unfortunately hitch hiking is pretty much dead. Done in by freeway's and serial killers

I think to start a trip like this, you should make a list of the places you are dying to see. Put them on a map and see if any route jumps out at you. You'll have to find routes that stay off freeways which is becoming more and more difficult to do.

Comfortable low-top running/hiking would be best. Plan on buying new pairs in your budget. And like Gershon said, plan your budget and double it.

I disagree with Gershon about preparing and planning. You'll never get out the door if you over-think this. This is a young, stupid decision that should be made while you are young and stupid. Plan what you can and make sure you have an escape plan, then get out there and have an adventure. Best of luck!