By “WanderN Wayne” Hammerstrom

He was drinking a beer, while driving.

This first ride on a hitchhiking adventure from Oregon to my home in Wisconsin was making me quite uncomfortable, if not also presenting unanticipated danger.

What a crazy impulse, to hitchhike over 2,000 miles. But what choice did I have? My summer job as an assistant leader with Outward Bound had ended in August. I hadn’t earned enough to consider flying or taking a bus.

Outward Bound Schools are an international program teaching wilderness survival. I’d spent three months in the mountains of Oregon teaching older teens an outdoor curriculum of wilderness hiking, mountain climbing, cliff repelling, and how to endure a 3-day solo retreat beside a mountain stream. We created experiences to “maximize apparent danger with a minimal actual risk.” We wanted them to embrace the words of Alfred Lord Tennyson: “To strive, to seek, to find, and not to yield.”

“3-Finger Jack” in the Cascade region of Oregon

My beer-drinking driver let me out near Portland, Oregon. The Interstate route towards home was clearly eastward now, but I still had to get other drivers to pick me up. In the summer of 1968, hefting a large pack on your back may have conveyed to others that you were a draft dodger, a wily vagabond, even a homeless person of questionable intentions. I was none of these, but first impressions count when thumbing rides. I tried to look presentable: young, clean and not desperate. These traits, of course, fatigued after long lengths of time waiting for kindness to stop and give you a lift. That is, a ride to some distant destination.

Three young airmen picked me up somewhere on America’s rocky spine in Oregon. They were returning to their Air Force base adjacent to Mountain Home, Idaho. To hitchhike is to travel by obtaining free rides from passing vehicles. Thus, hitching a ride removes choice from your options; drivers select you, not you them. Daisy-chaining a succession of rides as a passenger means you lose some control as to when you might eat, sleep, or use a restroom. Luckily, I was about the same age as these guys. We passed over miles of highway talking about cars, girls, and sports. Before dropping me off outside their base entrance, they even bought me lunch, a last taste of hitchhiker’s good luck for a while.

My next state, Wyoming, was the worst place to catch a ride. In a state with few people, no one wants to remain long in its wind abraded landscape. Cold winds of the western highlands chilled me as cars flew past. My extended arm was as useless as the motionless arm of an abandoned oil pump. I stood outside a highway restaurant. Brazenly, I asked people as they exited if I could have a ride anywhere east of this place. No one accepted my plea. Walking back to the highway, I waited hours, hoping for my next ride.

The request was unusual and possibly conditional. He’d drive me as far as central Iowa. Would I be willing to help pay for gas and occasionally drive? Hell, yes! Foreign born, he didn’t talk much as we tag-teamed driving and sleeping. He told me I was hitchhiking poorly by standing on highway shoulders. At his suggestion, I made a sign, “Need Ride East,” to hold up to a side window whenever we passed a vehicle with license plates of a state east of the Mississippi River. I got a nibble from a driver of a van with Illinois license plates. Our vehicles slowed together to a stop on the highway shoulder.

My transfer to the van came easily, though I was shocked to see that the driver was a mother traveling alone with her two young daughters. Any possible threat I might have displayed vanished quickly when I fell into a deep sleep, remaining oblivious to motion, sounds, and where I was. Her family lived in Highland Park, a wealthy residential community north of Chicago. This ride alleviated all worry I had about how I would hitchhike around or through Chicago.

I spent the night in the dormer of their home after meeting her husband when we arrived in darkness after midnight. As a guest I would be taken back to the highway following breakfast the next morning.

Too excited by my nearness to home, I awoke before my host family and quietly explored downstairs. In a corner of the huge living room rested a grand piano. Centered between a couch and sitting chairs was a large circular table covered with stacks of social and political magazines, books, and papers. Surrounding me and the contents of this room were walls of hewn logs. I had spent the night in a log home.

My overnight happened only a week following the riotous 1968 Democratic Party Convention in downtown Chicago. My host family was politically active, and they provided lodging for several of the protestors. Contentious discussions had been held nightly around the table I now stood next to. During my breakfast with the family, conversation covered similar topics of government, military, social and moral arguments; although my comments were weakly positioned compared to theirs.

A last ride to my parent’s home came from a man who was one of “Shirley’s boys.” I knew him from a group of men who dined every Friday with Shirley, a waitress in the restaurant where my mother and I also worked. Opening the door at home completed my hitchhiker’s journey from a tent in Oregon 2,000 miles away.

I never hitched a ride again after this adventure. Maybe it was some of the frustrations I had, or the uncertainty of waiting alongside busy highways, or never knowing what the driver might be like.

Of course, these are the experiences that made my hitchhiking a storied memory. Each ride carried me over varied landscapes, mile by mile, inspiring my sense of places with wonder. Shared stories during hours of riding together drew me from the expansive outdoors to interior lives of people I hadn’t known.

Because of my decision to hitchhike cross-country, my life was enriched through the random kindness of traveling with strangers.

© 2019 Wayne Hammerstrom

Wayne Hammerstrom (WanderNWayne) lives in Madison, Wisconsin. He wanders through life as a verb, many times directionless in travel and becoming.