The Oregon Trail, 175 years later — Gravel Bikes, Running Shoes & Great Brews & Views

Oregon Trail


Farewell Bend State Park is where travelers left the Snake River and headed northwest.

written by Kevin Max

Oregon gives a lot and sometimes, when you’re retracing the Oregon Trail on bike and on foot in a four-day span, it gives more than you expect. Okay, we took an Airstream too, but chiefly for its historic connection along the Oregon Trail. Read on.

It was the second week of June, and my friend Zach Violett and I left Central Oregon with our dogs and a thirst for new adventures and good beer, bound for Farewell Bend State Park—the eastern point of modern-day Oregon’s section of the Oregon Trail. Wagons that left Independence, Missouri, crossed here months later into what is now Oregon. We brought gravel bikes, running shoes and a curiosity of what we might find along the way.

Zach is an ultra runner who was recovering from a hernia surgery. Thus predisposed, he would, by doctor’s order, have to reduce his mileage by multiples, which made him compatible with my maximum effort. Slumming, really. 

Morning broke at Farewell Bend State Park. This section of Oregon lies within Mountain Time. We had already lost an hour and the day was getting hot. I don’t remember why I agreed to a wild boar breakfast burrito before getting on my bike, but you do what you must to survive out here.

Barley Brown’s in Baker City produces award-winning beers.

I thought we’d be pedaling rural paved roads and for no more than a few hours in a loop that included the Old Oregon Trail. Honestly though, I’m not an accomplished mappist. I prefer getting lost and letting things happen. 

Zach has the mapping gene, but no true sense of scale. You can see why this combination often leads to desperation. Map distances seem much more feasible in inches than mountain miles. What could go wrong? Our ancestors didn’t have Lycra and tubeless tires. They had denim and ox-pulled wagons. 

Last time I went on an expedition with Zach was two years prior. We were with a group camping on the Umpqua River and decided to head out on a quick sightseeing ride just before dinner. We rode back into camp in time for lunch the next day after committing to the wrong side of the mountain and ending up 50 miles away in Oakridge with no cell service. 

I had forgotten all that until we hit the sign “Primitive Road Next 22 Miles.” Over the next four hours, and what turned into 35 miles, we rode over dirt roads that wound and climbed and descended through some of the most stark and beautiful country. It was indeed the Old Oregon Trail, but not what I had expected. The paved roads from my expectations became a gravel road winding south and west of Farewell Bend State Park that looped back through dry ranchland. The temperature climbed into the 90s and our water supply was inferior to the heated effort. The ground alternated between packed gravel, where you could get up to speed, and sharp, rocky terrain where your hands and jaws clenched in a downhill clatter. 

Cows behaved oddly when they saw us on bikes. Some scampered uphill and beyond our reach, just to be sure. We were neither conquerors nor butchers, just half-crazed passersby. Likely the only humans they’d ever seen had arrived on four wheels and in pickup truck shapes. 

At one point, I found my wheels above me, my feet still clipped in and the soles sunny-side up, with Zach far ahead. Lying on my rocky bed yet unwounded and in no particular hurry, I took out my camera and snapped a photo to record the absurdity of it all. Even at 175, the Oregon Trail still gave you hell. 

At this arid point along the Oregon Trail, the verdant farmland of the Oregon Territory must have seemed a lifetime away for weary emigrants. After two flats perpetuated by goatheads—thorny barbed landmines that thrive on desert gravel—we rode back into camp, eager for the civilization of Baker City. 


Baker City

Baker City is a lovely outpost along the Oregon Trail. Its history has been well preserved in its handsome downtown buildings. While posing as a turn-of-the century movie set, Baker City is also bubbling with new life and nostalgia. 

Among other things, Baker City was the founding home of the modern-day Airstream. A young shepherd named Wally Byam sought a better-wheeled shelter for his cold nights. Eventually, that experience led him to build the first Airstream travel trailer. A nation of rugged explorers, clad in silver and riveted throughout, took to our roads.

We found a berth for the Airstream in front of a Methodist church in downtown Baker City. Bless all 38 feet of this truck and trailer. We took the dogs for a walk through neighborhoods with historic Victorian homes. Two blocks east on Main Street stood the Geiser Grand Hotel, another beautifully restored Victorian building with an airy two-story Palm Court, topped by a sprawling stained-glass ceiling. A little farther up Main Street, we found Barley Brown’s Brew Pub. 

Zach and I had first encountered Barley Brown’s en route to a hut-skiing expedition in the Wallowas in 2011. Since then, Barley Brown’s has opened a tasting room next door with more than twenty of its beers on tap, national awards hanging around the necks of many of them. 

I took to a hazy IPA, and Zach, a pint loaded for bear. Next to us were a couple who had moved from Portland to get away from it all. Their days are now spent more on bikes and trails, they said, than commuting in cars. In the early evening light, they had a healthy radiance about them and gave us local trail details.

A pint later, we ambled down Main Street to Latitude 45 Grille. The menu was a delight, with locally sourced meats and handmade pasta sauces. I had the baby back ribs with house made barbecue sauce. Zach went for pork Milanese in a cremini mushroom and brandy cream sauce.

The next morning was overcast and lightly raining. Main Street is also home to Lone Pine Cafe, the best little breakfast spot in town. Wide wood floorboards were aged and soft to the step. Where one era of bricks ended along the walls, another picked up fatter and lighter in color than its predecessor. On a Saturday morning, Lone Pine was the place to be.

Our friends from the night before had mentioned the little local museum nicknamed The Nat, for the 1920s natatorium building in which the Baker Heritage Museum is housed. I promised myself I wasn’t going to get bogged down in history on this trip and instead celebrate the outdoors, new beers and the avant garde—the updated Oregon Trail. But it was raining, and I was procrastinating before a long run.

The Nat was a true hidden gem, literally. Inside was a Smithsonian-quality collection of gems that could have been at the Museum of Natural History in New York. I was enamored with the old typeset printing press, whose word clusters—Allies Agree On, No Casualties Reported, and my favorite, Treat Them As Traitors—were cast in steel and last used during WWII.

Upstairs, we found a small case and display dedicated to Wally Byam. Photos showed the prolific traveler in Egypt and South Africa, leading Airstream caravans like columns of benevolent tanks through the countryside. A beret, corkscrew and bottle of Happy Camper wine with an Airstream label were also in the case.

While it was still raining, we packed up the Airstream and drove 6 miles northeast of town to the National Historic Oregon Trail Interpretive Center. The center sits on 500 acres at the top of a hill overlooking a vast valley, where wagons once crawled along the lower regions. The well-worn ruts of the twenty-six years of migration were still baked into the ground, a reminder of how young America is and of the relentless yearning for a better life.

This institution is an icon for the state and a foundational piece of Oregon history. Anyone driving in the vicinity owes it to themselves to stop in. What struck me most was the number of people who set out on the journey from Independence, Missouri, 175 years ago, and the support many of them received from Native Americans, unwitting of what it all could mean for their own future.

After a dose of solemnity and history, we emerged from the building and the rain had stopped. We put on our running shoes and ran off down the trail. Every June, the BLM organizes a Run to the Ruts 10K. We would retrace those footsteps a week later in perfect running conditions, cool and overcast.

We took our dogs and plummeted into the valley below, where a single wagon stood in the tracks as a symbol for all who passed this way. As we climbed back to the parking lot to end the run, the rain came again, as if permitting us that allotted time.

There were a few more stops for us along the Oregon Trail, but none so momentous as running in the ruts.



La Grande and The Dalles

We buzzed into La Grande for lunch and found another hidden gem in Side A Brewing, a new brewery set in a historic firehouse a block off La Grande’s Main Street. Good food from local ranches and farms were on the menu, as well as good local beer. We regretted not having more time to spend on another beer.

We drove west along I-84 with the fading western sun laying flat along the surface of the Columbia River and into The Dalles. At this point on the trail, our predecessors faced a dilemma—pay a hefty fee and raft down the mighty river past the Cascades or make an equally arduous attempt and pay a toll to surmount the Cascades by way of the Barlow Trail.

We arrived late in The Dalles and dined at Clock Tower Ales, the former Wasco County courthouse. Clock Tower’s burgers are very good and come with the choice of regional beers on thirty-two taps. We camped that night outside the newer Wasco County Circuit Court, where the big love dreams of the Bhagwan Rajneesh and his zealous followers came to an end in charges that ranged from immigration fraud to attempted murder.

The Dalles may be small, but there are options for a place to lay your head after a long day on the trails. Try Celilo Inn, which has some of the best Columbia Gorge views in the region.

In the morning, we walked down to Kainos Coffee, a bright newcomer on 2nd Street. Out front, in two parking spaces, Kainos had created a small covered deck area with tables. Down the street, my favorite Oregon bookstore (and the state’s oldest), Klindt’s Booksellers, wouldn’t open for another hour. Few cars passed by as we drank our coffee, but a horse and buggy did, adding to the ambience of the historic downtown core.

Barlow Trail, Cascade Locks and Oregon City

Zach and I and the dogs decided to forgo floating the Columbia and take our chances on the Barlow Trail instead. First, though, we had to make two quick stops along the Columbia. At Cascade Locks is the Bridge of the Gods, a stunning crossing of the river and the lowest point on the Pacific Crest Trail. Those who have never gotten a visual from Bridge of the Gods should put that on their to-do list. Our second stop was to load a cooler up at Brigham Fish Market, a family-run tribal market and restaurant whose fresh fish brings me back every time I’m in the area.

From Cascade Locks we drove around Mt. Hood into rain and, at higher elevations, sleet pounded the windshield. We pulled off Highway 35 at the Barlow Trail trailhead as snow fell around us. The dogs were in heaven. We were prepared for hell. We improvised our outerwear to prepare for a 5.5-mile, 1,200-foot descent down to Klinger’s Camp and beyond.

As the snow fell and we ran past wooden signs proclaiming Oregon Wagon Route, I thought about the relative hardships I had faced in only a few days out on the Trail—two flat tires, intense heat, dwindling water supply and now June snow and winter temperatures. Any child who came across the Oregon Trail 175 years ago likely faced a lifetime of suffering in those four to six months.

Slowly we climbed the elevation we had lost and, after two hours, had made it back to the Wally Byam-mobile. We quickly hightailed it to Ratskeller in Government Camp for recovery pizza and beer. In the span of three days, we had experienced 90-degree heat and freezing snow. If we hadn’t had access to our Airstream, we would have spent the night at Timberline Lodge—that stalwart atop Mount Hood built by the Works Progress Administration during the Great Depression—or Mt. Hood Oregon Resort down the road in Welches.

Our final leg was a ceremonial stop in Oregon City to cap our updated Oregon Trail road trip. We pulled into town too late to visit the End of the Oregon Trail Museum, but fitting to end at the first territorial capital of the Oregon Territory. Staying on the theme of updating the Oregon Trail, we popped into Coin Toss Brewing, a relative newcomer to the Oregon City scene. The brewery is named for the toss of a coin between Asa Lovejoy of Boston, Massachusetts and Francis Pettygrove of Portland, Maine, that determined naming rights for Portland in 1845. Soon after, the journey of the Oregon Trail would be replaced by train travel.

This road trip, retracing the Oregon Trail at its 175th birthday, brought together many of the best parts in life—an amazing outdoor challenge, the vitality of small towns expressed through brewing and culinary pursuits and a dash of history to ground it all. Though the Trail did give us some hell, we did more than survive on this journey.  175

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