Biking on Bainbridge: Plan for the Chilly Hilly in February

If you’ve yet to conquer the Chilly Hilly, let’s get your biking on Bainbridge Island adventure on the books! When you leave your car behind, you can relax knowing that the ferry dock is a breezy ride from everything in downtown Winslow, and you’ll be perfectly poised to explore the bounty of Bainbridge Island’s winding roadways and forested trails. The Chilly Hilly Race takes you on a stunning 33-mile loop of the island—exploring the waterfront beauty of the south and the wooded parks of the north. 

If you’re unfamiliar with the Chilly Hilly Bike Ride, it’s an annual Bainbridge Island tradition. Biking on Bainbridge is challenging with substantial elevation gains (a total of 2700 feet on this ride), hence the “hilly” name. The race began in the late 1970s with around 100 riders, and now, each year, more than 5,000 cyclists come to climb these hills in the (most likely) pouring rain. The Chilly Hilly begins on the Seattle side, and it’s quite a sight to see these thousands of bikers riding onto the car ferry deck. 

While heading over for the Chilly Hilly, which has a recommended ferry departure, cyclists have no set boat to take back to the city. So why not plan ahead and stay on the island for a day or two to recoup and rest up after the ride? Allow yourself to relax at one of the best Bainbridge Island Hotels! The Eagle Harbor Inn is a boutique property, only minutes from the ferry and near all of the best things to do on Bainbridge, including restaurants, coffee shops, and so much more. Our elegant suites are dressed in Northwest decor, and you’ll love knowing you’ll have a warm and soft place to land after the Chilly Hilly. Book your room today! 

Biking on Bainbridge, plan now for the chilly hilly race in February

Biking on Bainbridge for the Chilly Hilly Race this Year

Biking on Bainbridge is a popular pastime all year round, but the Chilly Hilly is the biggest cycling event of the year! In fact, Bicycling Magazine named the Chilly Hilly “One of Four Classic Rides” in the nation. Here are a few things to know about the Chily Hilly this year: 

  1. The Chilly Hilly race begins at the Coleman Ferry Dock in downtown Seattle—though you can also start on the island side. If you choose to begin in Seattle, your registration fee includes your ferry fare. 
  2. The route is 33 miles long with two shortcut options—Cascade Bike Club runs the event and recommends waiting for the day before to download the maps for the path. However, the road will be marked with navigation along the way. There are plenty of tents to stop off for a water break, snacks, and rest. 
  3. Biking on Bainbridge can be challenging; some areas have narrow, if non-existent, bike lanes. And there’s a reason why the Chilly-Hilly gets its name—this race does include some substantial climbs, but the stunning Seattle skyline views, lush, misty forests, and beautiful beach scenes are worth the hard work. 
  4. The Chilly Hilly is always the last Sunday in February; this year, the event falls on February 25th, 2024. Head here to register.

There are many excellent options for keeping your rig in tip-top shape for biking on Bainbridge Island; here are the top bike shops for gear: 

  1. B. I. Cycle: This longtime cycling shop has been servicing the island for decades, offering bike and gear sales, fittings, and repairs. This bike shop is two blocks from our Bainbridge Island hotel. 
  2. Classic Cycle: For a complete inventory of new and used bikes, as well as repairs and other gear, check out this stalwart bike shop on the island. 
  3. Bike Barn Rentals: This seasonal bike rental company is open after Memorial Day weekend for your biking on Bainbridge Island needs. 
Biking on Bainbridge, plan now for the chilly hilly race in February

One of the Best Bainbridge Island Hotels for the Chilly Hilly

Biking on Bainbridge Island is an excellent way to get around and exercise during your getaway, especially if you’re lodging at one of the best Bainbridge Island hotels. The Eagle Harbor Inn is just a quick bike ride from the ferry dock in downtown Winslow. There’s plenty of space for bike storage, and you’ll love heading out on bike rides from the inn. 

We offer exceptional and beautifully designed overnight accommodations in five one-of-a-kind hotel rooms and two custom townhomes—built around a garden-filled courtyard. The spacious guest rooms are ideal for couples or solo travelers. Every guest room is fully equipped with luxurious amenities, en suite baths, and fine-quality furnishings. The townhomes are perfect for a small group, family, or friends getaway. They have full kitchens, and seating areas with cozy fireplaces, and are the perfect place to relax after the Chilly Hilly or any of your biking on Bainbridge Island adventures.

You’ll find hot coffee in the lobby each morning from our neighboring cafe, Pegasus Coffee—pop there for pastries, breakfast sandwiches, and lunch throughout the day. We also offer our guests other perks like passes to the local gym and much more. We can’t wait to host you this year! Plan ahead for the Chilly Hilly and book your lodging at one of the best Bainbridge Island hotels today! 

Scroll to Top