This is exactly the sort of thing I've been planning. I was going to leave to travel the world in August of next year sometime, starting from my home in western Canada and heading eastward through to the Canadian Maritime, then down through the United States along the east coast, doing odd work, perhaps teaching (I'm going to get my TESOL cert.) and simply walking, taking cheap buses or even hitchhiking along the way. The rub is that I must be in South America by December of the same year, Chile to be precise, which is where my road would eventually take me via Mexico, Central America and the Andes region.
6 years ago