2011 Kentucky Derby: Millionaire's Row, the Oaks and More

Hundreds of thousands of fans descend upon Louisville, Kentucky for the Derby at Churchill Downs each May. A unique subset of the annual visitors are given the opportunity to mingle with the insiders—the fortunate few who watch the festivities from Millionaire’s Row.

Overlooking the grandstand, far removed from the hedonistic infield, Millionaire’s Row acts as a refuge to the craziness of Derby weekend. Thanks to the generous people at Ram Trucks, I was invited into the exclusive circle on the fourth floor to experience The Kentucky Oaks, the historic race day and festivities before the Derby.

Think Gone With the Wind meets The Real Housewives.

The dress code is immaculate. Magnificent sundresses have been sewn from every pattern and colored fabric imaginable. The outlandish Derby hats somehow work—they’re like nothing you’ve seen on television; they radiate. Four-inch heels are the norm and a large handbag is preferred (easy enough to sneak in a pair of flats for the painful strut back to the limo). 

The men are confident. Pink shirts, bright bow ties and seersucker suits are everywhere—it’s like going to a frat party only everyone is polite, the food is outstanding and frosty Mint Juleps have replaced the cheap beer. There’s an unspoken camaraderie on Millionaire’s Row, which often results in a casual head nod and nothing more.

Millionaire’s Row has a long-standing tradition of hosting "the rich and famous" come Derby time. Recent celebrity appearances have included The Queen of England and Prince Phillip, Michael Jordan, Kim Kardashian, Terrell Owens, supermodel Marisa Miller, Eli Manning and many more.

Some come to people-watch, but most come for the real action. To truly hang on Millionaire’s Row, you need to bet on the ponies. It can get confusing at times but the key is coolness. Always remember this simple horse-betting protocol and you’ll be in the clear:

1. Start by announcing the race you’ll be betting on.

2. Tell the cashier how much money you wish to wager, on which horse and what place they will finish.

3. Win is to win, to place is to finish first or second and to show is to finish in the top three.

When the races are a few minutes from start time, there’s a mad rush to place last-minute wagers. The bigwigs toss out trifectas, superfectas and exactas, but the simple way to curb inexperience is a Julep. If you lose, take it in stride and do like the millionaires… “It’s just another contribution to the Race Gods.”

My unforgettable experience was only possible thanks to the generous people at Ram Trucks and their ongoing involvement with the Kentucky Derby.