Chilly Hilly: Camaraderie, Views, Hot Food, and Hills
A woman rides past the Puget Sound on Chilly Hilly

The 48th annual ride around Bainbridge Island on Feb. 23 kicks off Cascade’s 50th anniversary. “It’s a great way to meet people and make new friends while challenging yourself in a beautiful location.”

As a commercial airline pilot, Laura Nealon has a flexible work schedule that allows her to participate in many bicycling events and big group rides. One of her favorites is Chilly Hilly, a 33-mile ride famous for steep hills and cold climates around Bainbridge Island in late February.

“It’s a great start to the riding season and encourages you to get out and ride when you otherwise might not,” says Nealon, 40, of Ballard. “You never know what you are going to get for weather. It could be cold and rainy or dry and sunny, but it is always super fun regardless.”

This year marks the 48th edition of the Chilly Hilly, which will be held on Sunday, Feb. 23. As Cascade Bicycle Club marks its 50th anniversary in 2020, the Chilly Hilly is an opportunity for people to ride in one of the organization’s oldest and most iconic events. Online registration closes on Feb. 19 at 11:59 p.m.; day of registration is available for $20 extra.

The Chilly Hilly begins with a ferry ride (free for registrants) from Seattle to Bainbridge, whereupon thousands of participants disembark together in a mass start. “The ferry ride is a really fun way to start the day. It’s a nice communal experience,” Nealon says. “Then it’s kind of magical when you get to Bainbridge, where you leave behind the urban environment and enter a beautiful, rural landscape with big trees and great views.”

Those views can include majestic Mt. Rainier covered in snow, the Seattle city skyline, the rolling Cascades, and the waves of the Puget Sound lapping at the Bainbridge shoreline. But as is typical for the Pacific Northwest, the weather can range from 25 and drizzling to 65 and sunny, so it’s best to be prepared.

True to its name, the Chilly Hilly has 2,173 feet of elevation gain. Nealon, who has ridden Chilly Hilly three times, loves the challenge of conquering the hills, which she describes as “fairly short but steep.” The hills do offer one benefit: “If it’s chilly out you really warm up,” she says.

With up to 5,000 participants, the Chilly Hilly is highly social. “You are never alone. People are talking and having a good time throughout the ride,” says Elizabeth Ozimek, a board member of Squeaky Wheels, the Bainbridge Island bicycle advocacy group that partners with Cascade to organize the Chilly Hilly.

Ozimek is a volunteer coordinator for the event, and she can be seen pedaling sections of the route pulling a trailer loaded with muffins, hot coffee, and warm drinks that she serves to volunteers working the rider aid stations. Many of the volunteers are bicyclists themselves who would prefer to be riding, “so they really appreciate a pastry and hot drink,” says Ozimek.

While riding 33 miles up and down hills may seem daunting to beginners, Ozimek says many participants hop off their bikes and walk to the top of steep sections—no shame involved. “People should take as much time as they like,” says Ozimek, 35, a real estate agent who has lived on Bainbridge for a decade. “Some people ride fast and don’t stop. Others take their time and enjoy the camaraderie. I like that you can hop on and off your bike on different parts of the island and take breaks or have a coffee and a snack.”

The most highly anticipated stop is mile 15 at Battle Point State Park, where Bainbridge Island Girl Scouts serve free cookies and snacks, and the Bainbridge Island Rope Skippers, a local competitive jump rope team, give out hot baked potatoes with toppings. The food provides a boost for finishing the second half of the ride, although participants can also take a shortcut that trims off about 10 miles.

For Nealon, the finish line party is another highlight—a chance to meet other bicyclists and share stories from the day. Bainbridge Island nonprofits serve chili ($8 per bowl, with proceeds benefiting island nonprofit organizations) at the finish line party held at the Bainbridge Island Senior Community Center.

“You develop a lot of camaraderie with other riders,” says Nealon, Cascade Bicycle Club’s 2018 Volunteer of the Year. While she likes the fitness benefits of riding the Chilly Hilly, it’s the sense of community and camaraderie that she values most. “It’s a great way to meet people and make new friends while challenging yourself in a beautiful location.”


Learn more about Chilly Hilly and save $20 by registering before the Feb. 19 online deadline:

Ozimek encouraged anyone interested in volunteering to contact her at 

Paul Tolmé's picture
Paul Tolmé