Def. go grab the Colorado Trail guide book, and/or the Colorado Trail data book from the Colorado Trail Foundation, that'll answer almost any question about water and resupply, as well as the important bike detours you'll hit along the way.
That and the GPX, and you're set for a really good time. A good number of people were on the trail touring it last year, they all had smiles on their faces.
http://www.shop.coloradotrail.org/Guides_c4.htmI believe the GPX for the for the CTR contains waypoints that correspond to data in the databook (water!),
http://www.climbingdreams.net/ctr/Which is mighty helpful. That GPX also has all the bike detours.
If you have a ton of time, there's a terrible amount of things to do in the towns just mentioned, if what you like to do is even more hiking and riding - an obvious side adventure would be to summit Mt. Elbert, while around Leadville! Don't forget to pack enough food between resupply points!