The Not-So-Chilly Hilly Scheduled for Sunday August 1, 2021 – Sunscreen Required!

The Chilly Hilly? In summer? Seriously?

For the first time in its history, the traditional kick-off ride to the Pacific Northwest biking season – held on Bainbridge Island for nearly five decades – will be staged in the summertime.

More specifically on August 1st – this coming Sunday. It looks like sunscreen and shorts will replace rain slickers and booties!

If you are interested in registering for the ride that Bicycle Magazine calls one of the Top 10 bicycling events in America, visit

The Chilly Hilly has been staged by the Cascade Bicycle Club for 49 years in cooperation with dozens of Bainbridge non-profits, who use the event to raise money and awareness for their organizations and causes, as well as lots of businesses that benefit from cyclists patronizing their shops and restaurants.

“Cascade had to cancel Chilly (Hilly) in February due to COVID-19 restrictions,” said Paul Tolme, the organization’s Content Strategy & Media Relations Manager, “and we sorely missed it. Along with (the) Chilly Hilly we had to cancel most of our in-person event calendar last year and (during) the first half of 2021.

“Cancelling our events was a bummer,” Tolme added, “not only because we enjoy seeing so many happy people out participating in our events, but also because these big events are how Cascade raises money for our advocacy and policy work pushing for more bike infrastructure, as well as our education programs and other good works we do in the community.”

Even if you’re just a spectator, the Chilly Hilly is a fun event to watch as hundreds of riders in colorful riding gear roll off the Bainbridge ferry and navigate a 33-mile course, with plenty of twists and turns, coupled with amazing vistas, and, of course, hills, lots of hills interspersed around our bucolic island.

As a long time island  bike rider, I know this course like the back of my hand, and the hills are what make the Chilly Hilly both challenging,  entertaining, and at times frightening and maybe a wee bit intimidating.

Let’s see, there are the hills of Rolling Bay along Sunrise Drive, Hidden Cove Road, Petersen Hill Road, – ugh – Arrow Point Drive, on the way to Battle Point Park, the infamous Baker Hill – where you might see a biker or two hopping off their stead and walking – Halls Hill, where on top the Labyrinth and Tibetan Prayer Wheel await you, the gradual but nasty hills along Eagle Harbor Drive, and finally the two hills on Wyatt Way that take you into beautiful Downtown Winslow.

By this time, your thighs might be burning and your bottom aching, and the want for a beer, glass of wine and a meal at one of our fine watering holes is finally in front of you.

Whew, no easy feat.

Over the years, I’ve ridden the Chilly Hill a dozen or more times, and it’s always a bit of a gut check. But it’s also a fantastic way to see the island, run into friends and support biking and a few local non-profits.

According to our friends from the Cascade Bicycle Club and our own observations, here are some highlights of the ride:

  • The “Devil’s Dip” on Arrow Point Drive. This is the Chilly Hilly’s steepest descent, while Baker Hill is the steepest climb.

  • Battle Point Park. For those with time to explore, the park has many ponds, trails, an astronomical observatory, and a playground.

  • Lynwood Center. About 25 miles into the route, this charming town center offers restaurants and shops serving beverages, baked goods, pizza, frozen yogurt, hamburgers, and more–as well as public art.

  • Halls Hill Labyrinth and Tibetan Prayer Wheel. Located at mile 27, and atop a climb, the mosaic labyrinth and bronze prayer wheel are tucked into a lovely pocket park.

  • The viewpoint at the intersection of Rockaway Beach and Eagle Harbor Drive, at about mile 28, provides photo ops of Seattle, Mount Baker, and ferries entering Eagle Harbor.

  • Manzanita Bay is a scenic public beach accessed via Dock Street at about mile 16.

  • Frog Rock, which is supposed to represent the island’s rural nature, is located at the corner of North Madison and Phelps Road.
  • Rockaway Beach Park is a favorite location for a selfie or quick dip, as well as a prime spot for exploring the island’s tide pools.

  • Downtown Winslow, the beginning and end of the ride for most participants, has shops, restaurants and a semi-urban vibe.

Tolme said race organizers are hoping for about 1,500 riders this year (there have been as many as 7,000 in years past) and hope to stage the event on its traditional February date in 2022.  We’ll keep our fingers crossed!

Click here for route map and cue sheet.

*Images and logos provided by Cascade Bicycle Club

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