Oregon’s Best Bike Events for Riders of All Levels

Whether you’re a serious racer, a gravel rider, mountain biker, or just like to ride for the scenery, Oregon has a bicycle event for you. The League of American Bicyclists listed Oregon as the second most bike friendly state in the country. It’s also the only state to have established a scenic bikeways program for riders who want to explore the state by bicycle.

Whether you’re looking to set a goal like a century ride or doing a large race or just want to get out on your bike with a group of people, there are events for all styles of riding.

Oregon races and rides for those looking for a challenge

Race Across Oregon does an annual 500-mile race in a loop that begins in The Dalles and goes through the high desert region of Oregon with more than 37,000 feet of elevation. The route showcases some of Oregon’s best scenery, a nice perk for what might be the hardest race in Oregon. For good reason: It’s one of the oldest qualifying events for the ultra-distance road cycling event, Race Across America, which began in 1982 and is one of the longest endurance events in the world.

Mudslinger events are well known to riders in Oregon and beyond. For serious riders who want to make the most out of the Pacific Northwest’s dry season, gravel/road riders can sign up for the Oregon Triple Crown which sets them up to ride three out of six fully-supported and timed rides in the state.

Oregon’s best rides and races cyclists who don’t want to worry about logistics

If you don’t want to limit yourself to Oregon, it’s worth considering the Seattle to Portland Bicycle Classic. This 206-mile double century ride goes through urban and rural areas and can be done in one or two days. Hotels and food stops are clearly marked along the route and the organizers can help with bus passes or bike transport. This ride has been going since 1979 and the kinks have been worked out so that participants only need to focus on pedaling.

Nonprofit group Cycle Oregon does a number of great events throughout the state but signing up for their Rally ride is a perfect way to see the state. There are different route options which range from 198-298 miles. Recently Cycle Oregon started allowing e-bike riders at their events which further open these longer rides up to cyclists of different endurance abilities.

All-ages friendly cycling events in Oregon

Mountain bikers should prepare now if they want to sign up for the Sisters Stampede, the largest cross country mountain bike race in the Pacific Northwest. The race only allows a maximum of 500 riders for this event in Sisters, Oregon. Your fellow riders for this short mountain bike race can be anywhere from seven years old and up.

For a few days every year, Oregon’s only national park kicks cars out and lets cyclists and pedestrians have all the fun. The annual Ride the Rim event at Crater Lake National Forest opens up two car-free days that are the perfect time to ride your way around the state’s most famous lake.

Right as Portlanders are ready to crack from the rainy weather, the annual Worst Day of the Year Ride is there to get people out on their bikes. The event started in 2000 and has taken place almost every year since at the wettest and coldest time of the year. There are multiple routes, a costume contest, and lots of stations offering hot beverages to cold riders.

Oregon bike events for riders looking to have a little fun

Every year, Portland, Oregon hosts an event for the World Naked Bike Ride where riders gather to ride in their birthday suits on secret routes through the city.  It’s not surprising that the “keep it weird” city hosts unorthodox bike events.

In spring, the Ladds 500 encourages bike riders (and those with other types of manual-powered wheels) to circle a neighborhood roundabout until they’ve cycled 100 miles. Since the first event in 2016 when 40 people took part, the event has exploded in popularity. In 2024, an estimated 500 people took part.

There are many Pedalpalooza events that celebrate all things bicycle in Portland, Oregon but none are more unique than Bike Play an annual event that combines a live theater performance and a bike ride. This is one you have to see in person.

How to stay safe on a group bike ride

A growing number of people taking part in group rides like the Ladds 500 or Bend’s 4th of July Freedom Ride have brought up concerns about the events getting too popular or riders becoming unruly. On some rides, additional riders make the risk of serious injury lower since speeds are reduced. But cyclists should remember to bike responsibly while having a good time.

Many people enjoy bike pub crawls that involve stopping for food or a drink at local restaurants or bars. Riders should make sure to stay hydrated and not drink to the point where they become impaired or over the legal limit. Staying vigilant of cars, pedestrians, and other obstacles while riding is the best way to avoid getting into a bicycle crash.

Since bicycles are considered vehicles under Oregon law, cyclists have to follow the same rules as drivers when it comes to obeying traffic signs and signals as well as not being under the influence of alcohol or other substances while cycling.

Low light conditions increase the likelihood of getting into an accident. This means that long rides or riding at night mean cyclists should take extra precautions. (Click here for more information on the most likely time to get into a bike accident.) When riding at night, wear visible clothing and have appropriate lights and reflectors on your bicycle. Driving an automobile while fatigued is well known to be a risk factor for accidents on par with being under the influence. Cycling when overtired can also make riders less aware of their surroundings and more likely to get into an accident.

If you are in an accident while riding or racing in Oregon, call an experienced bicycle accident lawyer. As a fellow cyclist, Matt Scarborough will support you in getting the resources you need to recover from a crash.

Bicycle Accident Team Members in Drake Park. From left: Stacy Simmons, Matt Scarborough, and Amy McConnell