Eastern Oregon, a Motorcyclist’s Paradise

June 8, 2017 (Updated June 14, 2017)

I’ll let you in on a secret. Some of the finest riding in the United States remains largely undiscovered — the remote, empty roads winding through the wide-open landscapes of Eastern Oregon.

I’ve clocked thousands of miles on motorcycles. I’ve ridden in every state save for Alaska, and my tastes run the gamut from sport touring to adventure riding to dirt bikes on single-track. But when I first visited Oregon seven years ago, I found the roads so spectacular and varied that I eventually moved here. At first I was drawn to the most popular routes, particularly the twisty roads leading to the Coast and the ever-stunning Highway 101, which weaves for hundreds of miles along the edges of the Pacific. But since then, I’ve learned that some of the best territory for bikers remains hidden east of the Cascade Range.

Recently, I found myself craving the open road — in need of a break from my hectic schedule as a commercial photographer. I’d also reached the bottom inch in my last bottle of bourbon. I figured that was as good a reason as any for a trip on my bike. I blocked a few days in my calendar, called up my buddy Ben and planned four days of leisurely riding from Portland to the crafty enclave of Joseph, home of Stein Distillery, which turns out bourbon to rival the best in the South.

Open Roads Beckon

We leave early on our first day. As we head out, I recall my father’s sage advice: Only travel on two-lane, local roads. The point of riding is to connect with the landscape and the people who live there, so interstates and fast food are off limits. Luckily, Central and Eastern Oregon have so much spectacularly empty and smooth tarmac that you’ll often wonder if you’re the only one on the road. Dad would approve.

We ride from Portland to Detroit Lake State Recreation Area through the town of Estacada. It’s a rewarding route that follows the Clackamas River; the gentle bends of the curves are a nice warmup as we begin the ride. The moist air along the river transitions to the fragrance of fir trees as the road climbs from the river to towering forests before descending to the lake.

Rolling toward Bend, we gain elevation and lose temperature quickly as we climb through the Cascades, forcing us to pull off at one of the many scenic overlooks to don our electric-heated vests. Before I moved here, I always thought of Oregon as a rainy state, but Central Oregon’s high desert, with its clear skies and dry air, realigned my perceptions — reminding me of my home state of Colorado.



One of the reasons I love my KTM 990 adventure bike is that I’m not limited in the kinds of roads I can ride. So outside of Sisters, Ben and I decide to hit the Oregon Backcountry Discovery Route (OBCDR) to mix things up. With over 1,500 miles of dirt double-track crisscrossing the state, it’s a fantastic way to get even farther off the beaten track. Early in the season you can expect mud or snow, but by June the road conditions are more predictable. Nonetheless, you could go days without seeing another vehicle on the OBCDR, so we don’t take this option lightly. We follow Route 4, bypassing the largely straight pavement headed east across the high lava plains in favor of the meandering gravel, dirt and occasionally mud roads.

Come nightfall we camp along a stream near the Painted Hills and peer up at the stars; the lack of light pollution out here makes this one of the best places in the Lower 48 for stargazing. After a cold night in a tent, I like to reward myself with a warm breakfast cooked by someone other than myself, so we take a short ride east on U.S. 26 to the Silver Spur Cafe.

Hundreds of Curves

Heading east from John Day provides us with two spectacular options: Continue on the OBCDR through the Malheur National Forest or hit an amazing collection of corners that virtually no one has heard of, the Dooley Mountain Highway, also known as Oregon Route 245. Having had our fill of dirt, we choose the pavement option.

Dooley Mountain Highway is sometimes referred to as the “Little Dragon” for its ability to stack corners one upon another, not unlike the famous Deals Gap road down South. I’ve ridden North Carolina’s U.S. 128 — “The Tail of The Dragon” as it’s known — a few times, and here’s the thing: Oregon’s version is vastly better because of all that it doesn’t have. There are no shops selling T-shirts, no photographers poised to capture your corner, and no lumbering and lost tourists. Instead there’s space, solitude and all the traction you could want. The tightest section stacks up 188 corners in a short 14 miles as the road climbs from open farmland in the valley below. I’ve ridden this road a half dozen times and have yet to pass more than an old farm truck. It’s glorious.

Having enjoyed a night under the stars and a second day in the saddle, Ben and I treat our selves with rooms at the Geiser Grand Hotel, where the owners always insist I park my bike in the loading zone out front so they can keep an eye on it. With a day of riding behind us, it’s finally time to enjoy a beer at Barley Brown’s Beer down the street, a brewpub serving some great ribs and some of the most award-winning beers in the state.

The next day, we don’t venture out as the Geiser Grand’s morning feast is not to be missed, and the road to Joseph is sparse. Now, there is an easy route to Joseph that’s scenic and smooth, but Ben and I take the back way up the Wallowa Mountain Loop via FS Road 39. Heading east out of Baker City, the roads are gentle, sweeping and bucolic. From here, you can easily take a detour to visit the majestic and almost-secret Hells Canyon. You’ll find that the road conditions on FS 39 vary depending on the winter’s ravages. The road isn’t paved for its entirety, but we’re prepared for gravel, blind corners and the pleasure of riding along several different streams as we wind our way up through the Wallowa-Whitman National Forest.

Ben and I ride into Joseph and stock our panniers with local fare: some grass-fed steaks, farm-fresh green beans and a bottle each of Stein bourbon. Then we head out to our cabin at Trouthaven on Wallowa Lake, where we reflect on our trip from the dock overlooking the crystal water.

We’ve ridden everything from desolate two-track to one of the curviest roads in the entire country, enjoyed great food and craft beers, camped under the stars, slept in an ornate gold rush hotel — and we never once left the state. Indeed, Eastern Oregon is the motorcycle paradise no one knows about.





If you go: Maps can make things look small, but Eastern Oregon is big country. Give yourself a few days at minimum to explore and a week if you plan on picking up the OBCDR for any length. Once you’re east of Bend, services are few and far between, so make it a point to fill your tank anytime you see a service station. It’s not unheard of to go more than 100 miles without finding a gas station.

About The

Gregor Halenda
Gregor Halenda is an internationally acclaimed commercial photographer living in Portland. He was awarded the prestigious Hassleblad Master award in 2008, and his still life clients include names such as Oprah, Neiman Marcus, Prada, Target and Coca-Cola. His passion for motorcycles has led him to race, be a professional stunt rider, and photograph campaigns for BMW, Ducati, KTM, Rev’It! and Scorpion.