Chilly Hilly Bike Ride 2025: Bainbridge Island’s Classic 33‑Mile Winter Ride

Bainbridge Island’s Chilly Hilly Bike Ride is more than a winter workout — it’s a beloved tradition that kicks off cycling season in the Pacific Northwest. Each February, cyclists from across the region and beyond converge on the island for a 33‑mile loop known for its rolling hills, Sound views and camaraderie. Whether you’re pedaling the route or cheering from the sidelines, the ride offers a unique blend of endurance and celebration.

When & Where

The 2025 Chilly Hilly will take place on Sunday, February 23, with the course open from 8 a.m. to 3 p.m. Riders start just steps from the ferry terminal on Winslow Way, after dominating the first four Washington State Ferry runs beginning at 7:55 a.m. The 33‑mile loop circumnavigates Bainbridge Island, offering cyclists rugged climbs and sweeping coastal descents. It’s a chance to see the island from a different perspective — up close, on two wheels.

Why It’s Special

More than 5,000 cyclists tackle the Chilly Hilly each year, earning it a spot among Bicycling Magazine’s top four U.S. rides. Participants climb roughly 2,675 feet over the course, which can feature sunshine, rain or even snow. That unpredictability is part of the charm: you might start the morning under clear skies and finish with snowflakes on your jacket. The ride has been going strong for over 35 years and attracts riders from more than 20 states and British Columbia, ranging in age from toddlers in bike trailers to cyclists in their 70s.

A Full‑Day Experience

The fun starts before the wheels even hit the pavement. The ferry ride to Bainbridge offers sunrise views of Puget Sound and a chance to mingle with fellow cyclists. On the island, volunteers greet riders with free baked goods and hot cider, and the modest entrance fee supports ten local charities. The finish line celebration features a chili feed benefiting the Squeaky Wheels Bicycling Club — perfect for warming up after a day on the road. With a supportive atmosphere and well‑placed rest stops, the Chilly Hilly feels like a rolling block party.

Tips for Riders

- Register early: The event is popular, and spaces fill quickly. Early registration secures your spot and your ferry slot.
- Dress in layers: Bainbridge weather can change quickly. Wear moisture‑wicking base layers, bring a waterproof shell and pack gloves and shoe covers.
- Fuel and hydrate: While there are treat stops along the route, carry water and snacks to keep your energy up on the climbs.
- Check your bike: Have your brakes, tires and gears tuned up before race day. A reliable bike makes the hills more enjoyable.
- Ride courteously: Stay to the right, communicate with other cyclists and yield to local traffic to keep everyone safe.

Not Just for Cyclists

If you’re not riding, there are still plenty of ways to be part of the Chilly Hilly. Residents and visitors line the route with signs and cowbells to encourage participants. Families enjoy the finish‑line festival, where local musicians play and community groups host booths. Volunteers help with everything from course marshaling to serving chili, and the day brings a welcome boost to Bainbridge businesses during the quiet winter season.

Community Impact

The Chilly Hilly isn’t just a test of endurance; it’s a fundraiser that supports local nonprofits and cycling advocacy efforts. Over the years, proceeds have gone toward safe routes to schools, community programs and initiatives that promote biking as a sustainable mode of transportation. The event also showcases Bainbridge Island’s welcoming spirit and scenic beauty, encouraging visitors to return and explore the community year‑round.

Join the Tradition

Whether you’re a seasoned cyclist looking for an early‑season challenge or a newcomer drawn by the camaraderie, the Chilly Hilly is an unforgettable way to experience Bainbridge Island. Mark your calendar for February 23, get your bike and gear ready, and prepare to climb a few hills in the name of fun and charity. If you need tips on where to stay, eat or ride while you’re here, feel free to reach out — I’m always happy to share my local insights.