Real Road Trips: Discover Oregon's Outback

A nine-day tour of eastern Oregon
Wild horses in eastern Oregon

I’ve been on board a Palomino named Daisy for so long, I’m afraid to get down, because I won’t be able to get back up again. I haven’t peed in nine hours and I share that information with Kara, the gal riding next to me. She says, “Yeah, I know how you feel,” then energetically urges her red horse into a sea of black cattle that are angry because we’re making them travel for miles in a driving rainstorm.

Kara Wilson’s family owns Wilson Ranches Retreat, a 9,000-acre ranch in central-eastern Oregon, and she is a real cowboy. Nine hours ago, when we started this cattle drive, I thought I was a cowboy, too. Now I am a faker in a sodden cream ski jacket who has to be lowered off her horse, placed in a Dodge “Ram tough” rescue truck and driven back to the ranch house, where I pee, peel off my clothes climb into bed, shiver and whimper.

Why subject myself to this? See those ruts on I-5? I made them. Sometimes you need a different scene: a giant moon to ogle, a rare steak to gobble, a quiet so profound you could hear a star twinkle. For Seattleites, eastern Oregon is a tonic because of what isn’t there: Starbucks, traffic lights, Democrats and fashionable, well, anything.

Travelers: Writer Jenny Cunningham and her man, Kevin Ireland
Purpose: See big land, wild horses; become less “citified”
Days on the road: 9
Total miles: 1,200
Vehicle: Frosty, the sprightly old Audi A4
Navigational aid: Kevin reading a passel of free tourist maps
Most essential road-trip gear: Full tank of gas, food, tent, water, wine
Best detour: Secret spring (shhhh!)
Rookie error: Signing up for an all-day cattle drive
Lesson learned: I am not a cowboy.

Day 1: Today to Moro
We broke this trip into manageable chunks that would ease us into rugged isolation. At four hours from Seattle, tiny Moro makes a great first stop with its newly minted Craftsman Inn (608 Main St.; 541.565.3860; Yes, it’s a B&B in an old house, but it’s not twee, and there’s a wonderful local breakfast. Map by John S. Dykes

Day 2: Technicolor canyons and dog-bears
Frosty the ancient Audi quite enjoyed the first part of this drive, flying through a moonscape of high, dry wheat fields with views of the backside of Cascade giants. About a half-hour down the road, I loved stretching my legs in Cottonwood Canyon (, Oregon’s newest state park, along the John Day River. Kevin liked the bar side of the Round-Up Grill (Condon, 209 S Main St.; 541.384.5100;, featuring fresh local gossip and a crisp chef’s salad. At Service Creek where State Route 19 swirls into the canyon of the Wild and Scenic John Day River, we started seeing weird rock formations in shades of red and turquoise. “Are you sure we are still in Oregon?” Kevin asked. Just when we needed answers, there was the Thomas Condon Paleontology Center. Turns out we had been driving through the John Day Fossil Beds National Monument (about a three-hour drive from Moro;, some of the richest fossil beds in the world. Inside the center, real paleontologists work on fresh finds: fossilized tiny horses with toes and dog-bears that flourished in the post-dinosaur Cenozoic Era.

Day 3: ISO wild horses
Did you know southeast Oregon has bands of wild horses—some the offspring of mustangs brought in by Spanish explorers in the 17th century? The only way to ensure sightings is to take the free tour of the wild horse corral on U.S. Route 20 west of Burns, where wild horses are brought in by the Bureau of Land Management for adoption. But I was hellbent on seeing herds in the wild. That’s how Kevin and I found ourselves piling into a truck with Tracy Westbury, a Bellingham photographer who knows the free-roaming steeds of the Steens Mountain by name. We bumped along the gravel South Steens Road when something came tearing across the range. Pronghorn antelope! But what excited Tracy was a pile of horse poop. “It’s so fresh and moist!” she enthused. She explained that stallions leave stud piles to mark their territory. Many piles and miles later, we were about to give up when I saw a herd of colorful cattle. “Those aren’t cows,” Tracy hooted. “That’s the Hollywood herd!” We hiked over land and under barbed wire, and I got my first good look at a real wild horse. It was the dominant mare, and she looked at me with nostrils flared. We watched about 100 horses until alpenglow bounced off the dry hills and a full moon rose as bachelor stallions tussled. It was a Wild West tableau vivant writ so large I’d have called bullshit on it if I hadn’t seen it with my own eyes. Another iconic vision: the whitewashed Frenchglen Hotel (39184 Interstate 205, Frenchglen; 541.493.2825;, where we spent the next two nights.

Day 4: Highway to the danger zone
I was tired of driving and wanted to sit this day out. But a description of the view from the top of Steens Mountain got me off my butt. “You don’t have words to express what you are seeing,” a fellow traveler said. “You just kind of stand there with your mouth hanging open.” Two hours from Frenchglen, Kevin and I were standing with our mouths hanging open on the edge of the world where Steens Mountain drops a vertical mile into the Alvord Desert—when a thunderous herd of fighter jets buzzed us so close I could see the pilots smiling.
Detour: Secret spring. (Shhh, you must take this to the grave.)
Kevin and I are always on the lookout for under-the-radar hot springs, and that’s why we walked a gated road near the Frenchglen Hotel to a spring we saw on a map called “Barnes.” I figured it was a cold puddle because it sure ain’t famous. Now, the moment of truth: We draped our duds on a bush and shimmied into the perfect circle of clear water. Not hot, not cold. I could have sat here forever in that womb-like place watching minnows swim across my white belly. Then I saw headlights splashing off the cliffs. Cheese it, the fuzz! But wait. I was naked. I’m middle-aged. Was I going to outrun a BLM ranger in my birthday suit? Kevin was cool, nearly dressed, and walked up to the road to face the music. Ranger guy: “You can’t be here after dark. What are you doing?” Kevin: “Leaving.” Back at the hotel, we told the manager what happened and he said, “Spring? What spring?” And that’s what you should say, too. Photo by Kevin Ireland: The author getting ready to soak in Barnes Spring

Day 5: Diamond, population 5

The town sign says it all: Diamond, population 5. Visitors at the convivial Hotel Diamond (10 Main St.; 541.493.1898; way outnumber residents, especially in spring when roughly 200 avian species can be spotted in nearby Malheur National Wildlife Refuge by that other rare bird—Homo sapiens ornithologist. “We’ve been coming to Hotel Diamond since the 1970s,” Theresa Bastian said. “We are birders, but not crazy birders. It’s best here in spring when the birds are in their breeding plumages.” And now a note about food: Both the Diamond and Frenchglen hotels offer dinner at communal tables, which are not to be missed for their homemade bread-and-butter yumminess and delightful conversation. Look out for fresh Hood River apple cake at Frenchglen and strawberry salad at the Diamond. And lest you think there is no shopping out here, prepare to be gobsmacked at the Round Barn Visitor Center (51955 Lava Bed Road; 541.493.2070; The sweeping store’s collections of Vogt sterling silver jewelry, buttery leather saddlebag purses and Olathe boots had me reaching for my Visa card. The unexpected source for this oasis of retail therapy is Dick Jenkins, a rancher whose family homesteaded here in 1880.

Day 6: I am a cowboy

We spent a second night in Diamond to check out the new kid in town, Steens Mountain Guest Ranch (49150 Ham Brown Lane; 541.493.1164; It is an intimate experience, and owners Tim and Susan O’Crowley are Mormon, which worried me at first. But the good company we found here bridged the great political and religious divide. Susan kept the coffee coming as well as swoon-worthy family-style meals, such as smoked tri-tip from their cattle. Tim, a real cowboy, took Kevin and me on a mini-cattle drive that made me smile from ear to ear riding a mustang named Little Britches. When we got back to the ranch, I made a rope with Tim. Maybe I am a cowboy.

Day 7: Get to Wilson Ranches Retreat in Fossil
Pick a road you haven’t driven yet and make a discovery. We went via Highway 78 and found Crystal Crane, a hot spring big enough to swim in and checked out Kam Wah Chung Museum (, a store/clinic/opium parlor frozen in time from the days when the city of John Day had more Chinese than white settlers.

Day 8: Cattle drive
I was so pleased with my performance gathering a few stray cows at Steens Mountain Guest Ranch that I signed up for an all-day ride herding hundreds of cattle at Wilson Ranches Retreat. See intro for embarrassing details. (15809 Butte Creek Road; 541.763.2227; The next morning, the smell of bacon wafting through the floorboards encouraged me to rise from the dead. So here’s the takeaway: The next time I come here (and I will; it’s a lovely spot), I’ll take the two-hour scenic ride, and the next time I eat a steak, I will appreciate the effort it took to get that grass-fed beef onto my plate.

Day 9: Go home
On the long drive home (about five hours), the navigator toggled through photos of wild, open spaces, horses on the run, and a red fire truck rusting in the long, dry grass, and Kevin and I realized eastern Oregon is more than a road trip. It’s a trip back in time.

Want more road trip ideas? Go back to our main story: Five Real Road Trips that will Inspire You to Pack Up the Car and Go