Despite the ignominious ending of my previous trip, I was determined to try it again, with a few key differences.

One: Note that my Dad was leaving me on the shoulder of I-90, not I-35. I was heading north, not east. I had decided to hitchhike to New York City via Canada, swinging over the top of the Great Lakes before dropping down into the US near Champlain.

Two: I would be travelling alone.

Three: This was a one-way trip. I was hitch-hiking to New York City in order to live there. I wanted to write and direct theatrical plays, and New York City seemed like the best place to do so.

As I look at maps of the Great Lakes on the Internet, my plans of over forty years ago come swimming hazily back, and I realize with a start that perhaps I was not quite as reckless and wild as I was assuming myself to be.

What leads me to this conclusion?

The realization that on the Canadian side of the Great Lakes, there are campgrounds everywhere, literally dotting the map I am looking at. I look closer, and read the fine print that no camping is allowed within 200 feet of the lakes, but as long as you are not trespassing on private property, camping was legal. (disclaimer: this isn’t true anymore).

My true reasoning for taking this route becomes clear: I would always have a place to sleep. One of the great dangers during that first hitchhike to New York City was having no place to sleep. We slept in the cars we were hitching in. We tried to take care that one of us was always awake, but in practice I’m not so sure we did.

It becomes more clear to me why I’d packed my tent and sleeping bag and campstove. It wasn’t in case of emergencies. It was my plan. I’d camp along the Great Lakes for the entirety of the trip.

I wish I had that old Rand-McNally map I used to find my way. I have a vague recollection of marking in advance the places I intended to stay, in yellow highlights. I expected the trip to take to weeks, and it did. Perhaps that 22-year-old kid was not quite as stupid as I’ve been assuming.         

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Here’s another detail that improved my trip immensely, though I didn’t know it at the time: Canadians are really nice! Specifically, they don’t consider hitchhiking to be dangerous, for either the hitchhiker or the drive picking them up. Hitchhiking seems to have been normalized. (Again I’m talking about the Canada of forty years ago; don’t try this at home.)

There was an almost wholesome vibe about it, once I’d crossed the border. Families picked me up. Teachers picked me up. I wasn’t hiding for police, I wasn’t attempting to look clean-cut and non-threatening. I could relax.     

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Not knowing I wouldn’t have to appear clean-cut, I got a very short haircut before I left. I got it not only to appeal to drivers picking me up, but also to have a no-maintenance haircut.

I started in Ankeny, Iowa. My first stop was Minneapolis, the city I’d lived in for four years before deciding to move to New York City. I went to a bar on the University of Minnesota’s West Bank with my buddies John Metcalf and Peter Dodge. Later, John and I ended up at a late showing of the just-released Purple Rain in downtown Minneapolis (which marks the moment in time as July 1984). I ended up spending the night with a girl who lived upstairs from John.

I left for New York City the next morning, heading north on I-35. Hours later I arrived at the terminus of the Interstate in Duluth. I stopped at a diner there, sitting down in a booth, my gigantic pack next to me.

A girl (I was just a kid, but she was clearly young, younger than me) slipped into the other side of the booth, facing me. She’d been sitting with her friend at another booth. Forty years ago, but I remember her opening monologue pretty well.

“I saw you hitchhiking outside and I said, ‘Whoa,’ and then I watched you walk in with your pack and I said, ‘Double whoa.’ Are you a hitchhiker?”

“I am.”

“Where are you going?”

“New York City.”

“Whoa.”

“I’m going through Canada.”

“Double woah.”

She was fond of that particular couplet. I don’t think she was trying to pick me up. I pondered the possibility at the time, and it seemed more likely she was testing her freedom, and perhaps her flirting skills, in a safe place, with a friend nearby. I had no interest in flirting back, or in a romantic encounter, but I confess it did wonders for my ego. In my own head, there was a mythic aspect to the trip I was taking. It was one thing to move to New York City by buying a ticket and taking a plane there. Anyone can do that. But to first wander into the wilderness of Canada, spend two weeks or so making my way around the shores of the Great Lakes, and then emerge from the wilderness into the glass and metal canyons of the streets of New York: that made the trip appear to be the journey of a hero, just like Joseph Campbell talked about on PBS. New York was the Emerald City.

I didn’t tell her any of this of course. This was all in my head, and at the time I probably couldn’t have even verbalized it well. But it felt good to see someone else react to the mythic figure I thought I was cutting at the time. I politely answered her questions, and was careful not to flirt lest I lead her on. She scooted out of the booth a few minutes later, wished me luck, and returned to her friend.

I ate lunch and hit the road. But I’d learned my first rule for the trip: don’t talk overly about myself. Specifically, don’t tell people I was hitchhiking to New York City, and certainly not the part about making the trip via Canada, because it instantly turned any conversation into a conversation about me. I was uninterested in me, and wanted to know more about other people.   

I-35 ended at my feet. Highway 61 began at precisely the same spot, and hugged the coast of Lake Superior. I stuck out my thumb. Hitchhiking is legal on both Minnesotan and Canadian highways.

I didn’t get to the US-Canadian border that day. Letting Google Maps be a surrogate for my paper Rand-McNally road atlas, I can see where I probably would have camped that night, knowing my plan was to camp in State parks (and in Canada, Provencial parks). There are only two possibilities: Gooseberry Falls State Park and Split Rock Lighthouse State Park. Since I don’t remember seeing a lighthouse, I’m going to assume I stayed at Gooseberry Falls (though I don’t remember seeing gooseberries or falls either).

I also note that, according to my modern map, at some point I passed through a place called Castle Danger. That place name would have set my imagination spinning if I’d encountered it, both for the literal name and for its close relation to “Chapel Perilous,” a term I was already familiar with due to Robert Anton Wilson’s Cosmic Trigger, a book that influenced me heavily at the time.       

“Everything you fear is waiting with slavering jaws in Chapel Perilous, but if you are armed with the wand of intuition, the cup of sympathy, the sword of reason and the pentacle of valor, you will find there (the legends say) the Medicine of Metals, the Elixir of Life, the Philosopher’s Stone, True Wisdom and Perfect Happiness.”

- Robert Anton Wilson, Cosmic Trigger