What to Know About This Year’s Chilly Hilly Bike Ride

chilly hilly 2026Cyclists, check your calendars (and maybe your wool socks), because the Cascade Bicycle Club’s 54th annual Chilly Hilly Bike Ride is rolling out on Feb. 22.

The day will kick off with a ferry ride across the Sound to Bainbridge Island, where a 33-mile loop awaits. The route traces shoreline views of Seattle’s skyline, winds through quiet forested roads, and delivers the kind of rolling hills that live up to the ride’s name.

Chilly Hilly is also a fundraiser supporting Cascade Bicycle Club’s work in advocacy, education, and community rides, making it a feel-good day in more ways than one.

Know Before You Go

Registration closes at midnight on Feb. 19, and there’s no in-person sign-up on ride day. Prices increase by $15 starting Feb. 10, and registering early also gives you the option to have your information packet mailed. If you register closer to the event, packets will be available at your selected start line.

If you choose the Seattle start line, your registration includes ferry fare, and your rider bib doubles as your ferry ticket. Official ferry departures from Colman Dock are at 7:55, 8:55, and 9:35 a.m. You can return to Seattle on any ferry later that day.

chilly hilly 2026On the Route

The main loop is 33 miles, with two short-cut options. New this year is Cascade’s providing of a separate Ride with GPS map for the shortest option. Maps are downloadable (and are best grabbed the day before), printed cue sheets are available, and the route will be marked on the road.

Support throughout the ride is extensive, including Cascade staff, community volunteers, and municipal and county services. There will be SAG vehicles, outriders, traffic officers at key crossings, and even ham radio support the entire way.

Battle Point Park marks mile 15, where riders can refuel with snacks, water, and Tailwind endurance fuel, the event’s official liquid nutrition partner. Expect energy bars, fruit, PB&J sandwiches, and gluten-free and vegan options.

chilly hilly 2026The Finish Line

The reward at mile 33 is sure to warm you back up. You can prepurchase a $10 bowl of chili (veggie or meat) from the Bainbridge Island Senior Community Center and enjoy baked goods and hot drinks at the Bainbridge Island Rowing boathouse. The boathouse will be transformed into a cozy resting spot for riders where friends and family are welcome to join.

Final Tips

Dress in layers, expect rain, bring lights, and make sure your bike is ready for slick winter conditions. All classes of e-bikes are welcome, and riders of all backgrounds are encouraged to participate. Cascade recommends you stash shoes in your day bag — which will be brought to the finish line ahead of you — so you can kick off your cleats for the final celebration.

Take a look at the route ahead of time. If you feel you need some training to prepare, Cascade has an extensive schedule of Free Group Rides in the Puget Sound area.

Chilly? Probably. Hilly? Definitely. But for many riders, this ferry-to-finish classic is the perfect way to launch a new cycling season.