Here & There: Discovering Road Magic

Words and photos by Bennett Figueroa

After graduating college jobless and dissatisfied, I set out on a quest to ride my bike from Whitefish, Montana, to Seattle, Washington, and then down the coast to San Francisco, California. With no itinerary or timeline set in stone, all I wanted to do was pedal to places I hadn’t seen before. My goal was to see things up close and at my own pace rather than from a car window.

Living in Minneapolis, I was at the heart of a revolution sparked by the murder of George Floyd. I was frustrated with the state of the world around me; everybody was. An idea sparked one day, and I asked myself: what if I just rode my bike for a while? And not just on a day trip but for an indefinite period of time. I’d always wanted to see the Pacific Northwest, especially by bike, and I figured this could be my shot. Knowing I would probably never have the chance to pedal around the country for a few months again, I dreamed up a plan.

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At the time, I didn’t have much bikepacking experience besides the occasional overnighter. Looking back at the amount of gear I brought makes me cringe a little. I wanted to have a ready-for-anything rig with all the gear I’d need in the backcountry. I packed a giant solar panel, a Moka pot, a few changes of clothes, and a bunch of other junk I later shipped home. I bought a Bob Yak trailer on Craigslist and hose-clamped a rack to my fork. Since the trailer wouldn’t fit the 29-plus wheels on my Surly Krampus, I reached out to a family friend who welded an extension onto the trailer’s yoke. I was overpacked and overeager.

I made many mistakes in the beginning, like packing too much, not having a solid route to follow, and thinking I could do everything on my own. These things taught me that it’s okay not to always have the perfect plan. I learned a lot about how to take things as they come and also when to be strategic.

With my bike and all my gear packed, my family and I took a road trip out to Whitefish. There, I met up with a friend, and we spent a few days riding around the area, testing everything before the big ride started in earnest. I wanted to see how the trailer would perform on forest service roads and singletrack (it did surprisingly well). Eventually, we parted ways, and I was on my own. It was my first time being fully loaded down with everything, and I could feel the weight with every pedal stroke. Everything felt sluggish as I wasn’t used to pulling so much gear behind me. I was naive and hadn’t done a good test with everything loaded on the bike. Regardless, I slowly cranked ahead as tendonitis built in my knee and anxiety loomed in my gut.

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Those first few days on my own were possibly the hardest of the trip, both mentally and physically. Knowing I had hundreds of miles ahead of me was daunting.

It was mid-September and dry. Wildfires were raging further west of me, playing a significant role in my diminishing mental state. The skies were hazy, and the air smelled smoky, which made the thought of getting caught in a wildfire a difficult one to ignore. I was also trying to piece together a route on the fly that kept me on dirt roads, although this proved to be difficult. I was forced to ride a few sections of road that had next to no shoulder and were heavily trafficked by logging trucks. As each truck passed, it felt like a raging goliath narrowly squeezing by. My motivation to keep pedaling diminshed further and further as I feared for my safety.

When I reached Libby, Montana, I stopped to rest and reflect. I was tired, alone, anxious, and already feeling like a failure. It had been less than a week, and I was already regretting everything. I stopped at a small cafe knowing that coffee would help me think. I sat down outside with an espresso and tried to piece together my next move.

After a few hours, I saw someone roll down the street on a fully loaded touring rig. He saw my bike and pulled over to chat. This was when I met Doug, a dirtbag ex-climbing guide in his 50s who had been traveling by bike for the past several months, making a giant loop around the American West. He was tan and had a rough-and-tumble attitude. We chatted briefly about where we’d come from, where we were going, and some of our gear. It just felt good to talk to someone. It turns out he was headed to Seattle to see his brother. I mentioned to him that I wasn’t feeling great about moving forward, and he convinced me to get back on the saddle. We ended up riding out of town together that evening.

It was the start of our unexpected month-long journey together and my first taste of how quickly things can change for the better on the road. It’s something I like to call road (or trail) magic: serendipitous moments that surprise you while traveling.

Fast forward a few weeks, and Doug and I were fighting the winds in Eastern Washington. We enjoyed the endless golden prairies and rolling landscapes despite being slowed down by constant gusts. Each day offered something new and exciting. I was finally starting to feel a good rhythm in my legs. As the days and miles passed, the self-doubt and anxiety I felt earlier started to fade.

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It felt good to have someone like Doug to share the adventure with. He was a seasoned bikepacker/tourer and had lots of experience on the road. For an older guy, he could put the miles down too. Eventually, we made it to Seattle and had to part ways. We’d gone through a lot during the month we’d ridden together: sleeping in ditches, crossing a highway bridge over the Columbia River Gorge, climbing steep forest service roads, and occasionally stealth camping.

As I went on alone to ride the Olympic Peninsula, I felt reinvigorated. Moving forward, I found confidence in myself again. Although there were moments when I felt all alone, I thought back to all the people who supported me along the way. I would often think about Doug and all the things he taught me throughout our short time together. He knew how to live simply on the road and ride long days in the saddle. He told me stories of his bike tours through Canada, South America, and all over the United States. Working as a seasonal climbing guide for most of his life, he saved money to do trips like this during the off-season. He taught me how to find free water, navigate a complicated bike route, pack lighter, and find camping spots in a pinch. He had a sly intelligence and was street-smart. I still think of him often and wonder what adventure he is on now.

I rounded the Olympic Peninsula through the many microclimates of Washington. When I reached Oregon, I was greeted with the gnarliest overnight storm I’ve ever experienced. It came without mercy in the middle of the night and left me completely rained out. All of my gear was soaking wet after stupidly leaving my bags outside of the vestibule. In the morning, with little to no sleep, I packed up and checked into a hotel for a luxurious night of rest.

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The next few days provided good weather as I rode into the coastal town of Newport. Cruising in, I saw two others with loaded bikes stopped on the side of the road, fixing a wheel. I pulled over, said hello, and chatted for a while. Garrett and Nathan were headed down the coast like me. At that point, Garrett had ridden his bike from Michigan and had been on the road for several months. Nathan had originally started with Garrett, took some time off for a knee injury, and later rejoined him in Seattle. They were around my age—in their mid-20s—and traveled relatively light with a few panniers. That first day together, we rode like hell down the highway. I was stoked to pedal with people again. It was an instant friendship.

As I got to know them, I learned that we shared many of the same feelings about bikes, politics, and music, among other things. We were all from the Midwest, and it was our first time doing a grand tour by bike. I think we all had the same experience of growing up in the Midwest but wanting to see more of what the world had to offer. Riding full days felt easy together, and having someone to draft again was nice too. Despite my heavy-duty bike and 29+ tires, I kept up pretty well with their more road-friendly wheels. We traded off setting the pace and fed off of each other’s energy as we rolled south down the Pacific Coast Highway.

One of my favorite memories with the two of them was riding along the Avenue of the Giants, where we came across a small farm stand. We bought a few vegetables to cook later and asked the farmer if he knew a good spot to camp. He brought us to a beautiful patch of land not far off the road under new-growth Redwood trees and told us we could set up camp. That night, we sauteed our veggies in a heap of butter, which felt like a delicacy after consuming an endless stream of gas station hotdogs.

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When we reached the Bay Area, we stayed with Garrett’s cousin and spent a few days resting. A couple of friends were planning to meet me in San Francisco in a week’s time, so I decided to keep riding with Garret and Nathan to Santa Cruz. We spent our last few days together sharing meals, a few beers, and incredible views of the Pacific Coast. These were some of my favorite experiences during my time on the road. Riding next to the ocean at a bike’s pace was something special. We forged a great friendship along the way too. Eventually, I had to say a tough goodbye and ride back to San Francisco solo once again.

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On the bittersweet ride back, the excitement of seeing my friends and getting to bike around San Francisco helped me move forward. I’d always wanted to climb and bomb the steepest hills I could find on my bike. One of the cool parts about riding in different cities across the US is feeling how each one flows. With over a thousand miles under my legs, I enjoyed charging up the notoriously steep streets and finding lines around the city.

After San Francisco, it was effectively the end of my tour. I hitched a series of car rides from friends and spent a few weeks on the road. During that time, I rode a large portion of Highway 50, rock climbed in Utah’s Indian Creek, and completed the White Rim Trail with a few friends. Feeling tired and dirty, I missed home. I was luckily able to hitch a ride back to Minnesota with a friend who let me cram my bike and trailer into the little space left in his Toyota wagon.

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The adjustment was hard when I got home to Minnesota. It was good to see family and friends, but there was a feeling deep down I couldn’t shake. I missed living on the road by the pace of a bike—not too fast, not too slow. I missed the ocean, sipping coffee at camp, making new friends, the warm sun on my tent, and all the kind people I met along the way. Looking back, I learned a lot about being independent and being okay with asking for help. I experienced some of the lowest lows but also the highest highs. I almost quit in the beginning, but with a little help and some road magic, I realized what I was truly capable of.

With all the photos I had taken along the way, I made a photography zine called here & there. It’s a glimpse into the various places I got to see through the power of a bike and friends. As a graphic designer and photographer, making print work is a valuable way I use to share my adventures on the saddle. Find a little peek at it below.

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Further Reading

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