Haahaha! Thanks everyone! I thought some sort of "train" theme at first, but can't find anything in that category matching it. I guess trapper hat it is!
I just started venturing into the vintage hat category, and Lo And Behold on one of my first missions I found a 1950s Dobbs of NY fedora! Spent some time cleaning it up with vinegar this afternoon (read that Naphta can cause some people to break out). While it was damp I was able to re-shape it just a bit so that it looks close to original. The feathers were in bad shape so I went to a fly fishing shop and got some new feathers that matched the old ones (mostly guinea) and....man....it looks great! Totally transformed the hat in just a couple hours!