Thanks again, Hunter!
Hunter's Top Five Derby Do's:
Do go with all your peeps. The Derby is not the place to go for a romantic date with your husband, or a quiet getaway with your best friend. It's a more-the-merrier type of event, the kind where you invite everyone you in your email contact list and hope they all say yes. The chances for fun and adventure increase exponentially with every person you bring along with you.
Do try the mint juleps. The ones at the track are not the artisanal variety you might find in someone's home. They are pre-mixed and brought to you by Early Times, which is ok to mix with Coke at a football game but not the variety of sipping bourbon most Kentuckians would favor. It doesn't matter--get one anyway. The first sip is always the worst, and once you've finished that first julep, the second, third, and fourth will taste unbelievably refreshing. By the fifth and sixth, you'll be in exactly in the right state of mind to sing My Old Kentucky Home with appropriate sentimentality, even if you're not from here. You won't care if your Derby horse comes in last, and take it from me--the inevitable post-Derby stop at the White Castle on Second and Market will never again be so enjoyable.
Do wear comfortable shoes--they are the key to Derby adventure. There should be so much going on at eye level with your hat that no one will be looking at your shoes, and there is a lot of walking around at Derby. You're not going to have a whirlwind Derby romance or spot anyone from the Real Housewives if you're parked in Section 220, Row E, Seat 6 the whole day. Exploration is the key, so go to the paddock to see who you run into; go get a mint julep every hour on the hour; take a spin through the infield to see if you can spot any full frontal nudity, and then go place your bets where all the cute boys are--even if they're nowhere near your seat. All this requires being able to walk comfortably in the first place.
Do bet pedigrees. Handicapping horses is complicated business, and there are all kinds of ways people make their Derby picks. Some people choose the jockey silks they like best, a name that seems lucky, a successful jockey, a good post position, a favorite trainer; more advanced racing enthusiasts use mathematical formulas. An easy way that I choose a good horse is to learn the names of a few famous sires, then check the program for pedigrees. Gulch, Pulpit, and Storm Cat are a good starting point to betting on sires.
Do roll with the Derby punches. Is it raining on your Derby parade? Throw your hat in a plastic garbage bag, put it back on your head, and go seek shelter with someone handsome who may or may not treat you and your friends to dinner at Morton's later. Get separated from your friends? Don't worry about it--see where Derby takes you, because you might all stumble your way into much better seats and randomly be reunited in the third floor clubhouse, watching the featured race in a box next to John Y. Brown. Can't find a cab on Derby Eve? Jump into the first random van that pulls up with a bunch of strangers in it--I'm sure it'll take you where you need to go. (Ok, just kidding about that last one, but it really did turn out fine for my friends and me, even if it wasn't the smartest move we've ever made).
My point is, be open, because Derby will take you on wonderful, unexpected adventures. They can't be planned, only soaked with bourbon and met with willingness and enthusiasm, and the right pair of shoes.