Unless the weather is absolutely abominable, I'm thinking that the Rundill Road loop of Iroquois Park would make an ideal setting. It's 3.29 miles, and a lot of it is in the shade. Moreover, it's in a park, so there are water fountains, restrooms, and even a splash pad to cool off on. In fact, you could probably even do a '100 Miles of Rundill Triathlon' -- ride the bike, run to the splash pad, 'swim' in the splash pad, walk back to the bike, ride the bike, run to the ... you see where I'm going with this. Myself, I plan to skip the running bit.
The idea is to ride the loop 33 times without going insane. I hope to badger DD into setting up one of those little shelter-tent thingies that one encounters at 'cross races and such things with snacks and drinks and tools (just in case). Oh, and a cheering section. As you may remember from last year's 'A Good First Century,' he is the world's best boyfriend/team car driver/physical therapist/soigneur ever, and I have a feeling he will be happy to
If I'm feeling both organized enough and financially together enough, I might even (GASP!) make some '100 MILES OF RUNDILL' t-shirts. (I will at least make a design for iron-on tranfers!) Admittedly, they won't be as awesome as the '100 Miles of Nowhere' t-shirt that you get anyway if you sign up, but I'm actually a halfway-decent graphic designer.
If riding around Rundill Road 33 times sounds like your cup of tea, let me know (and let Fatty know between the 11th and 19th of this month -- April). His entry fee this year is $85, which goes to support the fight against cancer, which is extremely relevant to the state of Kentucky, which has some of the highest cancer rates anywhere.
If you are also crazy and you think 33 laps in Iroquois Park sounds like a good time and you want to join me, just give me a shout-out at taylosab [at] umail [dot] iu [dot] edu.