The $285 Freight Train Hopping Experience

I ducked down and walked slowly toward the freight train as it rolled to a stop. Concentrate, I thought, trying to mute the sound of the gravel under my feet. I stopped three feet in front of the railway car, and saw it was the one I wanted. It was basically half of a box platform for a bigger transport container (the same as transport trucks haul) and there was a five by six foot empty space behind the giant box. Perfect.

I took a quick look around and threw my guitar bag over the rim. I pushed myself up by my arms and toppled in head first, my shoe catching on a metal hinge that jutted out.

I loved the adrenaline rush that I always got when I climbed onto a train, and today was no different.

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Hitchhiking Canada, Age 20. Part 3: Friday The 13th In Manitoba

I was staying at a youth hostel in Regina, Saskatchewan when I met her for the first time. It was October and apparently the off-season for tourists in Saskatchewan as she and I were the only guests that day. She said her name was “Hanna” but it was spelled Chana.

She arrived late evening, as I was making my dinner in the basement kitchen. She was was dressed kind of ‘hippie’ and was pretty, which was accentuated by a positive energy about her. I guessed her age at about 28.

She also had a guitar with her. This fact might not seem like a big deal, but I’m always mysteriously more attracted to women who have some musical talent.

I was, at the time, trying to hitchhike my way back to Halifax after having my money stolen from me in Vancouver and working a week as a laborer in Calgary. I had experienced a lot in the month I was gone, but I was ready to head home.

I told her my story and without giving it a thought she offered me a ride to Toronto, a whole three days away. She had all of her things from her home in Boulder, Colorado in the back of her station wagon for her big move to Toronto. “Are you sure? I mean, that’s a long time to be in a car with someone you don’t know…” I said, being hesitant to put her in a situation where she felt obligated to drive me.

We eventually agreed that she would drive me to Winnipeg, drop me off somewhere for the night, and whether she wanted to pick me up again the next morning was up to her, no hard feelings.

That night we went out and explored the bustling city of Regina and found… nothing. No live music, no night life, just good conversation and a quiet beer together back in the kitchen at the hostel. Chana played a song she wrote on her guitar – the chords were simple, but the lyrics suggested she had experienced more than her youthful face showed.

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Hitchhiking Canada, Age 20. Part 2: The $50 Bowjob Question

Last we left him, our hero had accepted a ride in northern New Brunswick, with a 50-something truck driver named Ed , on his way north of Toronto.

Ed looked like your typical older truck driver. Three days worth of stubble, 50 pounds overweight, and a plaid shirt and trucker hat. Ed and I talked about all the usual topics for a few hours, and exchanged travel stories. I find that people usually like to reminisce about the old days when they used to hitchhike themselves. Ed told me about his first hitchhiking trip when he was seventeen in Newfoundland:

“My mom sent me down to the store to get some smokes, eh. An my buddy jus’ so happen to be standing ‘ere in front of the store with a big ol’ bottle o’ screech. An’ so we get to drinkin’ an’ — it seems like a good idea at the time, yaknow — and we decide to go for a hitchhikin’.”

“Well, I guess we got a little too into the booze, ’cause I can’t remember actually leavin’ the island, or even the people that woulda picked up a couple o’ drunk kids like us, but when I woke up… When I woke up it was a week and a half later and I was in Edmonton. I guess we had quite the bender! And the hotel room was all smashed up, and a girl was passed out on the floor with my buddy… And I tried, really tried to remember what had happened and how we had got to Edmonton, but I could only get bits and pieces, eh.”

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Upon Meeting The 100% Perfect Moncton Girl

No money, no ATM card — definitely no credit card. That was what I had decided for the trip. I felt like I needed the challenge. Hitchhiking to Montreal every couple of weeks was starting to feel routine. The adventure was wearing off a little. I decided I would bring only my guitar and clothes. If I was going to eat, I had to play my guitar – busk – for it.

I was hitchhiking to Montreal, but I left so late the first day I only made it to Moncton, a two hour drive away.

It was about seven p.m. when I got dropped off in Moncton. I walked down Main Street to an underpass, where the down town seemed to fade into residential, then back to where I started — the restaurant with the big lobster in front. There wasn’t much going on in this town. It looked like it might be a difficult night to busk, and I thought about the possibility of a hungry night without dinner. Was it a bad idea not to bring money? I was starting to doubt my adventurous side.

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Hitchhiking Canada, Age 20. Part 1: Drop out of College

I was 20, and had enrolled for my third year of university in Halifax. I didn’t want to go back to school. I felt I was spending a lot of money for an arbitrary piece of paper that I wasn’t sure I really needed. I also had a sneaking suspicion that after all the nights hanging out in bars with classmates, all the lounging around in study halls and great discussions of politics, world issues and women we thought were hot, that I was somehow insulated from “real learning,” although I had no idea what that meant at the time.

On the last day to withdraw from classes without financial penalty, I cracked. At 4:45, fifteen minutes before they closed, I ran to the financial office and “de-registered” for all my classes, and got a full refund.

Fuck it, I thought. I’m finished with classrooms. I want real, tangible experience. I’m going to hitchhike to Montreal (yes, there was a girl there…).

The next day I told my concerned parents I was a college dropout, and that I was getting a ride with a friend to Moncton (a two hour drive from Halifax) to clear my head and figure out what my long-term plans were. (My real destination, Montreal, was a 12-14 straight drive. At this point in my life, I didn’t feel like I could tell my parents about what I was really doing, as the
dropping out thing seemed to affect them enough)

Although fate would have nothing of Montreal, while in northern New Brunswick, I got a ride from a truck driver who was heading all the way to just north of Toronto — an offer I couldn’t turn down (as an aside, I actually don’t believe in fate in day to day life — I feel that we are all 100% responsible for our own actions and circumstances, but the appeal of hitchhiking for me has always been that your trip is very dependent on the people that pick you up, hence I believe in a kind of hitchhiker “fate”).

(to be continued…)