My dad dropped me off on the shoulder of an entrance ramp to I-90 on a sunny summer day in 1984 (hitchhiking on the Interstate is illegal, but it’s legal to stick your thumb out for a ride if you do it on the entrance ramp). I slid my oversized, kind-of-goofy yellow backpack out of the back seat of the family VW Rabbit and stuck out my thumb. I wore tennis shoes, jeans, and a hospital scrubs shirt. My hair was cut newly s...

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 tr...

I met some nice folks at the State Park. An older couple (probably about the age I am now) staying in an RV in the next camping spot over shared some of their breakfast with me, and wished me luck. I walked out onto the highway. I got a ride right up to the Canadian border early the next morning. He stopped before we got there. “You aren’t carrying drugs or anything,” he asked me. “No, I promise.” I was being truthful. “O...

My rides dried up. I’d had pretty good hitching luck up to then, with only a few long stretches of waiting for cars. Now, the situation had changed. I had a big bloody scabby bruise on the side of my face, right up against my nose. It did not seem to be engendering a lot of trust in me with the many cars passing me by. I wasn’t feeling too mythic. It didn’t help that I’d left the comfort of the Trans-Canadian Highway, tra...

Writing that last bit has made me wonder how I handled my cigarette habit, which at the time was a pack a day. I was between towns for days at a time, how would I even buy them? I distinctly remember, mid-trip, buying a pack of Canadian cigarettes, and being shocked at how expensive they were, which tells me I wasn’t walking into town for smokes every night. I suddenly remember that before I left Minneapolis to begin the...

I must have been lonely. I have a distinct memory of sitting in a park, in where I think is Sudbury, Ontario, my back against the trunk of a large tree, listening to Bruce Springsteen. Specifically, I was listening to the end of “I’m on Fire” off Springsteen’s Born in the USA, and marveling at the plaintive high lonesome “woo-hoo-ooo” trailing off, as the narrator of the song expresses his longing for the girl, his desire...

I decided to take a bus for the last section of the journey. I knew that traffic in the New York City area would be crazed, and no place to try to hitch a ride. I’d had excellent luck hitching so far, perhaps due to the protection of Mishipeshu the cat/dragon, but I was no longer within his sphere of influence. Maybe it was the time to stop tempting fate. I’d heard of New Paltz and knew it was fairly close to New York Cit...