I was the race director for my club for a couple of years. I'm assuming you are interested in doing an amateur race, at least for a start. Putting on the race isn't hard, but it's not easy either. There are a lot of administrative details to think about, and organization and preparation are key. For my club's races, the biggest challenge was dealing with government officials to get road permits, special event permits, and to line up police support. Each year I did the race, the process was different, and each year, the instructions they gave were conflicting, misleading, and wrong. I wanted to strangle the bureaucrats, but since it was their approval I needed, every time I got frustrated with them, I had to swallow my true feelings and say "oh, OK, sure, I'll be happy to do that." But I think this is probably a very local thing: hopefully your government agencies will be easier to work with. The other big challenge is finding a suitable race course. Doing a true road race is difficult because it ties up the road for long periods of time, and even coordinating a rolling blockade is not easy and requires even more police support (which you will be paying for). You should also come armed with a thick skin, because you will get complaints from all sides - whiney prissy racers, people who can't use their roads because of a bunch of *%#$ bike racers, and so one. In the few years I did the our race, I had some memorable moments, such as: 1) being threatened with a lawsuit from one of the largest property management companies in the country; 2) watching an ambulance drive onto the course in front of the pack on a downhill during a women's race; 3) having some choppers (motorcycles) ignore the road marshal and drive the wrong way down our course; 4) one year holding the race on the *hottest* day of the year (and I was out there for 12 or 14 hours); 5) having one guy sign up and show up for the cat 3 race without ever having done a bike race before (he chose the cat 3 race because the cat 5 and cat 4/5 races were already full). Compared to all this, the usual assortment of crashes, last-minute registrations, and racers whining about their 34th placing long after the protest period has ended, will seem trivial.