I wouldn't call him a hobo in any way, but if you really like a calming way of wandering around North America, I recommend checking out: Foresty Forest YouTube channel.
He lives in a van with a dog. And he will summit random mountains across Canada, go on hikes, cook some food in his van. There is a weird comfort that I think might echo with people who have a fascination with nomadic lifestyle.
Here’s a video that happened to come up on my YouTube feed today. It’s by someone doing what I’ve always thought of as the quintessential hobo activity: hopping a freight train. Beautiful scenery.
I suggest to look up his trip up from Mexico, following the migrant route. For a different view of the same trip, his travelling companion (automous something) has his own channel.
RanOutOnARail isn't really a hobo though ... I think he's a software engineer in Texas somewhere.
Hobo Shoestring has an interesting channel also, albeit with a home base. You'll learn a lot about trains, and hobos' most hated adversaries, the 'homebums'. :D
And of course, there's a 10x hobo, in stobe-the-hobo (RIP), well worth watching all his videos.
Love Shiey and he also goes on quite a few trips with this guy (https://www.youtube.com/channel/UC8iPVSFr42KUFf8DKsmnvSw) who is very well educated and more philosophical and artistic than Shiey. Like them both a lot, but they're different flavors of the same genre.
Haven't watched him in a while but in the earlier days, his production values were quite charming. He's at a great intersection of vanlife+summiting+pressure-cooking. Not much pretence or glamour.
I took a very long break as well, but I started re-watching again. For some reason, I have become very fond of the idea of finding comfort in routine. He posts a video and the format is pretty much the same, so I just play his videos as I go to sleep.
https://www.youtube.com/@forestyforest
He lives in a van with a dog. And he will summit random mountains across Canada, go on hikes, cook some food in his van. There is a weird comfort that I think might echo with people who have a fascination with nomadic lifestyle.