Our speaker sounds like a tramp. And we mean that in the good way. The way that he would use the word. The way we see him, he spends a lot of his time outdoors, in the wilderness, or on the border between civilization and the wilds. He's a man who can build himself a cabin with his own two hands, who can fell the trees and plane the wood.
And, most importantly, he's still got a lot of leavin' left to do. This is not one of those settler folks who builds a home and then sits pretty for the rest of his life. He'll keep heading west no matter what.
Even though he dislikes many of the comforts of the civilized world, he feels buddy-buddy with his fellow pioneers, who come from all walks of life. He spends time with both "the righteous and the wicked," embracing people of all kinds and occupations (line 66). As long as they're willing to be on the move, he'll be happy to give them a friendly pat on the back.
But he also has this odd relation to these pioneers. Their friendship is not without its hiccups. On the one hand our speaker considers himself one of them—one of the pioneers. But on the other hand he stands a little apart, describing as from the outside, and calling them his "children" (1). His work, as he sees it, is to praise them, to do his own pioneering as a bard, a poet of this new world and this new group of people who call themselves Americans.