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!)
I’ve been enjoying your writings the past few days. I don’t know that I’d call it retirement more an escape from the rat race. I’d love to here the Storey with the 88 accord as late 80s Honda’s hold a special place in my heart.
The story of the Honda and the Purloined Pumpkin is way too long to tell at once. There's a dedicated following of what I call "Pumpkin Stories" over on Voat. They are long and colorful, as such was an interesting time in my life.
It starts like many good stories do, with a woman. I've never been big on long-term relationships, but I'd been with this one for a while. It turned out, she was insane. Granted, I usually admire that trait in the women I sleep with - but this was truly insane.
She was a kleptomaniac, among other things. What is baffling is that I actually have a few bucks and there was absolutely no reason for her to steal. But, steal she did... I'll save that for another time, but let's just assume she was insane.
After our breakup, I bought a used 1988 Honda Accord LX and went over it with a fine-tooth comb. It was my passion for a couple of weeks and I buried myself in an engine rebuild, replacing most of the running gear, and giving it near-full restoration. Then, I decided I'd take it for a drive.
It drove well and I was trying to get over my relationship. I was drinking and drugging quite heavily. Sad, but true. I'd always been fond of drink and drug, and had been pretty functional at both. After I retired, it's like my brain realized I no longer had to be functional - so it wasn't. I was no longer a functioning drinker and user. No, no I was not! But, in my defense, I had a really good time.
So, I went back to my house, packed a few things and threw a couple of guitars into the car. I figured I'd be gone for a few days and that I didn't need to tell anyone. So, I didn't.
As I was leaving the State of Maine, I turned that car right around and drove all the way back to an area outside of Farmington, Maine. Why?
Well, I have a buddy with a "brown thumb." It's the opposite of a green thumb. Basically, anything he tried to grow (and he tried to grow many things) came out stunted or died long before fruiting. His attempts at growing a garden and weed are comical to the point where one might assume my recounting the tales were me being dishonest. They are not works of fiction, he's just really that bad at growing stuff.
He had a pumpkin. It was maybe 6" across. He was very, very proud of his pumpkin. He extolled the virtues of the pumpkin. He told us of his growing techniques, his fertilizer use, and how he was going to decorate the pumpkin for Halloween and make a pie.
I wish I could say this a better way, but the reality is that I turned around and drove the two hours back to his house where I promptly stole his pumpkin. I prefer the term kidnapped, as you'll later understand, but the reality is that it was a purloined pumpkin and I'd stolen it.
He did not know this.
I then stopped at a store and bought a burner phone, a bunch of minutes, a black magic marker, and a bandanna. I used those to dress up the purloined pumpkin as a pirate. I'd stop, not long after, and outfit him with little plastic swords that I'd acquired from drinks at a Chinese restaurant.
For the next six months, I drove (more or less at random) around the continental United States. Pumpkin only survived for about four months, but he was a wonderful travel companion.
Along my way of rediscovering Americana, I took many pictures of my stolen pumpkin and sent them to the original owner of the pumpkin. I used the above mentioned burner phone for this and refused to tell him who I was - and he never guessed. Later, after returning, I'd tell him about my deeds and, though it took some time, he forgave me and was understanding of my plight.
I went to tourist attractions, cheesy roadside attractions, monuments, fine dining, among other things. I'd take pictures of pumpkin in those various settings and send them back to the original owner of the pumpkin. Sometimes, I'd demand ransom. Other times, I'd say I was a liberated pumpkin and had gone off to live a life of piracy.
I sent him pictures of the pumpkin in front of things like Niagara Falls, from the top of the Empire State Building, visiting alligators in the Florida swamps, sitting atop a mechanical bull in a Texas bar, posing with aliens in Roswell, hanging out with his new best friend "Corn" in Iowa, the top of the arch in St. Louis, etc...
Basically, everywhere I went - so too went Pumpkin. We had grand adventures. Pumpkin and I sang duets (he had a pretty sweet falsetto), told each other bawdy jokes, and laughed until our sides hurt. I'm pretty sure Pumpkin was actually a lush. I'd wake up and find my booze and stash missing or depleted. I don't recall drinking or using that much, so the only logical conclusion is that Pumpkin was sneaking booze and drugs while I was sleeping!
In six months, I'd put some 26,000 miles on the car and suffer no major mechanical malfunctions. We traveled the country from top to bottom and side to side - multiple times. Pumpkin and I had a great trip and there's many stories of our grand adventure.
What happened to Pumpkin? He died.
He drank too much and stayed in the car one night while I stopped in Oklahoma to get off the road because the idiot truckers were trying to kill everyone during an ice storm. I had no problems driving, but the idiots there can't drive in snow or ice. The truckers were even worse - and this was a big storm and lots of people were getting hurt or killed in accidents. We'd decided it'd be safer to just find a hotel and hole up there for a while.
Well, Pumpkin was exceedingly intoxicated and stayed in the car. He knew enough to get into my pocket - but chose not to. During the night, he froze. His head got soft. Yeah, he got soft in the head and it wasn't long before his brain was mostly full of mush and he started to smell funny. It's his fault for not getting into my pocket and spending the night in the car.
Anyhow, we toured a while longer but he got less and less intelligent and started to smell pretty bad. He'd really liked the Floridian alligators so I drove all the way back across the country to give him a proper burial. By that, I mean I fed him to the 'gators. They didn't actually eat him. One snapped at him, breaking him open, and then he spit him out. Another alligator tried a bite but was having none of it.
I drove down Alligator Highway, stopped, and threw him at the alligators. I did this while a bunch of Japanese tourists stared on in horror. They looked even more confused as I explained that doing so was a long-lived American custom and was how we buried our pumpkins. I don't think they quite respected our traditions, but they did take a few pictures and left. I just don't think they get American values? I tried telling them that it was the same way my father, and his father before that, had buried their pumpkins - but they wanted nothing to do with it.
And, between those two events are a number of stories that involve myself, an '88 Accord, a road less-traveled, and a purloined pumpkin.
Sounds like the greatest trip anyone could go on. I’ll probably never get the chance to do something like that. Wife and kids and all, but man how much fun it must have been.
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