How I Started Long Distance Adventure Cycling

When I was 21, I worked in a nightclub of ill repute. The windows were painted black, and the doors opened into a dark haze of thumping music and hot bodies. No women worked there — we were all called “girls.” My uniform included fake eyelashes, spindly heels, and a smile that never faltered. Men seemed to really enjoy that version of me, and I went home each night with fistfuls of cash.

At first, the work was kind of exciting. I was an Honors student finishing degrees in Philosophy and Sociology, and the transgression of dark places fascinated me. I wanted to understand the nooks and crannies of humane intimacy. I thought of myself as a researcher, removed in some way from my own experience. But after a while, I learned: we never get to observe life from a distance. We are always here, always a part of it, and this matters.

Eventually, the dark and fascinating club became my real–and really depressing– life. My job was to let men leer at me, to be skinny and delicate, to laugh at my own lack of boundaries. I kept telling myself it was an acting gig. But as I took the last of my university finals, I found myself writing the same Annie Dillard quote over and over in my notebook: How we spend our days is, of course, how we spend our lives. I was making great money but losing myself. 

I remember the feeling I had on the night I finally quit. It was like I had been crushed into a smaller and smaller space that I didn’t know how to get out of. Everything was wrong, and I felt desperate. 

I needed a change, a new sense of self, the freedom to move differently. I drove back to my apartment and opened my laptop. All I could think was go, go, go. 

I scrolled through discount airline tickets to countries across the globe. Every new destination made my heart beat a little faster. Eventually, the thought slid its way into my brain:  I could. I could actually just go. 

Then it popped up on the screen — a cheap round-trip ticket to Iceland, leaving the following weekend and returning a month later. Click. I knew nothing about Iceland. Purchase. I was going. I sat back and stared at the screen. Did I really do that?  I started to laugh. The crushing feeling evaporated, and everything was suddenly, hilariously, possible again. 

The next day I started packing up my apartment and tried to figure out what in the world I was going to do in Iceland. I looked at a map and saw a single road, the 828-mile Ring Road, winding around the whole country. I had a bike and I’d once ridden about twenty miles on a bike path. Maybe I could bike around Iceland?

I had one week to get ready.

I went to a local bike shop and explained my situation. The woman behind the counter smiled and asked me to clarify.

“Have you ever toured before?” she asked.

“Well, no.”

“How many miles a day and days per week will you bike?”

“Hmmm … I don't know … ”

“What’s your budget?”

“As low as possible?”

“And when do you leave?”

“In five days.”

We both shrugged and chuckled nervously. Then she sold me a pair of basic panniers, a repair kit, and a bike box. Apparently, I had to put my bike in a box to get it on the plane–wow!  Clearly, there were a lot of things I had not considered. Actually, all of the things were the things I had not considered. 

Luckily, my dad had a friend named Dave who was an avid cyclist, and he sprung into action to help me get ready. We practiced oiling the bike chain, tightening bolts, and changing a tire. He showed me how to undo the pedals and handlebars and pack everything into my bike box. 

I’d never used bike tools before. The thought that I’d have to rebuild the bike — a mostly indecipherable mass of metal thingamabobs — by myself in Iceland was overwhelming. This was in the early 2000s: no smartphones, no google, no help. At the same time, it gave the trip the very edge I was looking for. I needed a change and a challenge. If I could just get myself into motion, I figured I could deal with the rest as it came. 

Over the next few days, I moved my belongings into my parents’ basement and crammed my camping gear into my new panniers. I packed clothes that would keep me warm and dry, as well as a tent, sleeping bag, and basic medical supplies. I planned to camp each night in the wild and buy food at grocery stores along the way.

I read that Iceland didn’t have any predatory or poisonous animals, and that there were twice as many sheep as people. Also, there were puffins! In the days leading up to the trip, fantasies of being surrounded by friendly woolly sheep and wild birds carried me through my anxiety.

I’d never been bike touring before, so I had no context for what challenges awaited. I searched online for references to cycling Iceland and found various opinions. The terrain is not mountainous, which makes it easier, but the winds are fierce, which makes it harder. Summer temperatures are cool and pleasant, but you might also get a lot of rain. The Ring Road cuts across stunning, remote landscapes, but that means no bike shops for hundreds of miles. I had no idea how to judge any of these factors. But other people were obviously cycling there, so why not me?

One of the things I’ve grown to appreciate about personal desperation is the infinity that it holds. We all have times in our lives when we become stuck, when motion stagnates and habits betray us. The things we thought would be good for us no longer are. We are busy but unhappy. The wheels keep spinning but we stay in the same place. This seeming lack of motion actually holds its own energy, like a spring that coils deeper and deeper into itself, just waiting to propel us forward. All we have to do is set ourselves loose.

Finally, everything was as ready as it was going to be. That weekend, instead of going back to my job at the nightclub, I boarded a flight to Keflavik. I don’t remember much about the plane ride itself. Perhaps I smiled and waved goodbye to all the drunk dudes I’d never have to see again. Toodleoo, boys. 

What I do remember–very clearly–is the feeling I had when the plane finally landed in the wee hours of dawn. It was the feeling of being myself but living someone else’s life. Everything was terrifying but in the most sparkling way. 

I found my bike box in the baggage claim and took out the bike pieces. Somehow I put all the thingamabobs back together and strapped on my panniers. I stuffed the box in a garbage can and rolled the bike to the airport exit. Outside was Iceland, cool and blue in the arctic dawn! I got on the bike and rode toward whatever adventure awaited. 

A version of this story was first published at The Adventure Cycling Association on August 14, 2019.