Chilly Hilly
The honorary kick-off to Seattle's cycling season: a ferry ride to Bainbridge Island then a scenic, hilly 33-mile loop with 5,000+ riders each February.
The vibe
Winter's last hurrah before spring riding
Chilly Hilly is how Seattle cyclists mark the end of winter. Now in its 54th year, the ride starts with a ferry crossing from Colman Dock to Bainbridge Island — which is half the fun, watching 5,000 bikes pack the boat before anyone’s even turned a pedal.
Once you roll off the ferry, it’s a 33-mile loop that hugs the island’s shoreline for skyline views before ducking into forested rural roads and climbing through a string of hills that the name doesn’t undersell. It’s not a fast ride — most people treat it as a social shakeout after months of trainer rides and rain-soaked commutes.
Registration runs cheaper before Feb 10, and the return ferry back to Seattle is free for cyclists. Bundle up: this is a February ride in the Pacific Northwest, and the weather rarely reads the forecast.