


The table in the clubhouse, decorated with roses

Mint Juleps and Lillies for the Fillies at the Kentucky Oak

The clubhouse was filled, literally to the brim, with fancy hats of all sizes and intensities, from elegant feather collections, to triple tiered furry layers that put the Mad Hatter to shame; they were all definitely a sight to see. But the ladies weren't the only ones in their Derby bests; the gentlemen showcased a fine collection of classy sportswear, typically consisting of slacks, button downs, and freshly polished shoes, but there was also the occasional fashion dare-devil like former N*SYNC member and Dancing With the Stars contestant Joey Fatone who tempted the clubhouse dress code with a matching baby blue blazer and shorts combination that gave a more new age appeal.

Polka dots were highly popular at this year's Kentucky Derby


Laughter and chatter filled the room in between races, but the buzz was instantly lowered at the sound of the trumpet before the start of each race, followed by the swift-speaking announcer commentating on the position of the stampeding horses. The thrill of winning picks getting close to the front never died with each race that went by, and if anything, increased eagerness for the next one. Race after race we witnessed the quick yet graceful speed of the horses, and even though we were at the top of the stands and in an enclosed area, we could still feel the vibration of the pounding hooves as the powerful animals and lightweight jockeys crossed the finish line.

And their off!


In between two of the races, we were able to steal a birds-eye view of the Paddock and a Polaroid moment in front of the famous Spires when a wrong turn led us out onto the roof of a lower level building. We had a prime view of the horses getting ready for the next race as they made their way around the Paddock, and then out to the starting post, lined by onlookers that looked like mere floating hats from our point of view.


Horses being walked around the Paddock before their big race

The famous Churchill Downs Spires


A bird's eye view of the Paddock and Spires

Back inside, we indulged in another round of Macallen whisky tastings, chatted with new and old friends, and exchanged ensemble compliments, then finally made our way back to our table to start prepping for the main event, "The Most Exciting Two Minutes in Sports". I had been proudly sporting a pin all day like a pageant winner that said "My Derby Horse is: Orb", which I chose mostly for it’s amusing name, but after practicing picking winners for the previous eleven races, gathering lucky numbers from friends and family via text, and some wine and whiskey induced confidence, I put my money on my lucky horse.

Horse racing statistics , odds, and the Derby line up


Maybe it was good karma for wearing the pin, or maybe I really became good at reading stats, but the $50 bet I put on Orb (and the only bet I made above $2 all day) burned hot in my hand as I watched the number 16 horse come up from the middle of the pack in the final stretch of the Kentucky Derby, and cross the finish line first into the Winner's Circle. The feeling of picking the winning horse of the Kentucky Derby was truly a remarkable and memorable moment, especially when there were only a few people making their way to the betting counter to cash in on their winnings.  

The winning bet for Orb to win the Kentucky Derby


Lucky winners who bet on Orb to win the Kentucky Derby with their winning tickets


As the room quickly emptied, the exuberant energy remained, even despite the wet and gloomy weather. I quickly learned that ponchos don't work well with giant hats and stiletto heels, but not a single person seemed to mind.


Although it was a long and exhausting day, the fun didn't stop at finish line of the last race. We were among many who attended a dinner and cocktail party at 21C Museum Hotel, still sporting our Derby ensembles, complete with hats and of course my lucky Orb pin.


We chatted and sipped cocktails until our legs started to give out, but even as we were leaving the party, more people were filing in. Sunday morning sadly came too soon, but opening my hotel room door to the front page of the newspaper with the headline "Orb Wins" helped revive my excitement. 

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