: Anthony Lakes

Oregon’s Top Bike Rides

January 2, 2020 (Updated October 19, 2023)

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.

(Cycle Oregon will soon announce its ride lineup for 2024; stay tuned for details.)

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 a costume contest, piping-hot coffee and tasty food stops, a drum line and 5-tier chocolate fountain. Choose your own routes based on what distance you’re up for. 

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 through several beautiful bike-friendly parts of the mid-Willamette Valley, with varying distances available.

The Reach the Beach ride, benefiting the American Lung Association, starts from four different locations: Sauvie Island (100 miles), Vernonia (63 miles), Jewell (30 miles) and OR 202 (14 miles). All riders will then converge for a big finish line celebration in the heart of Astoria, OR. 

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) tests your mettle early in the season, followed by the three-day Cascade Gravel Grinder (Bend) and the five-day, 350-mile Oregon Trail Gravel Grinder (Sisters), both in June.

Pioneer Century ride (Photo by: mthoodterritory.com)



The summer season kicks off with Pedalpalooza (Portland), a month of biking events including the famous 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 several routes. 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 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), Takelma Gravel Grinder (Canyonville) and and West Coast Gravel (Yachats).

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.

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 singletrack trails.

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.

Ride the Rim (Photo by: Sonja Jones)



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 a handful of routes that start in Troutdale. 

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



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.

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