Your Guide to Cycle Oregon’s 2019 Rides

April 25, 2019

Calling all adventure cyclists: Your next great ride is almost here. Cycle Oregon has three epic events planned for 2019, each with its own inspiring route. The Gravel Ride returns with a two-day exploration of the hills of Dufur in the eastern Columbia River Gorge. The female-empowering Joyride takes the scenic backroads of Independence in the Willamette Valley. Then the granddaddy of them all, the Cycle Oregon Classic, invites riders on a weeklong venture around the lava-carved landscapes of Central Oregon, to the legendary Crater Lake and through the Willamette National Forest. And at the end of every soul-fulfilling day are entertainment and incredible amenities at camp.

Tickets are selling fast, so you better start making plans. Find an upcoming ride to join, or better yet, experience them all:

A cyclist pedals on a gravel road with a backdrop of farmland and a snow-capped mountain.
After a popular inaugural Gravel Ride, Cycle Oregon is bringing it to the foothills around Dufur. (Photo credit: Joni Kabana)

Gravel Ride

May 18-19, 2019

Region: Mt. Hood and the Columbia River Gorge

Gravel grinders might tell you the sport offers the best of both worlds: the solace of backroads and the thrills of unpaved terrain. It takes cycling to the next level, with plenty of rewards. So it’s no wonder that after a popular inaugural Gravel Ride, Cycle Oregon is bringing the event back — this time to the foothills around Dufur in the eastern Columbia River Gorge. Known for its agricultural roots, this area features bucolic farms and grasslands with impressive views of Mt. Hood and Mt. Adams around every turn. Incorporated before the turn of the 20th century, Dufur still maintains some of its original relics, including the 1907 Historic Balch Hotel. Learn more about the town’s rich past at the Living History Museum.

The two-day Gravel Grind offers both long and short routes on a blend of gravel and paved roads. High plateaus afford a decent amount of climbing, matched by stellar views. For more details and registration, visit Cycle Oregon.

This year the charming town of Independence sets the scene for Joyride. (Photo credit: Russ Roca)


June 22, 2019

Region: Willamette Valley

For one blissful day in June, female cyclists are invited to ride and unwind on the farming roads of the central Willamette Valley. This year the charming town of Independence sets the scene for Joyride with the Willamette River hugging its borders, surrounded by vineyards, orchards and rolling hills. Take the Buena Vista Ferry — one of Oregon’s oldest continuously operated ferries — across the river at just $1 for a bicycle. Once called the “Hops Capital of the World,” Independence continues its beer-loving legacy with Rogue Ales‘ famed hopyard and tasting room open Thursday through Sunday. For extra credit, ride part of the Willamette Valley Scenic Bikeway, which rolls right through town.

The Joyride offers short (17.8 miles), medium (39.9 miles) and long (63.6 miles) routes. This year there’s an extra twist: the options to also take gravel roads as part of the medium and long routes. For more details and registration, visit Cycle Oregon.

Cycle Oregon Classic

September 7-14, 2019

Regions: Willamette Valley, Central Oregon, Southern Oregon

Adventure awaits on the 31st Cycle Oregon Classic, which this year rolls through some of the state’s most breathtaking scenery. Over the course of a week, riders will chart hundreds of miles along lush forests, scenic rivers, volcanic wonders and America’s deepest lake. Along the way, participants get to explore charming small towns and learn what makes each community so special. Come find yourself in Oregon’s wild places and take that spirit of adventure home with you. Here are some location highlights of the epic 2019 ride:

A rainbow reflects in the cascade of a large waterfall.
Koosah Falls by Sumio Koizumi

Spectacular Rivers

The Classic starts with its sights on two awe-inspiring rivers: Middle Fork of the Willamette River and South Fork of the McKenzie River. The river corridors showcase quintessential Oregon attractions: covered bridges, surging waterfalls and towering trees. If time permits, detour to the McKenzie River Trail, leading to Sahalie and Koosah falls. After clocking 65+ miles, a hot spring soak at Belknap is well deserved.

Sisters to Smith Rock Scenic Bikeway by Russ Roca

Central Cascades

An incredible volcanic landscape reveals itself on day two, when riders take the Old McKenzie Highway to Dee Wright Observatory and beyond. Riders are treated to sublime views of Central Oregon’s iconic Three Sisters mountain range, as well as a gravel option. The Western-themed town of Sisters makes for an exciting lunch stop before riding the peaceful country roads. Camp is set at Tumalo State Park, resting along sounds of the Deschutes River.

Bend Whitewater Park by Jill Rosell

High-Desert Hubs

The route then skirts through Bend, the region’s urban outpost known for an outdoors-minded culture, evidenced in its prized whitewater park. Take the Cascade Lakes Scenic Byway along the Deschutes National Forest boundary towards Mt. Bachelor, amed for world-class skiing in winter and mountain biking in summer. Riders pass Sunriver before cruising into camp in La Pine, the gateway to the Newberry National Volcanic Monument.

Cascade Lakes Scenic Byway by Chaney Swiney

Alpine Lakes

On day four, riders go the distance — 94+ miles — and reap the rewards. (Though the elevation change is less than other segments.) Continuing along the Cascade Lakes Scenic Byway, the route passes ultra-scenic alpine attractions like Wickiup Reservoir, Davis Lake and Crescent Lake. Keep eyes peeled for roaming wildlife. After a significant climb on a straight highway, the cruise downhill to Diamond Lake feels magical, especially knowing a hot shower and entertainment are waiting lakeside.

Crater Lake National Park by Chantal Anderson

America’s Deepest Lake

For centuries, humans have found inspiration in Crater Lake’s brilliant blue waters. As the nation’s deepest lake, the ancient caldera is the centerpiece of its 183,000-acre national park, home to boat tours, seasonal waterfalls and hiking trails. On the Classic route, riders can spend day five biking around Diamond Lake or pedaling 13 miles uphill to Crater Lake. You know what we would recommend: riding the rim of America’s deepest lake. (But if that doesn’t work out, there is another opportunity in September.)

Oakridge by Anthony Smith / Bike Magazine

Stunning Forests

The final days of the Cycle Oregon Classic showcase two Oregon gems: the Umpqua and Willamette national forests. Take the Rogue-Umpqua Scenic Byway along a Wild and Scenic River near several incredible waterfalls (for another day). The famed Row River Trail makes for a pleasant trip to Dorena Lake, the last night’s campsite. When day seven arrives, excitement mounts for the town of Oakridge, a forested wonderland that harbors hundreds of miles of mountain biking trails  — and the closing Cycle Oregon celebration.

About The

Sachie Yorck
Once Travel Oregon's Integrated Marketing Content & Community Manager and forever an Oregon enthusiast, Sachie Yorck loves telling stories that inspire meaningful travel. When in Oregon, she can be found lingering in a waterfall's mist or swirling wine at a vineyard.