Days 99-101 – 10/13-10/15 – The Dalles to Portland, OR – 101 miles

The sun burst over the Eastern Gorge, the Columbia River glittering below, as the hills were cast in a soft, pink hue. An early departure from The Dalles saw me climbing steadily into the hills, accompanied by a resurgent urgency. Only two stages–admittedly, two long stages–stood between Portland’s eastern fringe and me. A much shorter third stage would deliver me home.

I climbed to the short summit on Seven Mile Hill Road, leaving those views behind, and then transitioned immediately into the descent to Mosier, passing through a series of peach and apple orchards. The sounds of Mosier Creek Falls announced my entry into town, and soon after I was in Mosier’s tiny center, still sleepy at this early hour. All around me, the leaves were turning, some falling crisp and yellow to the road, while a few people strolled home with hot drinks from the coffee shop. An idyllic Sunday morning in the Gorge.

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Soon after I crossed the border into Oregon, a man saw me walking through Nyssa and asked where I was coming from. He quickly fell into storytelling mode, rattling off memories of hitching his way around the country, before transitioning to his thoughts about the current state of affairs in Portland. “Just be careful when you get there. It’s filled with dangerous people.”

Portland’s national reputation took a hit over the last handful of years, with the protests and riots following George Floyd’s murder drawing widespread attention. Even when the riots were at their worst, of course, their impact was highly localized, but that still shaped a perception of the whole city being aflame, the population imperiled. That was followed by a significant uptick in the homicide rate during COVID–something that happened to varying degrees across the country. (And, as has also happened elsewhere, that rate has subsequently declined.)

On Monday afternoon, I crossed the Stark Street Bridge over the Sandy River, currently closed to vehicle traffic, and entered Greater Portland. My plan from there was simple enough, taking Stark Street through Troutdale, and then following Burnside Road through Gresham and onto Portland on Tuesday morning. Portland is broken into four quadrants–NW, SW, SE, and NE–and Burnside is the line between north and south, leading all the way to the Beaverton line on the west side. It was the natural conduit for my trans-urban walk.

Block by block, the city gradually took shape. I looped high on the hill overlooking the Sandy, passing large estates, and then, as Stark straightened, the houses became more modest and compact. Students collaborated under tree cover outside Mount Hood Community College, and then a small commercial center advertised its new pickleball courts. I saw a Thai restaurant. And then another. And another.

Urban congestion kicked into another gear after I turned onto Burnside, the road bisected by the MAX line linking Gresham and Hillsboro. I passed taquerias and mercados, and gradually the foot traffic around me increased. Despite being, on paper, one of the more dangerous parts of the city, based on homicide and assault rates, all seemed peaceful and placid. Just regular people, going about their lives, untroubled. It’s not to say that the statistics are incorrect–though certainly our perception of the statistics often is. But when you’re not here, present, feet on the ground, it’s far too easy to extrapolate that the sky is falling from a couple of raindrops.

Late in the afternoon, I crossed the road to the MAX station and bought a ticket. While there’s certainly no shortage of tents pitched around Portland, I wouldn’t be adding mine to the mix. I had a bed waiting for me, waiting for three and a half months now. I was close enough.

As I stood at the MAX station, I looked down at a circle of folks, hunched together and watching as one of their members tore up strips of aluminum foil, with some other materials sitting to the side. A sight that has become far too common on MAX trips for me in recent years.

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From Mosier, I enjoyed a gentle ascent, first following a footpath through the trees, and then joining the Historic Columbia River Highway Trail. On this sunny, Sunday morning, the locals were out in force, riding and jogging and rollerblading along the broad asphalt track. I paused at a viewpoint, looking northward across the Columbia into Washington, and I realized that somewhere in the past handful of miles, I had finally crossed into the Pacific Northwest. Folks in points eastward might take umbrage with that characterization, asserting equal claim to that PNW label, and that’s fair. But this was quintessential Pacific Northwest–an explosion of green, with Douglas Fir and Cedar trees gradually taking preeminence over the Maple and Alder. Rolling hills were replaced by more dramatic mountain peaks. Somehow, the Columbia became bluer in the midst of all that verdant foliage, disrupted only by craggy protrusions of rock.

A sharp descent into Hood River provided the lone interruption to that stunning scenery, with its manicured Main Street offering coffee shops, breweries, and boutique wineries, all packed with weekenders savoring the day. I wanted none of it. The mountains were out there, beyond the city limits, so I powered on, undeterred.

Following a route interruption, still waiting on a final developmental push, the Historic Columbia River Highway Trail resumed shortly before Viento State Park. Immersed in thick tree cover, I began another extended ascent, pausing briefly along the way to make short detours to see Starvation Creek Falls and Hole-in-the-Wall Falls.

When I finally arrived in Cascade Locks, my destination for the day, the southern terminus of the Bridge of the Gods, and a key stop on the Pacific Crest Trail, I was exhilarated, feeling the deep satisfaction of a walk in the woods, the joy of being home. Why would anyone choose to live anywhere else? I realize there are damn fine answers to that question, but I still can’t fully wrap my mind around it.

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By 7am on Tuesday morning, I was back in Gresham, pushing westward into Portland. The night weighed heavily on many of the folks on Burnside. I passed a woman who stood facing a door, her body contorted at a 90-degree angle, as though she were trying to peer through the lock. A man slept on the sidewalk in a sleeping bag, damp from the steady rain, with only a pair of tree branches offering the most meager of cover. A man urinated on a doorway. A few kids walked to school.

I crossed I205 and gradually the neighborhood shifted. Stately, elegant, historic homes suddenly flanked Burnside, as I entered Laurelhurst. Well-dressed people walked their dogs, looking more at their phones than where they were headed. Teenagers hugged each other as they met at Starbucks. More coffee shops followed, as did classical hippos and a climbing gym and a staggeringly garish building at the confluence of Burnside and Couch. And then I was on the bridge, crossing the Willamette River into the Westside, the Pearl, Old Town.

No sooner was I in the heart of Portland than I was confronted with its tragedy in its fullest form. Tents lined the sidewalks. Perhaps 40 people lined up outside a mission. Some made sudden, jerking, twitchy motions, arms swinging wildly. Others had faces etched with despair or grief or pain. Still others didn’t look that different from me, tracking everything unfolding around them with cautious attentiveness. On the street corner, I took note of what looked like an explosion of torn clothing and garbage, centered around a small mound. And then I realized that mound was a person, bent and curled at impossible angles, a small hand clutching half a cigarette protruding ever so slightly from the wet fabric. One block after another, the sidewalks were lined with trash and waste and wreckage.

Years into this crisis, we still have no answers. Nothing has changed.

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Travel Portland couldn’t ask for a better advertisement for the region than what Monday morning offered. After a couple hours spent in total darkness, continuing along the Historic Columbia River Highway as it wound around I84, the sun rose and I powered past Bonneville Dam and Ainsworth State Park. Horsetail Falls provided the opening act before getting off stage for the headliner, Multnomah Falls. I bought my most expensive coffee of the trip and then sat down on a bench overlooking the two-part waterfall, as one couple after another passed by, posing for pictures.

The highlights kept coming. Wahkeena Falls. Bridal Veil Falls. Shepperd’s Dell. And in the meantime, I was accelerating, adrenaline coursing through my veins, driven ever faster as the ascent grew and auto traffic on the historic highway grew. With practically no shoulder and limited visibility, I took to walking right down the middle of the road, my head on a swivel, swinging back and forth from one lane to the other as cars approached. It was oddly exciting, like a video game. And finally, the tree cover thinned, the Columbia broke through, and an old stone structure towered overhead. The Vista House, built as a rest stop for travelers in 1917, at one of the most beautiful spots in the state, is still there, doing its job today.

Before too long, the descent began, leading me through Corbett and then–quite a bit later–to the Stark Street Bridge over the Sandy River. It’s impossible to argue. This is one of the most beautiful places on earth. How could anyone deny it?

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After seven or eight blocks, I moved past the densest concentration of homeless folks, and while there were plenty of reminders afterward, the city gradually took on a more tourist-friendly face. Powell’s Books, as marvelous as ever, announced the transition. As Burnside took to the hills, I shifted onto a footpath into Washington Park, climbing into the Rose Garden and then joining the Wildwood Trail through Forest Park and the Arboretum.

My route led me through one home, my old school, and then onto my actual home, back for the second time in 24 hours, after so many days away. And the beauty of those final miles, combined with the joy of arrival, was enough to tamp down any lingering unease over Portland’s greater challenges.

And yet, those can’t be escaped entirely. Portland’s reputation precedes it; it certainly preceded me. Anytime I introduced myself to folks on this walk, and mentioned that I was from Portland, Oregon, they leapt to certain conclusions about me. They certainly had conclusions well formed about my home. And while some of those were entirely unfair, the product of the rightwing media’s hysteria and outrage machine, we have also earned some of them.

Portland could be a progressive city on a hill, a vision of the kind of world liberal politics can create. We’ve lived through a boom time, when the city has been thriving economically, providing ample resources. We had, for a while, a rare kind of political consensus, especially in the realm of certain social justice beliefs. Nowhere did this show up more prominently than in the city’s response to the ill-conceived and worse-executed War on Drugs, resulting in a popular movement in favor of decriminalization policies. Unfortunately, those policies didn’t just fail, they backfired. The pendulum is swinging back. It’s recriminalization time.

When Portland fails, progressivism fails. The arguments in favor of decriminalization are invalidated, tarnished by the lingering images left in everyone’s minds following these past years. Is our political homogeneity an opportunity or a weakness? Is the lack of ideological diversity resulting in policies that haven’t been suitably challenged and tempered through disagreement and compromise? Or do we lack the capacity to develop sufficiently nuanced strategies to combat complex, systemic problems, opting instead for simple, accessible policies that win the headlines and feel good?

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