Stories From My Hitchhiking Diary in 2010

Where I first started hitchhiking from.

Where I first started hitchhiking from.

The story of Caroline and I dating and getting married is an odd romantic tale of me visiting her on my hitchhike-around-the-world-trip (for free hopefully). However, when we started dating, and because I immediately knew we’d get married, I knew my plans would have to change.

To have a real marriage I didn’t want to do the hobo thing much longer, although I was hithchiking across the country for our first two months of dating. During that time I heard of a guy buying one dollar coins for miles, and got into the miles and points thing. A few credit cards, a few months, and thousands of coins later we were a newly wed nomadic couple.

But that story isn’t the one I want to tell today. Instead, I want to share with you my diary from hitchiking. During my trip I decided I would write down something about every person I got a ride with.

Here are the little notes I took on people from one trip, and an unreal story from the last ride of that trip. These were for memories’ sake, and I’d never thought I’d post them for thousands of people to read. Yet, I want to be true to what I have written down.

Ladies and gentlemen, let’s call this: the long way to Nashville…

My notes of those who picked me up:

  • Dick Humble (I’m not making that up): Picks up every hitchhiker, but doesn’t tell his wife.
  • Kyle: Single dad, wants to move to LA.
  • Carson: Walgreen manager.
  • Terry: Truck driver, likes Florida.
  • David: [likes Virginia], wife left, has 17 year old son.
    (Editorial note: I remember this guy’s story a bit more than that. First he was a super nice guy living in Petersburg, VA. He told me his wife left him and he would see her in town and he’d get on his knees in the middle of the street and beg her to keep the family together. Besides it being hard on him, it was embarrassing and he didn’t get to see his son much. So he had to move to Kentucky just to get away.)
  • Bonnie + Rodney: He use to hitchhike to Florida [back] in the day. They lived in Louisville, but moved because they love the quiet.
  • Doug: Hid in wheel well of a plane. Nam vet, been married 45 years, kicked out at age 10. Kill[ed] a car jacker in self defense in CA. Government has GPS in phone batteries and car clock.
    (Editorial note: This was a kind of helpless handicapped man picking up a stranger to be nice. I’m 100% convinced he was a little nervous so he told a story of the guy trying to steal his car and then flipping the knife to kill him, as a way of saying, “don’t mess with me dude”. But really, he was nice and that had to be a made up story.
    Also, because the government had a GPS in the phone batteries and car clock, or anything with a battery, he would sometimes leave his phone, take his truck without the radio and ride…)

The Crazy Story of how I got to Nashville:

(The names here are changed, because the info is actually personal).

November 29 – Kentucky

My last ride was unique. Amy & Brad picked me up and Amy, excited about helping me out, offered to go the extra 2 hours. But we had to pick up her friend, Wendy, and drop off Brad at work.

She felt extra compassionate because of recent tough times. Her 24 year old husband was out of work, and in anger management recently.  She, 20 years old, got married 2 years ago, and [got] raped, and had a baby around the same time.

She recently rescued a dog who couldn’t stay at her house and the pound would put [it] down. Wendy suggested that we take it to her ex-girlfriend, Becca. Becca waited for her dad to get home, and the dog stayed and Becca came [along too].”

Editorial note: for whatever reason I didn’t write the rest of the story in my notes. So after going from one trailor park to the next to pick up friends, we took off for the 2 hour ride to Nashville. Another thing I failed to mention is that the entire thing was odd because I got stuck on this bad on-ramp with no traffic. Like none. So I decided to go the wrong way (north) when I got picked up by Brad and Amy. So we kept going north to their home, to pick up everyone, to take the dog to see if the ex-girlfriend’s dad wants the puppy… the entire thing took hours.

So now we’re driving and it’s clear Amy is a saint. She picks up hitchhikers and puppies, and also she is a rock in the midst of her dysfunctional friends’ lives (although, they are nice too). She’s very gentle in her advise to be less promiscuous. They’ve all been raped, they all have heavy stories, and they all seem pretty poor. Yet, she’s still helping me out.

Anyways, Amy turns and says that she realizes that she actually has never had a license and she shouldn’t be driving. So she asks the next girl, who admits to losing her license from drunk driving. They turn to the next girl, who reminds them that she too lost hers from racing. So they all turn to me.

Long story short, I… the hitchhiker, drove the car to Nashville. I gave them gas money, and I think they were going to go to the mall there… not sure.


1 more short story.

For whatever reason another story continues on the same page, but I think it’s from a week later, never the less, here it is:

“At 10:30 this guy dropped me off and I got out next to a beggar with a sign. ‘Wanna get food?’ I asked, [and] he accepted.

We hung out at waffle house, Ken and I. He told me of his 9 year old who died in the Bronx by a drunk driver. He can’t forgive. The driver got 9 months.”

If I recall, he spiraled into depression and he hoped moving out there would be a new start, but it’s more of the same.



I once read these stories to a friend of mine, Ben, and he loved them. He later had an idea for a blog with a similar theme. Anyways, for the last many months, Ben has been hitchhiking around the states collecting stories from people.

If you want to check out his experiences, read: The Hitchhike Interviews

Maybe he’ll talk more about it, but I find a lot of people are willing to pick up people not just because of compassion, but sometimes because of loneliness too. You hear a lot of stories. You also just meet a lot of kind people, and a lot of old timer hitchhikers paying it back.

Maybe when his book is finished I’ll have him write a guest post on how to hitchhike. It’s like a science to him now, lol. Believe it or not, he loves it, and is darn good at it. I haven’t asked him anything, nor did I tell him about the post, but if people are interested, I’m sure he would answer questions gladly. Or drop him a comment with any questions on his blog or social media.

Anyways, thanks for reading my stories of old!

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  1. love it as I hitched hiked around usa from 1969 to 1982 it was a fun time —sex-drugs and rock n roll — getting picked up by hippy buses traveling from concert to concert was a trip
    I so wish I had took notes of my travels
    it was a great freedom and love for traveling
    I guess that’s why I sold everything and have been back on the road traveling for last 16 years
    thanks for teaching a old dog – new tricks

    • I’m sure those journals would have some wild stories to tell today. That’s awesome. Great to hear of someone in the sell it all and travel camp. :-)
      Thanks for reading!

  2. Great stories. Keep em coming!!

    • Thanks

  3. Please don’t keep them coming. Seems like all your actions are geared to some future book deal, along with Ben’s, except you’re not interesting.

    • lol. but ben IS interesting?

    • Tom, not sure if you’re on drugs, but there’s no possible book deal and if there was, it’s a terrible plan for riches.

    • Ignore the haters man. Some folks are jealous they have lived as rich lives.

  4. I would love to go hitching sometime just to meet all the crazy people who pick up hitch hikers. I think I’d need a buddy to go with though. I’d be bored out of my mind trying to do that alone, I think. This reminds me of Thumbs Up. It’s pretty popular and you’ve probably seen it. But, if you haven’t, just YouTube it.

    • Yea, well I can’t say it’s dull. The boring part is if your on the side of the road for a while. But at that point, they are actually nice breaks. Ben does couchsurfing too, so he’s in the car with people or at someones house. Doesn’t seem too lonely. YMMV :-p

  5. I love these kinds of posts, too. I’m all for you keeping them coming. I’ve generally found that the more affordably you travel, the more kind-hearted and interesting people you’re going to meet.

    • Well, I can confirm that some of the biggest jerks I’ve seen have been throwing fits at the checkin counter of fancy hotels.

  6. More please.

    • Well, those are most of the stories from that journal. I NEVER was a good journal keeper. But we had a funny hitchhiking experience in the Alps last year. We hitched from the IC Berchtesgaden through Austria and Germany. The irony is amusing.

  7. Hitchhiking has always been something I have wanted to try as a means of travel, but I am always concerned about safety when I think about it for very long…how did you stay safe throughout your travels?


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We have spent the majority of our marriage traveling full time, living out of hotels.   All the while, we list our expenses publicly, budgeting $25,000 a year for our nomadic life while still staying in mostly 4 or 5 star hotels across ~20 countries a year.
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