I will add a couple of random thoughts:
  • A good part of the challenge of doing 500 miles over 5 days are the long rides on consecutive days. If you go for something like that, make sure to ramp up your training so that you have long efforts on consecutive days. One needs to learn how to withhold energy on the first day to have something left in subsequent days. Also, you may wake up on day 2 and feel it is impossible to walk, much less ride. However, after a few miles on the bike, you will get back into the rhythm.
  • In long trainer sessions you may consider changing shorts midway. There is a lot less air circulation, fans and all.
  • As ny_biker mentioned above, figuring out what to eat and drink is another art. Some people find drinking their calories is easier than eating them and they use some calorie-dense drinks, for some others, including myself, it does not work. So, you need to experiment. I know people who do IronMan tris work on getting used to consuming the things offered during those particular events.
  • You mentioned you would do the ride on your cross bike, so perhaps investing in the right type of tire is something to think about (assuming you have knobby tires, and the ride would be on paved roads, slicks or file threads would do better than a tire with more grip for mud)


And, if you and your sister or a friends can get away, try to do a cycling camp. In my life, I've attended only one, a very affordable one (google Alabama Cycling Camp; there are a couple of videos in youtube) and it was great. Rode every day for 7 days, it was a great base for me last year. And, in February, going from Chicago, it felt like a luxurious vacation. In my group, all drove there, one from as far as Toronto.