It’s That Time of Year Again to Kickoff the 2025 Biking Year With the 53rd Annual Chilly Hilly on Sunday February 23

By Margaret Millmore 

For many Bainbridge Islanders and Pacific Northwesterners, cycling isn’t just a wonderful way to exercise and enjoy our beautiful PNW scenery, it’s a way of life and an environmentally friendly source of transportation—regardless of the weather or your cycling ability.

Join Cascade.org,  presenter, REI Co-Op and Bainbridge Island for the 53nd Annual Chilly Hilly 33-mile (2,173 feet of climbing) bike ride around scenic Bainbridge Island. The route begins with an early morning ferry ride from Seattle, or you can join directly on Bainbridge Island.

The event takes place on Sunday, February 23, 2025. Start lines at the Seattle Colman Dock Ferry Terminal begin at 7am (ferry times: 7:55am, 8:55am, or 9:35am). Bainbridge Island start line begins at 7:30am at the Bainbridge Island Senior Community Center, located at 370 Brien Dr. SE.

• To register, click here. Note that you must create an account on the website to register.
• E-bikes of all classes are permitted on this ride, as the route is entirely along public roads.

Chilly Hilly is a fundraiser for Cascade Bicycle Club’s programing and advocacy, education, and community rides, such as Major Taylor Project, Let’s Go, Your Streets Your Say, and Pedaling Relief Project. In addition, the registration fees assist Cascade.org in giving back to the communities and organizations that thrive here. To learn more, visit Cascade.org’s statewide advocacy page.

At the 15-mile midpoint, located at Battle Point Park and supported by Rope Skippers, refill stations will be available for your water and electrolyte bottles and light snacks will be provided to power you through the second half of your ride. Fare includes energy bars, chips, nuts, fruit, and peanut butter and jelly sandwiches. Gluten free and vegan snacks and sandwiches will also be available. Bainbridge Island community groups may also provide additional snacks.

At the finish line, you can purchase a bowl of chili (veggie or meat) from the Bainbridge Island Senior Community Center (chili purchases can also be made in advance as an add-on).

Weather And Apparel:

Wear layers and be prepared for inclement weather. Be sure to tune up your bike so that its ready for slick, rainy, and low-visibility conditions. Cascade highly recommends you have front and rear lights, install fenders, service your brakes, and clean your chain.

Pack a bag with fresh, dry clothes so you can hang out after the ride and enjoy the post-event festivities! A bag drop will be available at the Bainbridge Island Ferry Terminal, and all bags will be driven to the finish line outside the Senior Center on Brien Drive.

Support During the Ride:

Per Cascade’s website, this ride is supported by Cascade staff and volunteers, local community group volunteers, and municipal and county services.

Support and gear (SAG) vehicles are present on the route and dispatched when you call the ride support hotline. SAG vehicles can transport you and most models of bikes in the event of a mechanical or minor medical event. You should always call 911 in a life-threatening emergency.

Outriders are volunteers in white, green, and black jerseys that ride on the route, assisting you with minor mechanical and minor medical issues, like cuts and scrapes, dispensing advice and directions, and helping you to Ride S.M.A.R.T.

Medical riders are volunteers on bikes in red and blue jerseys that can assist you with minor medical issues like cuts and scrapes, dehydration, sprained joints, and other non-life-threatening issues.

Mechanics are posted at the Seattle start line, along Northwest Valley Road, and at the mid-point rest stop. They can assist with most common mechanical issues. Full service is available at Bainbridge Island Cycle Shop and Classic Cycle.

Traffic officers are posted at highway crossings.

How It All Began

It was 1972, and a few riders from the Bainbridge Bicycle Club decided it would be fun to challenge our chilly late winter weather with a bike race and tour around Bainbridge Island. The route they outlined ran repeatedly from sea level up to 300 feet and back again, totaling 2,700 feet of elevation change, thus the hilly part. In its humble beginnings, it was called Chilly Hilly 100, because the route was comprised of four 25-mile laps around the island, over the years the route was altered a bit to the 33 miles we have today. It started small with a few dozen riders, and by 1975, when the Cascade Bicycle Club took over organizing the event, it had grown to just seventy-five riders. However, by the 1980s participation was on the rise, and by the 1990s, participation had reached over 5,000 riders, earning the title of “One of Four Classic Rides” by Bicycling Magazine and becoming one of the most famous bike tours in the nation. Riders over the years have endured rain, snow, sleet, and once in a while, sunny and warm weather. They come from far and wide, travelling from more than twenty U.S. States and Canada.

Squeaky Wheels is partnering with Cascade Bicycle Club to provide volunteers for the 2025 Chilly Hilly on Sunday, February 23. Volunteers will direct riders along the route, give much-appreciated encouragement and perform some safety monitoring (e.g. slowing down riders). Shifts are 2.5-3 hours, starting between 8:30 a.m. and 9:30 am or 11 am and 12:30. To sign up click on the provide volunteers link above.  

This story was written in January 2024 by Margaret Millmore, founding editor and publisher of The Island Wanderer. *Images, information and route map provided by Cascade Bicycle Club and The Island Wanderer Blog

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