2027 Cycling Events
All you have to do is pedal
We’ve got you taken care of – When you sign up for a Cycle Oregon event, you are stepping into a fully supported cycling community where every detail is taken care of from start to finish. We handle the logistics with multiple daily route options, our renowned rest stops and volunteers, full course & in-camp mechanical support, and delicious catered meals so you can focus entirely on the open road. At the end of the day, a vibrant camp life awaits with hot showers, cold drinks, daily yoga, and live music to celebrate the miles. It’s everything you need to explore Oregon from the saddle at your pace and on your timeline.
Early Bird Registration Opens November 17th, 2026
Cycle Oregon Rally
Wallowa Wonder
August 27 – September 1, 2027
Rally is the signature Cycle Oregon multi-day cycling experience, riding deep into the breathtaking landscapes of the Wallowas for 2027. This is a week of riding through welcoming Oregon communities, enjoying fully supported camp life, and forming deep connections with fellow riders and local residents. Multiple routes daily with road or gravel options split between our two basecamps in Elgin, Oregon and Enterprise, Oregon.
Early Bird Registration Opens November 17th, 2026
Cycle Oregon GRAVEL
Madras, Oregon
May 14 – 16, 2027
GRAVEL is our weekend celebration of unpaved exploration and backcountry camaraderie. This event pairs challenging mixed-terrain riding with a relaxed, fully supported camp life that connects riders with a new Oregon community each year. Multiple daily route options offer varied terrain and scenic vistas, backed by full course support, live entertainment, and local hospitality. Remote roads and shared adventure—this is Cycle Oregon off the beaten path.
Early Bird Registration Opens November 17th, 2026
Cycle Oregon Joyride
Pleasant Hill, Oregon
June 25 – 27, 2027
A women-centric weekend of bikes, natural splendor and belonging. Multiple daily routes with road or gravel options, in-camp clinics, live entertainment and the famous Saturday night Sparkle Prom. Every body; every bike – every Joyride.
Cycle Oregon Joyride is exclusively for women, women-identifying and non-binary riders.
Early Bird Registration Opens November 17th, 2026
