AdventuresNW
It’s best to enter winter with a plan, lest the wet weather dampen your enthusiasm for biking. My winter plan is to set a goal, to be prepared, and to be opportunistic.
My perennial goal is to ride the annual Chilly Hilly on Bainbridge Island. First held in 1972, the Chilly Hilly is an aptly named 33-mile circumnavigation of Bainbridge that starts and ends with a festival in Winslow.
Organized by Cascade Bicycle Club, Chilly Hilly is the annual kickoff to Washington’s bicycling season. Mark your calendars for Feb. 23, 2025, and join the thousands of people who have completed this historic bucket-list excursion.
Riding Chilly is doubly good because it provides inspiration to train, and proceeds benefit Cascade Bicycle Club’s advocacy, education, and community-building programs. But riding in winter requires more than motivation; it also requires preparation.
Preparation means having the right waterproof gear and bike setup for foul conditions. For me, comfortable winter cycling is about two things: fingers and toes. Keep your hands and feet warm and dry, and you can bike through the coldest and soggiest of Pacific Northwest winters.
In addition to a rain jacket and rain pants, here are a few items from my gear stash that keep me pedaling when the weather turns cold, damp, and dark.
- Waterproof Socks. I recently got a pair of Cross Point socks from Portland’s Showers Pass, a great PNW brand. They have a waterproof membrane sandwiched between two layers of soft material that keeps cold water away from your feet.
- Rain Booties are like galoshes for biking. I have two pairs: a set of snug rubberized Endura Luminate overshoes that slip over my click-in road biking shoes and a pair of zip-on Club Waterproof Shoe Covers from Showers Pass to wear over my sneakers or casual shoes when commuting to the office.
- Fenders are crucial in winter, and they come in many types. Some are easily installed and removed, such as the Raceblades from SKS that mount with quick-release straps. Others can be permanently mounted with hardware, such as the Full Metal fenders from Portland Design Works that I keep on my winter commuter.
- Bar Mitts: These voluminous neoprene mittens attach to your handlebars like a big, comfy oven mitt. I wear a thin glove underneath when it’s frigid or go barehanded inside when it’s just chilly.
- Bike Lights won’t keep you warm but will keep you safer. There are two basic types—lights for seeing and for being ) seen. I recently acquired a 700-lumen rechargeable City Rover headlight from Portland Design Works to light up the road in front of me. For visibility by drivers behind me, I attach a red USB taillight.
My final tip: be opportunistic. When the clouds break, get out there. Dark winters can dampen my mood. That’s why I make daily outdoor activity—whether bicycling, skiing, or just suiting up and walking in the rain—an intentional practice because there is no greater gift to give oneself than the resolution to move through winter with joy and reverence for the natural world.
Paul Tolme, the Journalist on the Loose, is an outdoors writer, award-winning environmental journalist, and blogger for Cascade Bicycle Club. He lives with his wife in a Seattle houseboat crammed with bikes, skis, snowboards, kayaks, and paddleboards, but no regrets. His work can be seen at paultolme.com and cascade.org/news.
