The infield is basically the same crowd as a NASCAR infield, so you'll see all types. The chicks in the sundresses and big hats are NOT the ones that will flash for beads. Some of the boobs I saw, I wish could be un-seen. I also saw a drunk, distracted guy get picpocketed (it's a huge crowd, use some situational awareness), and some guys get into a fight that involved a julep glass getting smashed into a face. I doubt that will happen where you are, but if you're curious, there is a tunnel from the "real seats" into the infield. If you want to get a julep, they're either 7 or 9 bucks, and it's basically a few shots out of an Early Times mint julep bottle and a ton of ice poured into a glass that's available at any liquor store in Kentucky for $2. There will be insanely long lines for the bus, so getting out takes forever (assuming you're parking at the fairgrounds and taking the bus instead of paying to park in someone's yard). As for partying the night before/after, I'm more of a fan of Bardstown Rd. (i.e. The Highlands). It's more of a college, artsy, local scene. But if you're downtown, you'll probably go to 4th Street Live. It's kind of like Beale Street meets the mall. Either way, the bars will be open until 4.