1
Bike to the ferry dock to begin, just like they do for the famed Chilly Hilly, an organized 33-mile ride held every February, rain, snow or shine. You can also rent a bike right at the ferry terminal from Classic Cycle.
![Chilly Hilly. Bike & Kayak Itinerary, Bainbridge Island](https://www.bainbridgeisland.com/wp-content/uploads/2019/12/chilly-hilly-bainbridge-island.jpg)
2
About 16 miles in, you’ll hit Battlepoint Park. Happen to have a tennis racket strapped to your back? Lob a few balls while you’re there. Otherwise, take a walk around before getting back on the bike. The 3 miles of trails in the park are flat, and pass a pond where you’ll get to see ducks.
![Battlepoint Park, Bike & Kayak Itinerary, Bainbridge Island](https://www.bainbridgeisland.com/wp-content/uploads/2019/12/battlepoint-park-bainbridge-island.jpg)
3
Another nine miles and it could be time to refuel. Stop for pizza at the Treehouse Café and then grab a baked good for the road at Pane d’Amore right next door.
![](https://www.bainbridgeisland.com/wp-content/uploads/2019/12/pane-damore-bakery-bainbridge-island.jpg)
4
When you roll back into Winslow, after 33 miles and almost 3,000 feet gained, you’ll be right on track for the next event to begin. Check out a kayak at Back of Beyond and dig in a paddle at Waterfront Park.
![Waterfront Park, Bainbridge Island](https://www.bainbridgeisland.com/wp-content/uploads/2019/12/waterfront-park-bainbridge-island.jpeg)
5
Plan a few days ahead and line up a massage near enough to limp to. Advaya Wellness is on the main drag in Winslow — an appointment is needed. Or try Island Fitness — you can schedule ahead or drop by and hope a massage table’s open. –Cindy Jones
![Island Fitness, Bike & Kayak Itinerary, Bainbridge Island](https://www.bainbridgeisland.com/wp-content/uploads/2019/12/island-fitness-bainbridge-island.jpg)