Cumberland Blues- Grateful Dead
Easy Wind- Grateful Dead
Pastures of Plenty- Solas (The Woody Guthrie song)
Gum Tree Canoe- John Hartford
Boll Weevil- Old Crow Medicine Show
Mississippi Boll Weevil Blues- Charley Patton
Navigator- The Pogues

Good luck with this project, seems worthwhile and I'm digging the playlist.