Well, if were going to be there, and I may or may not (somehow I missed the call for participants, I think, and haven't heard from NOMAD if I'm too late -- probably -- or not), I'd probably do a Tom Paxton song that most folks don't know, and I'd also do a song by my uncle Buddy, who was the first person I ever heard write his own songs. I might also choose from one Dylan song or another, though to be accurate, I don't really do that many Dylan songs.
Then again, for really well-crafted songs, you can't go wrong with Lennon & McCartney, particularly the early stuff. Pure pop fluff but so well-written. I don't do so many of theirs, either, but I can't argue that they don't fit the topic.
Woody, Eric Bogle, Fats Waller, Duke Ellington, Joanie Mitchell, Alaska Mike, the list goes on. Lots to choose from.
Maybe your approach would be to sing songs from different sources, so that not everyone does Dylan or Woody or whomever.
Hope I actually find myself there, just to see this.