: Steens Mountain by Bureau of Land Management

Bite Off a Chunk of Oregon’s Longest Trails

May 12, 2021

Beginning in the Warner Mountains near Lakeview and winding north to the Columbia River Gorge in Hood River, the Oregon Timber Trail is a 670-mile path full of wonder. It takes mountain bikers deep into old-growth and ponderosa forests; past babbling brooks, emerald-green valleys and volcanic terrain; and through quirky, sparsely populated towns along the way. 

“The varied landscapes and communities it travels through are really unique,” says Gabriel Amadeus Tiller, executive director of the Oregon Timber Trail Alliance. “It’s a really educational experience.”

All across the state, there are a handful of special trails that stretch for hundreds of miles, captivating adventurers in Oregon and around the country. There’s Oregon’s 455-mile slice of the famous Pacific Crest Trail, a thru-hiking trail that in its entirety stretches more than 2,000 miles from Canada to Mexico. There’s also the Oregon Desert Trail, a 750-mile, W-shaped path through the arid landscape of Eastern Oregon. For those who prefer an ocean view, the Oregon Coast Trail leads hikers 382 miles along the breathtaking coastline. 

To some, these trails are the ultimate goal, a pie-in-the-sky dream should life ever hand them a few free months. But even if an end-to-end journey isn’t in the cards, you can still do a smaller portion of the state’s most epic trails. 

“It’s really aspirational. It’s something that you have to plan for and work for to really make it a reality,” Tiller says. “Even if you’re doing it as a section, it really feels like you’re part of it.” 

Before you head out the door, read these helpful tips for biting off a chunk of Oregon’s longest trails.

A cyclist pedals across a high-desert plain.
The Oregon Timber Trail weaves 670 miles from Southern Oregon to the Columbia River Gorge — but you can ride a piece of it in a day. (Photo by Leslie Kehmeier)

Terrific Chunks to Bite Off

Ready to start exploring? Consider these ambitious but doable stretches. 

Oregon Timber Trail

Though there are a number of ways to get a taste of this epic trail, the Deschutes Tier is the easiest section of the Oregon Timber Trail. Meandering through the volcanic eastern flank of the Cascade Range, this 113-mile stretch gains 8,000 feet in elevation and is expected to take 3 to 6 days for mountain bikers to complete. If you’re interested in a smaller chunk, there are a number of shorter segments, from 20- to 40-miles, that can be tackled in a day or two days. While the Oregon Timber Trail Alliance gears information to mountain bikers, the trail is open to hikers and horseback riders as well.

Oregon Coast Trail

To get a feel for the Oregon Coast Trail’s breathtaking landscape, try out the section 8, Bandon to Humbug Mountain. Best done with a shuttle, this segment along the Southern Oregon Coast offers hikers a mix of beach walking and small coastal towns. The trail starts at the Coquille River Bridge just north of Bandon, a charming town known for its iconic sea stacks, fresh seafood and coast-inspired public art — so keep your camera handy. Migrating birds will attract your lens at the national wildlife refuge, while the Coquille River Lighthouse is an obvious beacon. Be mindful or else you’ll miss all the coastal glory. Heed signs for campgrounds and water sources, as well as safety information, then look for agates at Floras Lake State Natural Area and admire the rugged coastline around Port Orford to Humbug Mountain State Park.

Oregon Desert Trail

The Steens Loop section of the Oregon Desert Trail is a special segment because it takes hikers to the top of Steens Mountain, a 50-mile long mountain in the Southeast corner of the state. The 25-mile trail is considered difficult, as it gains 4,000 feet in elevation, but the stunning views are well worth the effort. Climbing up through the Big Indian Gorge and down through the Little Blitzen Gorge, two valleys carved by ancient glaciers that offer a peek into the rugged landscape of Oregon’s desert. Snow on the mountaintop lasts until June and July most years, so late summer is the best time to explore. 

Pacific Crest Trail

The 12-mile out-and-back section of the Pacific Crest Trail between Green Springs Summit and Pilot Rock in Southern Oregon takes hikers through the spectacular Cascade-Siskiyou National Monument, a hot spot for biodiversity including more than 200 species of birds. The trail passes by one of the national monument’s top highlights Pilot Rock, a craggy basalt outcrop that is a remnant of a feeder vent from an eroded volcano. Reached by a side trail off of the PCT, Pilot Rock is a worthy detour not only for its views but for its historical significance: It was a beacon for travelers crossing Siskiyou Pass between Oregon and California. 

A rock monolith stands out of landscape.
Access the Pilot Rock section of Pacific Crest Trail outside of Ashland. (Photo by Bob Wick / Bureau of Land Management)

Do Your Research

Each of these 100-plus-mile trails have websites chock-full of pertinent information for those hoping to explore. This includes maps, suggestions for spots to camp, whether fires are allowed and the best time of year to go. 

For example, the Oregon Coast Trail information page, run by Oregon State Parks, alerts hikers to the fact that some of the trail is still under development. About 10% of the route (roughly 40 miles in total) is disconnected, unsafe or inaccessible during certain seasons. 

Covering such a vast distance, these trails tend to vary drastically in difficulty, so it’s a good idea to do some digging into which section best fits your skill level. The Oregon Timber Trail, which is broken into four geographical tiers, has pages dedicated to day rides and multiday loops. The Oregon Desert Trail, too, provides suggestions for shorter trips, and there are a number of resources for finding day hikes on the Pacific Crest Trail.

Sometimes it’s best to learn from those who have done it before, such as taking a page from Connie Soper, who completed the Oregon Coast Trail over the course of three summers’ worth of weekend hikes. Though keep in mind that weekday outings will have fewer crowds.

Hikers descend towards Wildhorse Lake.
The Steens Loop section of the Oregon Desert Trail takes hikers to the top of Steens Mountain and Wildhorse Lake. (Photo by Greg Shine / Bureau of Land Management)

Have a Plan B, C and D

Even after mountain biking for 25 years, Tiller says he still has trouble planning his rides.

“I still probably overestimate how far I can ride 90% of the time,” he says. That’s why he advises against a rigid itinerary that perfectly maps out how far you’ll travel and, if opting for a multiday excursion, where you’ll camp along the way. 

“Have a bunch of options in case things don’t go as quickly or as efficiently as you planned,” he says. “I think it’s good to say, ‘This is our camp goal, but here’s Plan B, Plan C and Plan D.’”

That flexibility, Tiller says, also allows for wondrous surprises. 

“Maybe you find a sweet swimming hole and want to lay around for the day,” he says. “That’s what’s really cool about this. It’s not an organized event, there’s no one way to do it or experience it, so feel comfortable to take it at your own pace.” 

If you’re planning a route that requires a shuttle, then you’ll have less flexibility with your planning. Research which recreation pass you’ll need for the area you’re going, and always carry a printed map or download digital maps as you can’t rely on cell service in remote areas.

If You Go:

Wherever you choose to adventure, check road and weather conditions before leaving. Carry your Ten Essentials, pack out everything you bring in, stay on designated trails and find more tips on how to Take Care Out There. Also, do your part to prevent human-caused wildfires.

About The

Emily Gillespie
Emily Gillespie is a travel writer whose work has appeared in the Washington Post, CNN Travel and Afar magazine. She’s lived in three of Oregon’s seven regions, currently calling Portland home. She and her husband look for every opportunity to hike to a view, bike through wine country and eat their way through a new city.

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