Samual,

Check out this site: http://imjustwalkin.com/

It's about a guy who walked across the country. I like his idea of a converted baby jogger to carry his gear. If you carry a pack on it, you can mail the jogger ahead if you do a long stretch of trails.

"Young and stupid" is a compliment. Those of us who are now old and stupid miss those days. Might be a good trail name, too.

You can overplan the trip trying to see interesting things people know about. But then you will miss the things people don't know about.