Cycle Oregon Showcases State with 2026 Tours
The 5-Day Rally, plus Gravel and Joyride weekends, continue group’s bicycling tradition.
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The Classic is gone, but Cycle Oregon rolls on.
The non-profit group, which has been leading bike tours since 1988, was famous for its seven-day Classic event. A staple in each summer’s cycling calendar, the point-to-point-to-point experience attracted as many as 2,500 people as it explored most corners of the state.
But the Classic faced its share of bad luck several years back. Wildfires and smoke occasionally prompted route changes and, in 2017, forced the entire event to be canceled.
Then there was COVID, which sent the Classic into a two-year hiatus. Finally, after 33 years, it disappeared with the conclusion of its 2023 tour.
But as the Classic faded away, Cycle Oregon shifted to a five-day “Rally” event, a ride similar in many ways to its predecessor.
“The transition from the Classic to the Rally was driven by many factors from operational demands to what riders wanted to do,” Chris DiStefano, Cycle Oregon’s communications manager, tells me. “Classic was a much longer experience for participants, up to nine days with travel time to and from the event included.
“In current times, most folks just don’t do the weeklong-plus getaways any longer,” Chris continues. “At five days, Rally still feels like an epic adventure but one that can be fit into a contemporary lifestyle.”
In fact, Cycle Oregon continues to tinker with its event lineup. There once was The Weekender, a family-oriented two-day event in the Willamette Valley. That’s gone in favor of a pair of events — Gravel and Joyride. Arrive on Friday, then pedal Saturday and Sunday.
Here’s a quick rundown of all three 2026 events by dates. Complete details are available on the Cycle Oregon website.
Gravel
May 8-10
Tygh Valley
Cycle Oregon has this long-standing affection for the Tygh Valley in north-Central Oregon and has returned with different events many times. I rode there during the Classic in 2014 and while following the Sherar’s Falls Scenic Bikeway nearby a decade later. I can testify to its simple beauty and open ranch lands with views of Mount Hood by day and starry skies at night.
“Oh, yeah, we love Tygh Valley, and we’ll keep coming back here for so many reasons,” Chris says. “One, it’s a world away without being far away which makes it ideal for a weekend escape. We also return because the Wasco County Fairgrounds serves as an incredible natural amphitheater for the event.”
Where is Tygh Valley? Follow Highway 197 for 30 miles south from The Dalles. You can’t miss it.
There are two route options each day. Saturday features a 35-mile loop with 2,830 feet of elevation gain and a 65-miler with 5,200 feet of climbing. Both are roughly half gravel and half pavement.
Sunday’s rides are 34 and 53 miles with similar elevation gains. Expect even more paved roads this time.
“It’s mixed-terrain, meaning riders should be comfortable on unpaved surfaces,” Chris says. “It requires a sturdy bike and a bit of experience off road. Last year’s Gravel was 99 percent off road, but Tygh Valley is much more of a mixed-surface gravel vibe with nice, paved sections linking routes. This is an ideal event for someone who is curious about gravel and has some fitness on the bike.”
Chris’s gives Gravel his personal degree-of-difficulty assessment: 6/10
Joyride
June 12-14
Pleasant Hill
Cycle Oregon is going to Pleasant Hill, just southeast of Eugene, for the first time.
Women, female-identifying, and nonbinary riders can take this weekend spin around Lane County. Saturday features four routes, one being gravel, ranging from 24 to 70 miles. There are three routes on Sunday, two on pavement (22 and 60 miles) and one on gravel (42 miles). Watch for covered bridges, farm roads, and the ever-present Willamette River.
“(This is) the perfect backdrop for Joyride’s spirit of rejuvenation,” Chris says. “It’s an area that feels tucked away from the world but is still close by for an easy weekend getaway.”
He says the weekend is about discovery for riders of all types and abilities.
“Some riders choose the challenge of a long day with lots of climbing while some just want to get a couple hours in the saddle and then enjoy the community,” Chris says. “We will offer a number of riding clinics at Joyride, including gravel how-to’s led by experienced coaches.”
Chris’s rating: 6/10
Rally
August 28-September 2
Grants Pass and Jacksonville
Anyone who’s ever explored Southern Oregon knows this is one of the region’s best-kept cycling secrets. Rally explores sections of the Rogue River, the Rogue Valley, and the Applegate Valley over five days. One route also samples the Cascade Siskiyou Scenic Bikeway.
Instead of traveling from city to city as the Classic did, the event camp stays in Grants Pass for two nights before relocating to Jacksonville for the final two nights. Everyone pedals back to Grants Pass for one last ride.
There are paved and gravel route options each day, though the actual gravel surfaces never total more than 36 percent of that day’s ride.
“Five consecutive days is a lot of time on the bike so anyone choosing to ride Rally should have a proper summer of training in them before rolling into camp,” Chris says. Following the shortest routes each day will accumulate nearly 190 miles and 9,000 feet of elevation gain in five days’ time. Taking the long way will earn 300 miles with almost 17,000 feet.
“We’ve got full on-course support with well-stocked rest stops, SAG vehicles, and great in-camp meals,” he says. “Oh, and there’s daily yoga and massage available.”
The difficulty score: 7/10
Who Benefits?
A Cycle Oregon trademark over the years has been its commitment to supporting rural communities. Local organizations always help support the riders whenever an event comes to town, and the organization donates money back as a thank you.
That tradition lives on through the Cycle Oregon Foundation, which Chris calls “vehicle” for some incredible statewide initiatives:
Jump Start is the flagship bicycle education program, with a focus on rural communities. “Under the Safe Routes to School umbrella, we provide schools with a full fleet of bicycles, helmets, and a specialized curriculum.”
Working with elementary school physical education teachers, the program introduced bike safety and fundamentals to more than 7,500 students in 60-plus Oregon schools. “Of those 7,500 kids, around 24 percent learned to ride a bike for the very first time,” Chris says.
A personal note: I saw this firsthand as a volunteer in Salem schools. Helping a child learn to ride is good, but the reward is seeing their excited smiles once they succeed.
There are two more programs.
Summer Kids Camp: “We are expanding our Kids Camps in 2026 to Portland, Hillsboro, and Bend. These week-long camps are designed for ages 8-12 to build ‘confident commuters,’” Chris says. “It’s about teaching the next generation that a bike is more than a toy; it’s independence.”
Grants: The Cycle Oregon Fund has awarded 387 community grants totaling $3.25 million since 1996. “We’ve funded everything from historic building preservation and trail infrastructure to pump tracks and skills parks in towns,” he says.
Dan Shryock is a travel writer and career journalist who focuses on cycle tourism. Based in Oregon, his work has appeared in magazines and websites in California and the Pacific Northwest. His book, “Cycling Across Oregon: Stories, Surprises & Revelations Along the State’s Scenic Bikeways” is available on Amazon.