A Chilly Hilly Preview–with Bainbridge Island Wine

  • Chilly Hilly presented by REI Co-op takes place on Feb. 25. We took the ferry to Bainbridge Island to sample segments of the route–and enjoy some apres wine.
  • Eleven Winery is a bike-loving vintner worth visiting whenever pedaling on Bainbridge.
Riding my electric cargo bike is my favorite thing

Paul Tolmé

Jessica Moskowitz pedals along Eagle Harbor Drive

On a gray morning in early February, I met up with a group of Cascade friends at the Bainbridge Island Ferry Terminal in downtown Seattle. 

All ready for Chilly Hilly!
Mangan, Pringle, Moskowitz and Prince.

Our plan was to ride portions of the 33-mile Chilly Hilly presented by REI Co-op course, and visit our sponsor Eleven Winery to sample their vintages.

Joining me were Cascade Rides and Events Director Allison Pringle, Instagram Influencer and Cascade Let’s Go Coordinator Shannon Mangan, and Cascade Outriders Jessica Moskowitz and Tim Prince.  

Temperatures were in the low 40s when we pedaled off the ferry in Winslow, a lovely seaside community where the Chilly Hilly route starts and ends. Due to limited time, we shortcut the route and pedaled the final segment of the course on the southern end of Bainbridge.

Shannon enjoys the separated bike lane that brings riders toward the finish.

The views along Eagle Harbor Drive, Blakely Harbor Park, and Pleasant Beach Drive were lovely, and despite intermittent drizzle the Bainbridge Island scenery reminded us why about 2,000 people are expected to ride Chilly Hilly on Feb. 25. 

Lots of farmhouse views on Bainbridge.

Eleven Winery

At noon we detoured off the route and pedaled to Eleven Winery on Day Road, where we had a lunchtime appointment to meet the founder. The Winery isn’t on the Chilly Hilly course, but it’s worth a side trip for anyone staying overnight on Bainbridge. 

Founded in 2003, Eleven is named for the 11-tooth rear cog on road racing bikes. Vintage bicycles decorate the interior walls of the winery. Founder Matt Albee is a former bike racer who has ridden Chilly Hilly more times than he can recall, sometimes pulling his children in a trailer for one lap–and then doing a second lap solo.

Eleven Winery founder Matt Albee

Eleven sponsors Chilly Hilly because Albee wants to support Cascade’s mission of improving bicycling for all. “Bainbridge Island is our home and we are a bike-related brand. Partnering with Cascade is a great way to support Chilly Hilly, connect with cyclists, and support bicycling here on Bainbridge.”

Eleven loves bikes so much that it offers 50 percent off wine tastings to anyone who arrives at their Day Road winery on a bicycle. And they offer free shipping on any bottles you buy.

Vintage bicycles adorn the interior of Eleven Winery

We took advantage of the deal to get a wine flight of sample pours. Eleven purchases all of its grapes in the wine growing regions of eastern Washington and Oregon, and it crushes, ferments, bottles and ages all its wines on Bainbridge. 

Route map of Chilly Hilly

Riding Chilly Hilly for the First Time?

  • Weather: Check the forecast and dress accordingly. Staying toasty on winter rides means dressing in layers and keeping your fingers and toes warm and dry. Bring a backpack, panniers, or hip pack to carry extra clothing. Chilly Hilly is a ride, not a race, so don’t worry about carrying a little extra weight.
  • Food: Cascade provides snacks at the midpoint lunch stop at Battle Point Park, and riders can buy vegan or meat chili at the finish celebration. Bring cash for chili purchases, which benefit the local senior center. Winslow also has many restaurants, markets, and dining options if you want to linger following the ride.  


One of the smaller hills on Chilly Hilly
  • Hills: The course lives up to its name. Stay right on climbs and be mindful that others may want to pass on your left. It's OK to walk your bike up a hill, just stay to the right. Chilly Hilly takes place on open roads, and while many locals know to avoid the course on Chilly Hilly day, there will be cars on the roads–plus about 2,000 riders. Be considerate of drivers and watch out for cars turning into or out of driveways.
  • Swag: Chilly Hilly T-shirts will be sold at the finish line in the Cascade tent. People love the orca design on the logo. Get one for yourself or a family member. All proceeds go to support Cacade’s programming. 


Order your Chilly Hilly shirt
Order your shirt here.

Cozy REI Camp Lounge at Finish

REI Co-op is the title sponsor for Chilly Hilly. At the finish line festival in Bainbridge Waterfront Park, REI will have a portable fire pit with camp chairs to relax and warm up. Stop by the REI tent to get a free Klean Kanteen steel pint cup.

Chilly Finishers can get coupons to the Eleven Winery tasting room in Winthrop in the Cascade tent, and Chilly Hilly sponsor Spinnaker Chocolates will give away chocolate samples to Chilly Hilly finishers.

Register for Chilly Hilly!

After a fun time at Eleven Winery, we pedaled back to Winslow and boarded the ferry back to Seattle–eager to return on Feb. 25. Chilly Hilly is an apt name for the terrain and typical winter weather, but this ride could also be called the Beautiful Bainbridge Island Scenic Tour. 

Tim cruises on Eagle Harbor Drive

Registration for Chilly Hilly presented by REI Co-op remains open until Thursday Feb. 22 at 11:59 p.m.

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