Chilly Hilly

Sunday, Feb. 23, 2020

With chilly February weather and 2,191 feet of climbing, the name says it all!

Kicking off the riding season in the Northwest for its 48th year, Chilly Hilly is a must-do. The 33-mile route around Bainbridge Island starts with a scenic early morning ferry ride across Puget Sound from Seattle, or you can join the crowd directly on Bainbridge Island.

Join us for the ride Bicycling Magazine named "one of four classic rides" in the nation. It's guaranteed to be hilly, probably chilly and always a heck of a lot of fun. So get the dust off your bike and get ready for cycling season early!


  • A scenic cruise on a Washington State Ferry (Seattle start)
  • Free food stop at Battle Point Park
  • Support local Bainbridge charities
  • Finish line festival with a fantastic chili feed benefiting a different Bainbridge Island nonprofit each year (additional cost)

Did you know Chilly Hilly supports our mission to improve lives through bicycling??

Your registration for Chilly Hilly raises funds that allow us to make Washington a better place for people riding bikes. Check out some of our programs like Let's Go, the Major Taylor Project, or our statewide advocacy

Our events are made possible with support from the local communities through which we ride. In addition to supporting Cascade’s programs, your registration fee helps Cascade give back to these communities and the organizations that thrive there. We’re grateful for all their continued support.



Rapha Seattle, a Cascade partner and premium cycling apparel retailer, is extending a 20% discount to all Chilly Hilly Registered riders to gear up for the big day. Stop by the Rapha Seattle Clubhouse at 301 East Pine St. between 4-7 p.m. on Wednesday, February 13 to gear up with their range of cycling jerseys, bibs & rain gear before taking on the hills of Bainbridge Island. 

Register HERE

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