My First Hitchhiking Experience: The Shit Bag Man






“I’ve got this shit bag, mmaaan.”

He says it casually, like we’ve been friends for years. Southern drawl. Old smell.

Then he lifts up a small plastic bag (empty… thank god) from under his shirt to prove it. I ask him what happened.

“Drinkin’,” he says without shame. To emphasize his point or maybe just because he was thirsty, he took a big slug from his Busch Light can. With his other hand, he was navigating us down a windy country road towards Damascus, Virginia.

I was about 4 minutes into my second hitchhiking ride ever.



Today’s story is about a man who taught me there are many different ways to live.

We will call him Shit Bag Man (with the utmost respect of course), BUT if Jay (name changed) hadn’t hurt his knee, I may have never met him.

My first hitchhiking trip wasn’t my idea. I was just doing what I was told. Sort of.

Here’s the story…



There was no way we were going to make it.

Jay’s knee had gotten worse.


Our pace had slowed to a crawl and the kids were getting cranky. We were over halfway through our 14-day, 112-mile Appalachian Trail (AT) hike, but there was still 50 miles of Smokey Mountain wilderness in between us and our van. There was no way we would be able to hike that distance and be back to our school on time.

I was one of three leaders of our group, but I was the least experienced. Which means that when we had to decide who was going to hitchhike the 60 miles or so to our van… I was the obvious choice.

I didn’t complain either. Since I’d read Jack Kerouac’s, On The Road, I’d wanted to hitchhike. This was a good place to start too. It is common for hikers to catch rides to town for supplies.

Of course on that muggy Tennessee summer day, after I’d packed a small bag with only the bare necessities and set off on a nearby country highway… ALONE… I was shitting little kittens. Would this work? Is this really happening? I was trying not to visualize the most grotesque sexual acts imaginable being performed on me by some of the ugliest creatures alive.

It was gut-churningly horrible and deliciously exciting.

Anything could happen.


My first ride was from 3 Good Ole’ Boys in a pick up.

It was thrilling, chilling, hot, windy, and comforting to be zooming through Tennessee in the hands of 3 strangers I’d only talked to for 7 seconds. I’d thought they were going to kill me, when they turned around, but they were just checking on an antique car they wanted to inspect.

And when they dropped me off in Mountain City, Tennessee, I was adventure drunk.

The feeling you have when you think you might die (or get raped) and then you don’t… is about 100 times better than the feeling you have leaving work on Fridays.

I was ready for more, I only had 15 miles to make Damascus and I was fairly certain I would be sleeping in a bed tonight (maybe I could even get some pizza or a beer). I walked a mile or so out of town and stuck my thumb up. My good luck continued and in a short time I was running to catch up with a rickety van that had pulled over.

He said he was heading to Damascus and I eagerly hopped in.

We were off.


Meet the Shit Bag Man.

“I’m having a rough day, man.” He is skinny, dingy with working class dirt, and unshaven. In the next 20 minutes, he told me his life story as he swigs Busch Light (without offering me any) from a half empty case sitting on the floor between us.

We talk about traveling and he has done his share. He worked on a US Naval Submarine, so would go underwater for 4 weeks at a time. But he would also have 4 weeks of freedom after that. This schedule played havoc on his relationship with his now ex-wife. He calls her a “crazy bitch” and blames his drinking on her. Of course, he is still in love with her, which is why he mentions her so much in our conversation.

I’m really curious about his travels and I steer the conversation in that direction. “To party” was his reason for hiking the whole Appalachian Trail (2,179 miles long) three times. He was a wild one and I liked his stories.

They were different than almost anything I’d heard. And even though I didn’t want my life to be like Mr. Shit Bag here…

There was something about him that I admired.




I remember wanting to go “Ahhhhhhhhhhhhh (in a relaxed “I’ve made it” sort of way)” as I sat in his van.

Shit was clattering back and forth in his van. He was sorta drunk, but his driving was pretty good. And he was blabbering on and on about the sorted details of his life.

I think a lot of people would never want to be in a situation like this (maybe I’m wrong? Would you?). But I felt like this is what I’d been waiting for my whole life.

There was danger, stories, connection, windy country roads, beer, and as a kid fresh out of college who’d always tried to do the right and good thing, I was fascinated by this guy.

Drinking as he drives… throwing empty cans out the window and cracking another… This Shit Bag Man was as interesting as any character I’d read about in a Kerouac and he was sitting right in front of me.

Sure… I don’t want to be like the Shit Bag Man.

But who do I want to be?

Who am I?

And although I’d been asking myself and working through these questions more than most 23-year olds… this Shit Bag Man showed me there were a whole lot more options available than I had realized.

How did I want to live?


How about you? Does a stranger stand out in your life as someone who had an impact on how you wanted to live?

Even if it is in some weird way? Please share your thoughts in the comments below.

Your friend,



Ps. Stay tuned for more stories by joining our Posse (and get 5 free travel lessons to get started)!

13 Responses to My First Hitchhiking Experience: The Shit Bag Man
  1. Alex Lewandowski
    February 28, 2013 |

    Wow, what a beautiful story! “Shit Bag Man” sounds like an incredible human being- just like you said, like someone you’d read about in a book. I also met a random stranger once who probably changed the course of my life. It was on a camping trip with my family on the Chesapeake Bay the summer before my senior year of high school. His name was Art and he was a forester. At that point in time, I was “deciding what I wanted to do with my life” (when am I not?), and our conversations that week, ranging from geology and soil types to different kinds of trees and landscapes, led me to change my intended college major from English Literature to Environmental Science. He was just so passionate- I wanted to be just like him!

    Fast forward six and a half years later, and I’m about to set off on my first big adventure! Starting on Monday, I’ll be exploring the wilderness of Pennsylvania out of my car and writing about it. It’s funny how, even with all the twists and turns of life, the natural world and writing are still my primary passions. I guess it’s all meant to be. Today, I remember Art and his joyous enthusiasm by the campfire as the sun set over the Chesapeake. Thank you, Benjamin, for helping me remember! I am so glad that I found your blog and your site :) And I certainly enjoyed reading your memories of your first hitchhiking experience. Keep being awesome- keep being you!


  2. Maz
    March 1, 2013 |

    Once on a sunny day in Exeter I met a man with silver pen all over his face, a viking hat on, a wand, and baggy jeans, no shirt on. With him he carried a huge rucksack and a Macbook Pro. He had no shoes and one of his toes was falling apart. Around him were a group of people. You could see he was a socialite, he pulled out a clear acrylic ball and started contact juggling with it, and eating leftover takeaway food left by a wall. Everyone wanted to be around him and talk to him, young teenagers.
    He was so eccentric, talking about random gibberish. Everything about him was completely random. He introduced himself as Captain Jack Neo, and he didn’t ask me for my name – instead, he named me Crystal Funk. I ended up spending the evening with him, we went to the pub and played some music, talked a bit, and then I went home. When I woke up in the morning, I found one of his contact juggling balls in my pocket, and decided to learn the circus skill.
    I assumed he was homeless, and was completely enchanted by him. I wrote a song about him, tried to find him on Facebook, but no trace of him could be found. He’s infamous around Exeter though. I thought about him for months – he inspired me to be spontaneous, talk to new people with ease, and it just gave me some faith in humanity, that there were beautiful funky eccentric amazing people out there.
    Then one day at a free party, last Boxing Day actually, I saw him again. We instantly became friends, I got his number and Facebook name, and now he’s one of my best friends. Turns out he’s got a house, and lots of money – he had a car accident which left his brain slightly damaged, so the government pay for everything he does, which means he has no need to work. I was completely wrong about him. And to this day he still utterly fascinates me.
    Out of everyone I’ve met he’s definitely had one of the biggest influences on my life ever. Thank you Captain Jack Neo :)

  3. Jefferson
    March 1, 2013 |

    Hahaha, great post, man. I love the intro – it grabbed me right away.

  4. Thomas
    March 1, 2013 |

    I’ve had quite a few rides that have made a impact on me. But one that definitely still stands out today, despite the years that have gone, is this one: I was hitchhiking to another town where I went to school. It was only a 40-50 minutes ride, but damn – I was no where near prepared for what life story I was about to hear.
    So I was out there, hitchhiking on a beautiful summer day. I only get to stand for about fifteen minutes before a car pulls over. I jump in and present myself. And we start chatting away. Suddenly we hit a subject, or something, that just makes him spill out his life story. Deployed 18 times, through 20 years of military service. Kosovo, Afghanistan – name it, he’s been there. He told me of the terrifying things you see in a war. He told me about the friends he had lost under his commando. And even though this guy had went through all of this sh*t, and had been diagnosed with PTSD, he could still look at me with a straight face and say “I don’t regret any of it. Not a single thing or deployment: All those things made who I am today”.
    - At the time I spoke with him, he had left the military and was pursuing an acting career.

  5. Matt Clausen
    March 1, 2013 |

    Dood. Ben. This is excellent. All your posts relate to me in a way. You’re just real about it all and share your emotions. I’ve always had this idea to hitchhike, but have been held back my many different reasons. All I need is is that little bit of motivation and determination and this is it.
    You my boy, blue.

  6. Indiana Jonas
    March 3, 2013 |

    This reminds me so much of one of Jack’s quotes.

    “-The only people for me are the mad ones, the ones who are mad to live, mad to talk, mad to be saved, desirous of everything at the same time, the ones who never yawn or say a commonplace thing, but burn, burn, burn, like fabulous yellow Roman candles exploding like spiders across the stars, and in the middle, you see the blue center-light pop, and everybody goes ahh…”

    Really great story Ben!

  7. Ruthie
    March 3, 2013 |

    I think I have a lot of these situations, but strangely sometimes my experiences and travel life have become very surreal….at 19 I had run far away from my home, far away from my state, and even farther away from my country. I didnt tell anyone where I was going. I filled a backpack, bought a plane ticket from Mexico to Peru—-thinking what? I still couldnt tell you…..
    9 months later,and 6 countries later, I found myself in Ecuador. Tiny surf town, that smelled of salt water and community.
    The last night I spent there was filled with drinking, dancing,connecting, and an all night reggae show that seemed to involve connecting people in a very passionate way. The community aspects of SOuth America always amazed me, something that I indulged in, as I came from a sheltered life in Salt lake City, Utah;)
    Traveling alone as a female, left me to being very independent and having to be aggressive with how I presented myself.
    Of course the culture is very connected and sensual, especially when it comes to dancing…Everyone danced all night….talking over loud music, languages from all over, we created a contact language where everybody understood each other, through body language, gestures, and broken pidgins. I ended up dancing with a guy that was a musician—talked through the night constantly….—the conversations led me to thinking that what am I doing?
    Who am I?
    He kept telling me to accept and create. We have no control, but control of ourselves.
    We create our emotions and feed them out…..
    The night became a blur, I remember waking up on a cot in a wooden hut, smelling dirt that was in the air, looking around not really knowing where I was, but also feeling very comfortable.
    I saw the man that I had danced with all night and held passionate conversations with sleeping across the room.
    His happiness and energy still made presence even while he slept.
    I put on my sandals knowing I had to catch a bus out of town….I didnt want to wake him, but as I opened the the wooden door and sunlight peered in and shone in his face he awoke and looked at me while I was leaving,
    he smiled and looked at me like he knew I had to leave, but regardless he remarked,
    ” no te vayas!” I looked at him sincerely, smiled and thanked him,
    as I closed the door I heard him say “Recuerda lo que te dije”
    I spent the next five hours crammed in a bus remembering what he told me, and finding a little part of me of realizing who I was and what I wanted to do……

  8. Jamie
    March 13, 2013 |

    I met this girl in Latvia last summer while I was hitchhiking. We’d been dumped on a quiet road leading into nowhere and this girl, tiny, 30 years old stopped to pick me up. Me and another guy! No shit, she had a 6 month old kid in the back, was wearing braces that she just got fitted, and passed her driving test only 2 weeks earlier. “I used to hitchhike around Mexico and once hitched a ride from Greece to Italy,” she explained. She was heading South to do a bus tour in Spanish for tourists while her friend took care of her baby. She was a little bit of a hero for me. I never asked her name because it’s unimportant but I will never forget her story.

  9. Boris T
    March 13, 2013 |

    What I like about this story is how it was an unforeseen and unplanned event – the need to get that van, a few days early – that thrust you into this whole world of hitchhiking.

    However, I’m curious – did you find yourself in the end? What most influenced who you are and who you want to be?

    Being a 23-y-old, fresh out of college, and about to embark on a trip from LA->Boston in a couple weeks (and also someone who thinks a great deal about how people get to where they are and how they find ‘themselves’) I’m always curious to hear how people go from “shoot, I can do anything – what do I do” to actually finding a groove in life that fits them. Particularly, in this day and age where we have the problem of too much choice (yes I would argue this is a problem) and too much opportunity, and not enough hardship – our lives are more or less too easy (and probably a dozen of other factors) for us to discover what and who we really are.

    In my life, I have spent years developing a fundamental curiosity for every person and every hobby and every anything imaginable – and though I’ve found I can now relate to many people and fit in to many different social circles, am still at a loss for how to find the right ‘groove’ or path for me, when I feel like a traditional “engineer” or “social worker” or something doesn’t quite fit.

    Loved the article. Would love to hear your thoughts.

    • Benjamin Oliver Jenks
      March 13, 2013 |

      You sound like a Renaissance man, Boris.

      I don’t think I could ever go by one label. In fact, thinking about it how can we really use one word to describe ourselves. Are the people that do just different? Or have they forced themselves so they can be marketable?

      Probably both.

      But to answer your questions…

      Did you find yourself in the end?

      Yes. I can sense my true essence… relatively often.

      No. And I’m pretty sure I never will. There’s always more to learn.

      My self is like a huge puzzle. Some pieces are big (for me it’d be traveling, video, people) and some are small (I like wearing boots, drinking IPAs, having a beard). Some I’m testing out for awhile (never been into cats, but trying with some at my house) and then discarding what doesn’t work. Keeping what does.

      What most influenced who you are and who you want to be?

      Probably my family. There are some travelers. Others I saw and realized that is NOT what I wanted. Jack Kerouac’s book was big.

      But it’s been more of a series of puzzle pieces (to use the above analogy) putting them together, taking them apart, meeting someone new, leaving someone old…

  10. Izzy
    March 28, 2013 |

    What’s up man!

    This line brought a massive smile to my face “And when they dropped me off in Mountain City, Tennessee, I was adventure drunk.”

    It rung deep in my soul man.

    I think this post deals with what you and I have been discussing about being present (and authentic). You were fully in this moment – which allowed you to take it all in.

    The really awesome thing is that by being in the moment, you were able to step away from the moment and learn so much more from it.

    Funny how by being present we can make decisions that are great at the time, even better when we look back on them…. But also really stupid when we look at it from a “rational standpoint”. But life aint always rational, and sometimes we just got to embrace that.

  11. Mae Facheaux
    October 8, 2013 |

    I love this story. Seems 23 happens to be a more monumental age than I thought when I celebrated my birthday this year…. Like it’s a time for some to be like, “Okay, what now?”

    There are some strangers who really changed my life and how I saw the world.
    I have always lived in Louisiana… traveled some as a kid, but purely on a tourist level… and never felt like I really belonged anywhere.
    In summer of 2004, just before I entered high school, my mom & I went up Maryland for a few weeks for her job looking after her friend’s son. We stayed in their rent house in this little neighborhood in a suburb of Ocean City.

    Not long into our stay, I noticed that the house across the street had two boys about my age & friends in & out all the time. I was shy & cautious, so it took me a long time, and a goddess empowerment spell to build up the courage and speak. (I don’t know why I still struggle with shyness when putting myself out there almost always serves me well.) I can’t remember the details, but I ended up getting invited to the younger son’s birthday party & meeting all their friends.

    This group was like none I’d ever met. More cultured, intelligent, & badass than pretty much everyone my age back home. The two sons almost looked like members of Led Zeppelin, played guitar, and smoked reefer in a little bean bag chair & blacklight-filled closet.

    I had a little early teen fling with the older son & thought I fell in love (silly girl!) just before the boys had to leave for their father’s for the summer. Those nights, with them & their friends… discussing music, wandering the suburban streets past curfew, and walking/skateboarding/biking/rollerblading to the shop on the edge of town completely changed how I saw the world.

    Even after they left, I still had a bond I’d made with their mother & I would spend time with her… I went with her on errands and she took me antiquing in a neighboring town. I only knew them for a few weeks then, and have seen them once since, but they will always be close to my heart.

    Let your freak flag fliegen!
    <3 Mae Facheaux

Leave a Reply

Wanting to leave an <em>phasis on your comment?

Trackback URL
Subscribe for Sauce
Get Daily Travel Tips
Powered by Aweber Wordpress Plugin and Passive Income.