Our 5 Favorite Events on Bainbridge Island


Bainbridge Island hosts a variety of annual events for locals and visitors alike. Some speak to our small-town charm while others are huge hits and packed with people from all over. Here are five of our favorites.

Rotary Auction & Rummage Sale

July 2, 2022 at Woodward Middle School

We love this event for so many reasons. It signals the start of summer on the island with a charitable event that brings the community together to volunteer and give. One of Sarah’s personal favorite pieces of art is a painting she purchased for $30 at the rummage sale. This July will mark the event’s 62nd anniversary.

Bainbridge Gardens Pumpkin Walk

October 1st – 31st at Bainbridge Gardens

The creativity of the pumpkins donated for this event is amazing! For almost 30 years, locals and visitors have strolled Bainbridge Gardens’ nature trail during the Pumpkin Walk. The trail is lined with hundreds of painted and carved pumpkins. You can submit your own pumpkin to add to the walk and many people do. On the weekends, live music and food trucks are usually part of this festive, fall event.

Halloween Walk

October 31st in Downtown Winslow

From the congregational church’s spooky organ music to the teachers scooping (free!) ice cream at Mora to raise funds for Bainbridge Island Schools Foundation, to seeing all the costumes, this event cannot be missed. The Halloween Walk closes down Winslow Way, giving kids a chance to get candy from local shops and restaurants. It’s the perfect way to celebrate the holiday.

Bainbridge Island Turkey Trot

Thanksgiving Day, location TBA

Running in turkey costumes – what’s not to love? Some dear friends started the Turkey Trot and in its first few years, Sarah Sydor helped mark the course the afternoon before the race. There’s a 1-mile or 5k option, and it costs $20+ per person. You can check their event website for more information as Thanksgiving nears.

Polar Bear Plunge

January 1st at noon at Lytle Beach Public Park

What a way to start off the new year, jumping into freezing cold water with your family and friends! Someone creates a makeshift hot tub, and there’s always a crowd of supporters with towels and hot drinks. Join in the fun or cheer on others. The Polar Bear Plunge is a unique, memorable Bainbridge Island event.

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Kara Wyman

About Me

A Personal Approach to Bainbridge Island Real Estate

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