I remember long ago there was a scarecrow boss that could be accessed from somewhere close to Homestead to gain a cool hat, but there was a specific way to do it. The boss looked like a scarecrow .
Don’t think there is one. I assume you ran into a random hero with a random drop
There is a secret quest. I have not solved it yet and not read the thread, but maybe this is what you are looking for.
Cannot recall what you are referring to OP, but while we’re on the topic I must say it’d be pretty wicked if Harvestmen did have their own MI hat, maybe boosting Blade Arc like the Harvester Stone or boosting the Occultist’s Raven summon (ravens, crows, same shit amirite?).
It’s a rather large unkindness to say that, although telling the two apart at a glance is just murder.
Good one! 
I probably know what kronuscde is speaking about. I also managed to get right to this boss some time ago. But it’s still unclear how…