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 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
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Jonathan Maus (Publisher/Editor)

Jonathan Maus (Publisher/Editor)

Founder of BikePortland (in 2005). Father of three. North Portlander. Basketball lover. Car owner and driver. If you have questions or feedback about this site or my work, feel free to contact me at @jonathan_maus on Twitter, via email at, or phone/text at 503-706-8804. Also, if you read and appreciate this site, please become a supporter.

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3 years ago

I bought a house in Salem ( near the start of the original ride) in 1987 for only $45,000 and a brand new Bridgestone MB1 that same year for $235.00. Good Times.

Middle of the Road Guy
Middle of the Road Guy
3 years ago

RidewGPS is such a fantastic app. It is incredibly relied-upon in the gravel community.