Join the Cycle Oregon ‘Challenge’ and ride like it’s 1988

A great excuse to hit the open road and support Cycle Oregon.
(Photo: Jonathan Maus/BikePortland)

In 1988 Guns N’ Roses and George Michael were chart-toppers, puffy sleeve dresses were all the rage, an IBM PC with a whopping 30 MB hard drive would set you back $1,249, and you could buy a new house for a mere $90,000.

1988 Cycle Oregon logo.

It was also the inaugural year for a scrappy little ride called Cycle Oregon that would evolve into an influential nonprofit and one of the best bike events in America.

With Covid claiming their 2020 events and this year’s slate still uncertain, Cycle Oregon has launched a new way to feel some of the magic — and the soreness that often comes with it.

Now you can sign up via Ride With GPS for a challenge to ride the mileage of Cycle Oregon I — 346 miles — before the end of May. All you have to do is sign up on the official challenge website and log your miles with the (absolutely excellent and you should download it immediately if you don’t already have it) Ride With GPS app. If you ride at least 94 miles in the month you’ll be entered into a raffle for a choice of great prizes including free registration in the next week-long, fully supported Classic Ride (a $1,000 value).

Here’s more from Cycle Oregon:

“Grab your fanny packs, neon sportswear, and ten-speeds and definitely don’t forget to feather your hair, we’re riding the very first Cycle Oregon route as our very first Ride With GPS Challenge. Join us for a totally bodacious virtual ride from Salem to Brookings, Oregon as we look back to 1988 and Cycle Oregon I. It’s gonna be hella tubular with some totally radical raffle prizes, too!”

You don’t have to retrace the Salem-to-Brookings route to earn miles (although that would be pretty epic if you did): Challenge participants can earn miles by riding anywhere, even indoors. Once you’re set up, your mileage will appear on a leaderboard where you compete with others to see who rides the most.

So far over 200 people have signed up. Check out RideWithGPS.com for more details. And while you’re there, consider becoming a member of Cycle Oregon’s new Community of Giving (COG) club. The organization wants to reposition their mission to have an even deeper impact on rural communities and they need your help to do it.

— Jonathan Maus: (503) 706-8804, @jonathan_maus on Twitter and This email address is being protected from spambots. You need JavaScript enabled to view it.
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