The rubber first hit the road more than 30 years ago when Cycle Oregon set out on its first organized bike ride. The goal was to bring like-minded cyclists together for a picture-perfect ride, all the while lending economic support to small-town Oregon. Starting with that inaugural trek from Salem to Brookings, Cycle Oregon has built a passionate, loyal community by hosting four fully supported, bucket list-caliber bike rides through Oregon’s most breathtaking landscapes, year after year.

In 2019 Cycle Oregon hosted three, fully supported, bucket list caliber bicycle rides with something for everyone. Classic, an epic week-long journey showcasing some of Oregon’s most spectacular vistas, pristine waters and fine Oregon community hospitality. Joyride, a first class, women-only ride through wine country offering short, medium and long routes. And GRAVEL, a two-day gravel-fest down roads less traveled. This year we are happy to round out our event season with our beloved WEEKENDER event, a two day bike bash featuring great route options for all rider levels, with music, fun and friends in camp each night.

Kickoff Party Details

Wednesday, January 29, 2020

The Loft at 8th Avenue // 2010 SE 8th Ave // Portland, OR 97214

Doors 6 p.m. // Route Announcements 7 p.m.

Our annual Kickoff Party is a free event.


January 29, 2020 // 8 p.m. Pacific // cycleoregon.com

Early bird registration for the 2020 Classic is now open! Sign up before January 29 when registration opens for all events and the registration fee goes up to $1099. CLICK HERE TO REGISTER

Registration for all events, including Classic Rider Guests will be open beginning at 8 p.m. PST on January 29, following the route announcement.

Classic 2020

Early bird registration for the 2020 Classic is now open! Be one of the first riders to reserve your spot on this epic adventure. And if you were lucky enough to join us on our 2019 Classic, you’ll score a FREE 2020 Classic event jersey if you register before January 29! Sign up before January 29 when registration opens for all events and the registration fee goes up to $1099.


The Classic has a ton of new stuff lined up for you in 2020 – like short and long options, gravel options, multiple layover days, bonus activities, and more opportunities to really become part of the communities. CLICK HERE to view a sneak peek of what we have in store for you, and join us at our annual Kickoff Party, when all will be revealed.

2020 Event Dates

GRAVEL – May 15-17

Joyride – June 20

WEEKENDER (It’s baaaaack!) – July 24-26

Classic – September 12-19

Individual event pages on our website may be down periodically in the days prior to the Kickoff Party in order to update our website with the 2020 event information.  All 2020 event information will be available at cycleoregon.com starting at 8:00 p.m. (Pacific) on Wednesday, January 29, 2020.

Ride Archive

Relive rides of yore with our handy ride archive: