The route? A 250-mile course between Las Vegas and Los Angeles. The date? March 13th, 2004. The prize? A million dollars? Wired News article on the Defense Advanced Research Projects Agency's Grand Challenge, a road race in which all the contestants have to be “autonomous motor vehicles” that can drive and navigate entirely without any human control. The piece points out that DARPA's conditions for racing are so stringent that the race probably can't be won given the current state of technology, and will be held again every year for the next few years until someone finally does cross the finish line.
This sounds like it could be fun. I think you could do it with the current technology, but you would have to be more creative in its application than most people who approach technological design are.