Some come for the landscapes — a chance to experience the ocean, forests, high desert, mountains and all of Oregon’s sheer beauty at a slow pace, on two wheels. Some come for the camaraderie — an opportunity to ride with friends through some of Oregon’s friendliest and most out-of-the-way communities. Some come for the physical and mental challenge of being on a bike for a week, the grand adventure of it all.
It’s all of those reasons that have inspired me to join more than a thousand cyclists in riding the legendary Cycle Oregon Classic ride (September 9-16, 2023) before it ends its 33-year reign. The organization will shift to focus on smaller, shorter rides.
While it will be my first time on this epic 7-day adventure, many riders have returned year after year. There’s no shortage of spectacular organized cycling events in Oregon, but the Classic is the granddaddy of them all. The event is famous for its expertly curated routes with a focus on community. With proceeds from rides donated to the Cycle Oregon Fund at the Oregon Community Foundation since 1996, Cycle Oregon has awarded grants totaling $2.76 million through their community and signature grants. Another $150,000 is set aside each year for community groups that provide services on Cycle Oregon’s events.
Many longtime riders are drawn back to the grind by this stewardship ethos. “I appreciate the work Cycle Oregon does to create as light a footprint as possible on the land while spreading money around small towns with great needs,” says Kendall KIC, a Portland cyclist who’ll ride her 19th weeklong Cycle Oregon event in September 2023. She and other riders of all ages appreciate that it’s not a race, it’s a go-at-your-own-pace ride. “Slow people get to hear and see more,” she says. “Pedaling quiet miles through the woods puts me in a meditative state.”
Cycle Oregon encourages riders to spend their dollars in the local communities they pass through — from purchases of coffee and ice cream to carved Bigfoot statues, Pendleton blankets and other keepsakes (which they can ship home). Each ride ends in a party with food, live entertainment, massage therapists and physical therapists available for appointments. Not to mention the peace of mind of having technical and medical support available on site in case of any issues encountered along the way.
“We’re building community through bikes,” says Cycle Oregon executive director Steve Schulz. “You just come and ride, and we do everything else. And we get to do good and have fun along the way.” Here’s a look at this year’s Classic ride as it takes its final bow.
Wine Country Bliss
The weeklong ride kicks off in the heart of the mid-Willamette Valley in Albany, warming up with a flat and fast roll along parts of the Willamette Valley Scenic Bikeway past farms, orchards, hop fields and acres of wildlife refuge. Take a break in the friendly town of Independence — with Willamette River vibes and a multitude of sweet Main Street restaurants, tasting rooms and shops — before continuing north to Carlton, in the North Willamette Valley. Oregon wine enthusiasts can sip the night away and purchase a few bottles to ship home.
Farm to Ocean Roads
This day’s ride heats up a bit as it heads west from Carlton to the Oregon Coast, tracing the Wild and Scenic Nestucca River under a forest canopy on single-lane roads. Breathe in the scent of the forest as the sunlight streams through the trees, legs pumping on the rolling hills until you reach the Coast Range and the Pacific ocean appears on the horizon. Your destination is Cloverdale, just outside of Pacific City.
Three Capes Scenic Loop
Today riders have two choices. One is to rest and enjoy a well-deserved layover day, perhaps popping into town to support the local businesses. The other is to put in some bonus miles along the Three Capes Scenic Loop, also known as the Tillamook coastline along Oregon’s North Coast. Traveling by two wheels lets you experience the stunning scenery at your own pace, stopping whenever a tide pool, trail, sandy beach or dramatic overlook calls your name.
Coastal Views For Miles
Legs rested, mind free, today is dedicated to picturesque coastline views from Cloverdale to Toledo, just east of Newport. That’s followed by a serious climb east of Highway 101 in the Coast Range, making a sweeping descent into Toledo, on the banks of the Yaquina River.
Arts, Cafes, Seafood and Sunsets
Day 5 is another optional layover day. You can spend your time perusing the specialty shops, art galleries and cafes in the friendly waterfront community of Toledo, or hop on your bike for a short joyride to Newport to do the same there. The Oregon Coast Aquarium, Hatfield Science Marine Center, dining hot spots like Local Ocean Seafoods and more along the Historic Newport Bayfront are a big draw.
Beach to River Vibes
Today you’ll rejoin the Oregon Coast Bike Route along Highway 101 and pedal past landmarks like South Beach, Ona Beach and Seal Rock on your way to the thriving Central Coast town of Waldport. Then you’ll bid farewell to the Coast and head east to the town of Alsea, following the Alsea River as it flows through the Siuslaw National Forest. This stretch of the Alsea Highway is known as one of the most fun and scenic to ride, with gorgeous forested views and plenty of stops along the sparkling river.
A Tranquil Valley Finish
On your final day, treat those legs to a rejuvenating ride along the south fork of the Alsea River. Descend through the forest canopy and thick firs through the communities, fields, farms and vineyards of Philomath and Corvallis on your way to the finish line in Albany. The flat country roads will be a meditation space as you reflect on the journey of the past week and your life journey ahead.