There exists a National Hobo Convention that may interest you. Your search engine of choice will reveal more information and I'd rather not duplicate it here. I went one year, probably back around 2011. It's in Britt, Iowa and is always on the second weekend of August (as I recall). It is a pretty laid back event and sharing booze gets you unlimited stories. I forget exactly when it started (I want to say back around the turn of the 20th century) and it's traditional to hobo your way there - but I've never done that. It's a little cheesy, but it's still worth visiting. You'll also get the chance to learn about the lifestyle and talk to some of the remaining old folks who partook of the life. Many of them don't actually keep going once they get pretty old. There's even young folks who still enjoy the lifestyle today. They're a bit like migrant workers and there's a whole lot to their culture that I'm not even going to bother trying to write about - as it could easily fill a book. Had my life taken a different turn, I planned on retiring by getting my Class A CDL, leasing a truck, and doing long-haul deliveries, exclusively to drop-off stations (as I'd absolutely murder someone if I had to drive a rig in the city). Alas, my life turned out very different and I'm able to afford an RV. I'm fortunate in those regards, but I'm unfortunate in that it remains in storage most of the time. I bought it new in 2008, a nice customized RV actually, and it has something obscenely low - like 62,000 miles on it. That's a damned shame. I have, however, taken a bunch of time to engage in wanderlust. I've been known to just hop in a car and not return for 6 months. I don't need a destination. I don't need an itinerary. I don't even need the RV, as my last really long journey was done in a regular automobile. (It involved a purloined pumpkin, ex-girlfriend remorse, and a car purchased for just that trip - namely an old '88 Honda Accord. It's a great, but long, story.) Hopping trains is dangerous. There's stories of serious injury and death - and they're fairly frequent occurrences. It's also illegal as fuck and the trains are often patrolled by both official lawmen and a police force that's dedicated to the railroad. There's a ton of stories about hobos being abused, including sexual abuse. Let's just say that the lifestyle attracts not just the mentally healthy people. It attracts people with mental illness, addiction issues, storied pasts, and people prone to violence. Which is not to say that all hobos are like that, but that a subset of them are legitimately dangerous. So, really, I'm not sure it's an attractive life for retirement. Most hobos, from the limited subset that I've met, 'retire' from hoboing and settle down. Curiously, many of them miss it and will still engage in hoboing from time to time, but they're often also homebodies with a mostly-regular life. If you go to the National Hobo Convention, you can meet some of the older folks and they'll tell you a bunch of great stories. (Bring a few extra bottles of not-expensive booze, and the stories flow like water from a tap. It's awesome.) Damn, I'm wordy today. Ah well... I wasn't doing anything better with my time and maybe someone'll learn something from, or enjoy, the absurd amounts of gibberish that seem to leap forth from my fingers today. I strongly suspect it has something to do with my recent rekindling of writing interests, but I've been pretty wordy for the past few days. (More so than normal!)