The hardest part about backpacking trips are pulling the trigger. I was at a diner in Manhattan with my friend Tyler once. We couldn’t afford anything on the menu. We were in the Turtle Bay section of the city. We ordered something menial to not look like bums. Together we chatted about leaving New York. I had put off many backpacking trips since breaking the world record for longest road trip, as if I had gotten it outa my system; I hadn’t. I had never been to South America or Europe. Maybe I should do that. There was nothing left for me in New York and I needed to break free. How do I get back to where I was when I was a teenager when I roamed without a worry in the wind? 

Stop thinkin, just act.

My hand picked up my phone. It was sitting on the diner table lookin at me. Unlock. Chrome. Google. Kayak. I navigated to the flights tab and typed in… Hmmm… Madrid? Yeah. Madrid. Spain sounds fun. The price was like under $600. No roundtrip, just a one-way I was lookin at. But whatta I do if the prices jump and buying a flight back is mad expensive? Maybe I should buy the roundtrip.


What do you always preach, Greg? Never buy the fuckin roundtrip. That’s what Vagabond Secrets is all about (though I hadn’t written that book yet). Round trips take all the fun outta travel and you know it. Just walk your jabber and buy the one way; the rest will find its way to sense. So I bought a one-way ticket to Madrid. 


Now it’s official. 

I had no idea how to afford any of this, but the ticket confirmation was in my inbox and I left in a few weeks. That’s how it’s done. You wanna know how to take beginner backpacking trips? You buy the ticket to wherever you have always wanted to go without thinking about anything and trust that the rest will work out. There’s no particular “beginner backpacking trips” that are easier. The difficulty lies in you brain and it never goes away. It’s there every time so every time I must overcome my fear. Whenever I doubt myself, I know I’m going in the right direction.

Backpacking trips that scare me are always the best ones

I thought about my history backpacking around the US to get amped up and remind myself that nothing else is required to “becoming a backpacker” other than taking that first step: buying the fucking ticket. 

The goddam ticket.

That’s the hard part and once you buy it, the hard part is done. It’s like making a downpayment on an adventure. It always starts in the mind. Like the time I took a 100-hour train ride around the United States…

So this hot lesbian chick I used to wanna fuck sent me this article on FB about the “longest train journey in the US” and the blog post the dude that took it wrote. I read it. No way can this guy have the longest trip; I want the longest trip. Another challenge, I thought. Only there’s nobody challenging me except for myself. This dude doesn’t care about me. But I care about making the most of my ideas. So I decided, since he traveled about fifty hours on a train, to travel over a hundred.

But backpacking trips need a more substantial goal

Doing it just to beat someone coulda been enough (maybe), but I wanted something a bit more… non-dipshitty. I read somewhere about an author who took the train a long distance to finish her novel, and it struck me as a novel idea. I also read that some author took a flight to China from the US, then flew back right away just to have some alone time. I dug that method and solidified my Amtrak idea in my head: 

Use all these hours on the train to get inspired by the geography passing me by the window and the people I meet, and finish my fucking book.

Backpacking trips aren’t about actually putting on a backpack and walking around; they’re metaphors. It’s a pilgrimage. I don’t need to wear a pack and be on a bus or hitchhiking, or flying coach on a plane. Anything works. A backpacking trip just means me and a backpack and a notebook.

The best Backpacking Trips in the US are the ones that show you the entire country

That’s why I was so excited when I got on the train. But the only thing was… it was packed. Backpacking is full of small obstacles you can absolutely not predict. So yeah, the whole way from LA to San Francisco I listened to the guy next to me tell another guy across the aisle (letting his words arch over my head like they were playing football and I wasn’t invited) about his time in prison.

“I killed a man holmes.”

Then I fell asleep next to the murderer. In San Fran the train dispersed a bit and I had a seat to myself finally. I took out my computer and started writing.

We arrived in Portland and I called my mom.

“What are ya doin?” My mom asked.

“Oh, I’m taking a train a hundred hours to finish my book.”

Without any surprise at all: “Are ya gonna write the next great American novel?”

Trying not to get pissed the fuck off at such a shitty question: “That’s right. That’s what I’m gonna do. Oh and I’ll be stopping in New York so I’ll come see you.”

That’s how normal check-ins with my parents went. No matter how important backpacking the world is, family is always more important.

Anyway, back in Portland (Oregon), I switched to another train. Outside the window were tents and homeless people. In the train station there was nothing to really eat and I was starving. I got on the next train, which I had known was gonna take me through Glacier National Park. At the time, I had never been there, so I was pumped about that. 

Taste a bit of a lot rather than munch on a little.

There was an “observation car” on the new train, which was basically a glass-windowed car in the middle of the train where you could stare out the floor-to-ceiling windows and observe the world passing by. There was also a dining car, just like the movies. I loved it. I woke up every morning at 5AM and got coffee in the dining car and watched the sunrise in the observation car.

Somewhere along the 10-day trip I met a chick who offered me mushshrooms. I said no. She said why. I said I’m sober. She got uncomfortable. 

The train was empty for a thousand miles and I roamed around talking to as many strangers as I could, stepping off the train every few hours when it stopped at random towns to smoke a cigarette with the other degenerates. 

Did I mention it was New Year’s Eve?

I hate New Year’s Eve parties so I thought to myself: I should be on a train when the ball drops so I am not around people partying. Now I have friends to hang out with that are also sober so I don’t needa barricade myself in some moving vehicle every December anymore. That’s good. Anyway…

When the ball dropped people started playing guitar in the observation car. The girl that offered me shrooms was there. I wondered if I could somehow fuck her. She carried a hula hoop everywhere she went even on the train. I love hula chicks, they’re so aimless.

When I got to Chicago, I got off the train and stayed at HI Hostels (Hosteling International). It’s some hostel chain but what a great hostel it was. I hit up my friend I was in juvie with (well, it was a therapeutic boarding school but there seemed to be little difference) and told her I was in her hometown. We hung out and I got back on the train three days later. Before that I went outside of the hostel in the cold weather to smoke a cigarette and a homeless man asked me if I wanted to get beers with him.

“I’m sober.”

“I thought about getting sober once,” he told me.

“You should, seems like you need to.”

“Can I give you my number?” He asked.

Unsure: “Sure.”

Then one day he called me plastered and asked for help. I told him to call me back when he was sober so I could comprehend his speech. He never called back.

Backpacking trips for beginners are better when your home-life is sturdy

That’s why when I got to New York, I spent some time with my parents and told them all about my trip. It really was a nice half-way point on that train journey.

Look, the point here is not this train ride, it’s that a backpacking trip can be anything you want it to be so long as you are traveling through unchartered territory and making friends with strangers and listening and looking and writing. That’s the essence of travel. Let the thoughts come and go and listen to others’ thoughts come and go. It might suck, it might be awesome, but you’ll definitely remember it forever.

The moral of the story is buy a one-way ticket somewhere you’ve always wanted to go and just make sure you have enough money to get home. Then let anything happen in between. If you ever get nervous, you can always fly home.

Oh yeah, and I finished my book. If you wanna read it, it’s all about how I was sent to the most notorious therapeutic boarding school in America. 

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