Earning Your Boots in Eastern Oregon

Cows don’t have hangovers, but some have rough mornings. Riding a horse across a valley dotted with junipers doused in a morning drizzle, I see one poking along with two dozen porcupine quills sticking out of its face—leftovers from an overnight tangle with a wrong local.

“That’s going to be a chore, getting all those out,” says a cowboy with a black hat, silver moustache and well-worn chaps stretching below a raincoat. “Quills are barbed, like fish hooks. It’ll hurt her.”

When I moved to Oregon last year, I bought a road map and started marking it up with things that captured my attention. I’ve highlighted the scenic drives I read about in guidebooks or on Travel Oregon’s website and tape on color-coded tags for things I want to see (the Oregon/Oregon State football game) and famous footsteps to follow (the setting of the film Goonies). I call the ongoing project Becoming Oregonian, as I strive to understand a state I don’t really know. Increasingly I find it tilted toward the state’s less talked about east, a wide land of Oregon Trail landmarks, small-town rodeos, rugged high plains, and Pendleton blankets.

Until I started this I hadn’t known Oregon had cowboys.

Phil Wilson is one of seven generations of Wilsons who settled in the hills around Fossil of Eastern Oregon, real-deal cow country just three hours from Portland’s hand-pour coffee lessons. Phil’s ranch B&B, the Wilson Ranches Retreat, fills a meandering valley between grassy hills with views of Mount Hood and Mount Adams. You can ride along too, but be prepared to work. This is not a dude ranch built for sightseers. It’s a ranch for raising cows.

“There’s never a day you can anticipate how the ranch story will unfold—with cattle out, fences down, rains or drought,” Phil says on horseback as we push 40 cattle toward a pen. “That’s the pioneer tradition.”

I’ve ridden here twice before and learn something new every time. This spring, my five-year-old daughter rode a horse for the first time, moving a hundred loud cows into a sunset up a mountain. Despite a near fall, she said the next morning, “I want to stay here forever” (she shares the experience on this episode of the 76-Second Travel Show).

The Wilsons’ B&B living room has leather sofas, cowboy hats hanging on a pillar, coffee table books on local rodeo, and a TV set that never seems to get turned on. It’s built for instant community: a minglefest of offsite workgroups, Pacific Northwest weekenders, and Europeans tracking down American ancestors. Even an Amish group recently spent a week. (“They’d talk to horses and sing these songs that’d bring tears to your eyes,” Phil’s wife Nancy says. “I sobbed when they left.”)

This time, ten of us fill the home, including a young British couple who admits to coming because of buying $300 Lucchese cowboy boots after watching City Slickers. “We had to find a ranch.” After a seven-hour ride, herding cattle over the mountains, Phil’s daughter Kara tells them, “You earned your boots today.”

After dinner Dan Robinson—a local singer and artist transplant—drops by to test out songs for his band’s upcoming show in Fossil. Over his shoulder, an American flag flaps outside the window as he plucks his guitar and sings versions of Townes Van Zandt and Johnny Cash songs.

“One of the reasons I think I’ll stay here is because there’s no thrum,” he explains from below his felt black hat. Thrum? “Background noise. I never realized how much constant noise there is in a place like Portland.”

I’m spending a couple of days to ply east, pausing plenty while going on/off the 290-mile Journey Through Time scenic byway, marked by the state with roadside signs. The scenery alone leads you as it leads past rushing streams and walls of ancient rock and into the rugged red and blue landscapes of the John Day Fossil Beds National Monument.

I pass through the Picture Gorge, where cracked layers of mountain jut sideways from the banks of the rushing river, and ride an hour more east into the town of John Day for a late lunch of chili and IPA beer at 1188, a new microbrewery. It’s woodsy yet industrial, with corrugated-tin wainscoting and stocky wood stools painted silver. The busy bartender who delivers food and pours pints tells me 1188’s been a popular addition to the “burger-and-fry, Keystone Light places” you find around town. “But I sure hope we can get a waitress soon.”

It’s good, but I’m in town to visit a humble, built-out building of stone and wood planks that’s home to a Wild West I didn’t really know existed.

The Kam Wah Chung & Co was a gathering place for the Chinese community from the 1880s, after Canyon City, a few miles south, boomed in a brief Oregon gold rush. Plain wood floors creak as you step into the dark interiors, splitting into tightly packed cubbies with different purposes: a storefront, a bunking area in the kitchen, a corner apothecary with bottled rattlesnakes and herbs stored in old cigar boxes. A recording with Chinese actors and sound effects plays as you get through. Everything’s original, from the 1920s calendars to the dehydrated orange left at an altar in 1948, when it closed its doors to business.

Afterward I visit a small hillside cemetery to pay respect to the two Chinese immigrants who put this together, Dr. Ing Hay (or “Doc Hay”) and businessman Lung On. There I find a gray-haired woman in a man’s tweed jacket eyeing a few tombstones. Susan’s there to visit some old classmates and happily leads me to their graves. “My mother used to go to Doc Hay,” she says.

Racism and violence plagued many of the early years of the Chinese community here, but Doc Hay helped change that. He was a rarity—a trained doctor, even if a herbologist and pulsologist—and his positive results for flus and loose bowels turned many locals into fans of his smelly potions.

“My mother wouldn’t see anyone else.”

A few miles south of John Day is Canyon City, home of the gold rush. The museum’s closed for the season so I peek at the main street murals on old buildings, then stop into Russell’s Custom Meats & Deli, a popular family-run place specializing in various meats and offering services like “mobile slaughter.” A giant buck trophy looms over a side table, where I sit a bit with co-owner Kathy Moss, who also stocks a collection of her poems.

“It’s something I have to do,” she says, always smiling. “I seldom write poems about myself, but on the colorful people I meet out here.” She starts to recite one she wrote for an 89-year-old cowgirl poet she knows, when a customer comes in.

“What do ya need?” she asks cheerfully.


“I’ll see if I can get you some,” she says, getting up. “How much do you need?”

“Oh, 30 dollars.”

Kathy bags a few fistfuls of stringy sticks of fresh beef jerky into a brown bag, then returns to finish her poem.

The setting of Prairie City, a 20-minute ride east, looks like an image of Montana: a wide prairie valley rimmed with the snow-dusted Strawberry Mountain range and topped by big skies. In town, I see handmade “taxidermy” signs and bike lanes leading into a nicely kept-up downtown with brick buildings turned into cafés, diners, bars, and the recently renovated, century-old Historic Hotel Prairie, where I’m staying.

In the morning I breakfast a couple of doors down at Chuck’s Little Diner, sitting by a retired cowboy in a jeans jacket at the counter. Chuck’s watching the Today Show, then joins a couple who comes in after me. He starts into a soliloquy about ghosts he reckons lives on Civil War sites.

The owner’s cheerful wife, Valeria, refills my coffee and then walks me over to a wall full of century-old photos, including shots of Bates, her childhood home, a mining town that vanished after the mines closed. Afterward she lived in Baker City, an interstate town, then “got pregnant, married, and moved here.” Not sure if it was in that order, and I don’t ask. So I bring up fungus.

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Just east of town, the Malheur National Forest, is home to the world’s biggest fungus. At 642 acres in girth, it’s called the “humongous fungus” and is deemed to be the world’s biggest organism. But you won’t find fungus T-shirts in town. In fact, only a few locals I ask had even heard of the great subterranean thing lurking in the hills. Valeria shakes her head. “I learn more about this area working here than I ever did growing up.”

After breakfast, I drive west, over the Dixie Pass, and detour onto forest dirt road into the woods, heading about ten miles in to find the heart of the fungus. Rocks pop up on the belly of my econo rental, as I bounce slowly along the twisting, rising road. About halfway to my target, the road turns to craters of muddy roads and bigger boulders. It’s too much for my Hyundai.

I stop the car and get out to ponder my failure in the brush a bit. Views lead over the tops of trees toward a distant Blue Mountain range. I start looking for odd mushrooms, but find myself focusing instead on fallen golden needles of western larch that pad the path. Many locals mistakenly call these tamarack trees (they grow only farther north and to the east). I crouch with a few tiny ones that look like gold Christmas trees to pose for a pitiful selfie.

Despite the claim of my map, I really don’t know if trying to find a fungus qualifies me as more “Oregonian” or not. Or if listening to cowgirl poets or taking quiet two-laner trips between cattle ranches and volcanic landscapes does either.

But it feels like a step in the right direction.


This ride into eastern Oregon looks like a few hours on a map, but you’ll be happy with three or four days, minimum. With shorter time, you could see Fossil and Painted Hills, then cut back toward Bend via the Smith Rock State Park, a climbers’ haven.

Find a place to hang your hat: You need to plan if you’re not camping. The best places to stay along the Journey Through Time drive are the Hotel Condon, just north of Fossil; the Wilson Ranches Retreat, which includes a wonderful family-style, chatty breakfast; Mitchell’s Painted Hills Vacation Rental, a two-cottage property on a hill above town; and in Prairie City, Historic Hotel Prairie and the Riverside School House B&B, set on a ranch outside town.

Bring your boots: Even if you’re not riding a horse, hikes abound. Outside Prairie City, the Strawberry Mountains have a few longer hikes; I took one to Strawberry Lake and spied on hundreds of trout splashing in a meandering stream on the far side. William Sullivan’s Eastern Oregon is the definitive hiking guide for the region.

See some sites: The John Day Fossil Beds National Monument squeaks onto Oregon’s self-appointed Seven Wonders list, and it’s particularly worth going to the Painted Hills and Sheep Rock, with blue formations and a paleontology center to see. John Day’s Kam Wah Chung State Historical Site justifies a detour.

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