: Anthony Lakes

Oregon’s Top Bike Rides

January 2, 2020 (Updated December 9, 2022)

Whether you’re a recreational biker, a mountain bike shredder or a hardcore cyclist, Oregon’s streets, trails and gravel grinds await! Oregon’s cycle advocates are so committed to two wheels that the state was the first to develop dedicated scenic bikeways. With hundreds of organized events every year, it’s easy to gear up for the perfect ride for your interest and ability in all corners of the state.

Gorge Gravel Grinder (Photo by: Breakaway Promotions)



While it may be windy and rainy, the Worst Day of the Year Ride (Portland) makes up for the inclement weather with costumes, tasty food stops and even a five-tier chocolate fountain! Choose either the 15-mile urban or 42-mile challenge course.

The Pedals ’n Pears (Medford) bike rides offer four distances from the easy and flat Comice Family Ride along Bear Creek Greenway to the challenging Royal Riviera Metric Century through the blossoming pear orchards of South Medford. 

The Monster Cookie Metric Century Bicycle Ride (Salem) starts at the State Capitol and loops 62 miles through Champoeg State Park. Participants also have the option of biking half the route.

The Reach the Beach ride, benefiting the American Lung Association, starts from four different locations: Portland (101 miles), Carlton (72 miles), Amity (55 miles) and Grand Ronde (26 miles). All 3,000 riders then converge on Cape Kiwanda in Pacific City. 

For gravel grinders, the Cycle Oregon Gravel ride takes tires to the roads less traveled with multiple route options over two days in May. 

Also at the beach, the Cannon Beach Fat Bike Festival pumps a whole weekend with fun including beach rides, scavenger hunts, games and bonfires.

Part of a three-race series, the one-day Gorge Gravel Grinder (The Dalles) and three-day Cascade Gravel Grinder (Bend) both take place in the spring, followed by the five-day, 350-mile Oregon Trail Gravel Grinder (Sisters) in June.

Looking to get away with just the girls? Click here to read about some all-women rides through the scenic, wide-open spaces of Eastern Oregon.

Pioneer Century ride (Photo by: mthoodterritory.com)



The summer season kicks off with Pedalpalooza (Portland), a month of biking events including the wildly popular World Naked Bike Ride with about 10,000 riders. It’s considered the largest ride of its kind in the world. Pedalpalooza also includes rides in neighborhoods closed to vehicular traffic as part of Sunday Parkways.

Riders get to pedal along one of Oregon’s iconic roads, the Historic Columbia River Highway, as part of the Gorge Pedal Experience (Cascade Locks), which features both an 11-mile family ride and the 46-mile climb ride. Another beautiful route, Tour de Fronds (Powers) invites cyclists to choose one of six routes through Southern Oregon’s Coast Range.

The Pioneer Metric Century includes several beautiful routes of varying lengths around the Champoeg, Canby, and Molalla areas. 

The Providence Bridge Pedal (Portland) is a signature summer event, drawing nearly 20,000 people with the promise of biking Portland’s seven bridges, all free of cars.

The Oregon Gran Fondo (Cottage Grove) isn’t just a race but a community event where everyday cyclists can start with the pros on the first stage of the course, similar to the cycling traditions of Italy and France. It’s part of Oregon’s Triple Crown races, which also include the Sasquatch Duro (Oakridge), Oregon Coast Gravel Epic (Waldport) and Takelma Gravel Grinder (Canyonville).

The four-stage Baker City Cycling Classic is one of the premier cycling events in the Pacific Northwest, ending at Anthony Lakes Ski Resort. Later in the summer, Anthony Lakes hosts a one-day Mountain Bike Festival.

Cycle Oregon’s weeklong Classic ride has inspired bicycle sabbaticals for more than three decades. Cycle Oregon also hosts the one-day, women-only Joyride in June and the fan-favorite Weekender in July, both with multiple route options available.

Another big draw for intermediate and advanced mountain bikers is the three-day Mountain Bike Oregon festival (Oakridge) with hundreds of miles of world-class single-track trails.

Ride the Rim (Photo by: Sonja Jones)



One of the hallmarks of fall is Cycle Oregon’s Classic ride, which changes routes each year but is always epic — a weeklong journey that showcases some of Oregon’s most spectacular vistas, pristine waters and community hospitality. Experience similar fun and hospitality on the two-day Gravel ride (held in spring) and the women’s daylong Joyride (summer).

The Vineyard Tour ride (Roseburg) combines two of Oregon’s favorite things: cycling and wine! This event’s routes range from 15 to 100 miles on the rural roads of the Umpqua Valley wine country. Of course, both wine and craft beer await finishers. Harvest Century is another event with five possible routes that wind past Willamette Valley wineries with glimpses of Mt. Hood. 

Experience one of Oregon’s natural wonders from the saddle of your bike as part of Ride the Rim at Crater Lake National Park. The first 25 miles is car-free. If you choose to complete the entire loop, the remaining 8 miles will be on a shared road with no shoulder and significant inclines.

But know this: You don’t have to wait for an organized ride to enjoy Oregon’s splendor. There are 17 scenic bikeways across the state, ranging in distance from 29 to 174 miles and across all abilities. It couldn’t be easier to hit the road with curated routes, detailed maps and clear signage. To pick your first epic ride, click here.

Winter Wonderland



In January Cycle Oregon announces its ride routes for the coming year. The group plans bucket-list rides that showcase spectacular scenery while supporting small towns along the way.

During the holidays, bring the entire family to Portland International Raceway to bike the lights at Winter Wonderland, the largest holiday light show in the Pacific Northwest.

About The

Shellie Bailey-Shah
Shellie Bailey-Shah is travel writer who has the distinction of having visited all seven continents, but she favors her home state of Oregon. She lives with her husband and sons in Portland and has logged thousands of miles behind the wheel of the family's RV.

Trip Ideas

  • My Journey to Long-Distance Cycling

    When I moved to Portland after college, I noticed a colleague of mine consistently biked to work. He would walk by my desk styled head to toe in Gore-Tex, a bike bag and helmet in...
    Kate Sappell , Guest Author
  • Ride the Oregon Scenic Bikeways

    These aren't your typical bike routes. Oregon Scenic Bikeways are the state's best road rides, showcasing incredible, only-in-Oregon scenery — along high-desert highways, past geologic wonders, on covered bridges, next to roaring rivers, over snowy...
  • All Bodies on Bikes in Oregon

    Watching along on social media as other people in larger bodies went on Oregon hiking adventures, I became inspired to start speaking about my own experiences as a fat bike rider. This past spring I...