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Ride Chilly Hilly, Wear a Hot Hoodie

4 Feb 2026

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1 min read

Join thousands of hearty winter riders on Feb. 22 on beautiful Bainbridge Island during the 54th Chilly Hilly.
Warm up in our new hoodie featuring a happy harbor seal that will make you blubber with joy.

Paul Tolmé

Begun in 1972, Chilly Hilly is an opportunity to participate in the Seattle area’s oldest and most iconic winter biking tradition.

Held this year for the 54th time on Feb. 22, Chilly Hilly kicks off Cascade Bicycle Club’s major rides season and provides outdoorsy Pacific Northwesterners with a chance to bicycle together in a supportive environment on one of the region’s loveliest bike routes.

It begins with a ferry ride across Puget Sound from Seattle to Bainbridge Island, where more than a thousand people on bicycles disembark the ferry and head out onto the 33-mile course that circumnavigates the island.

Parents on e-bikes often pull their kids on Chilly Hilly

The hills provide a chance to test your winter fitness–although many participants hop off and walk some of the steepest pitches. Because like all Cascade events, Chilly Hilly is a group ride not a race. Everyone who participates wins.

For 2026 we are offering an official 21-mile route that shaves off some of the steeper hills on the southern end of the island.

The short route cuts off the red part of the route — The 33-mile route includes the blue and red segments, while the short route cuts off the red part of the route.

As with all Cascade rides, we supply snacks and hydration at our rest stops so you can refuel and focus on biking. The most highly anticipated rest stop is at the halfway point at Battle Point State Park, where volunteers serve free cookies, snacks, sandwiches and hot drinks.

Once you finish, the party begins. Elated finishers exchange high-fives, pose for silly photos with friends, and warm up with a bowl of hot chili served by the Bainbridge Island Senior Community Center.

Bainbridge Island Rowing transforms its boathouse overlooking Waterfront Park into a hangout zone for family and friends at the finish line, and baked goods and hot drinks are available for sale.

Seal the Deal with a Hoodie

If you’re worried about being chilly at the finish, consider buying our 2026 Chilly Hilly hoodie with the happy harbor seal mascot. Cascade staff members have been testing the hoodies this winter, and everyone is positively blubbering about their warmth and coziness.

Cascade will sell hoodies at the Chilly Hilly finish line expo. Look for the green Cascade tent. If you already ordered a hoodie online when registering, you will receive it at your address–not at the finish line.

Don't let a lack of winter bike apparel stop you from riding Chilly Hilly. Come to the Seattle Bike Swap and E-Bike Demo this Saturday to get deals, steals and bananas bargains on cycling wear and all manner of bicycling gear. We will sell Chilly Hilly hoodies at a discounted price at Bike Swap–another reason to come shop at the Swap.

The Chilly Hilly registration price increases $15 on Feb. 10, and registration closes on Feb. 19, so sign up now and join us on the Pacific Northwest’s most iconic winter bike ride.

As a previous participant raved: “Chilly Hilly is a great way to meet people and make friends while challenging yourself in a beautiful riding location.”

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