The Week Ahead
September 29, 2025
Return to Full Calendar
Autumn has arrived on Bainbridge Island, and with it comes a burst of color, cooler air, and an irresistible lineup of seasonal events that make this one of the most exciting times of year to explore our island. Whether you’re a long-time resident or a first-time visitor, this week offers the perfect excuse to get out and savor the sights, sounds, and flavors of the season. From a whimsical garden scavenger hunt to a month-long celebration of jazz and an inaugural Oktoberfest brimming with Bavarian spirit, Bainbridge is serving up something for everyone.
This is the time of year when the island feels especially magical. The maples are blazing red and gold, the air smells of woodsmoke, and the cozy cafes hum with conversation. But the real magic happens when neighbors and visitors come together to celebrate what makes this place so special. Our community has a knack for blending natural beauty, culture, and creativity into unforgettable experiences — and this week is a perfect example.
First up is Bloedel Reserve’s Annual Squash Hunt, a beloved family tradition that turns the gardens into a fall-themed adventure. Imagine crunching through leaves on winding trails as you search for brightly colored squash hidden among the foliage. Kids can pick up a Passport booklet, collect rubbings at each stop, and leave with a handmade keepsake of their journey. Add in hay bale climbing, pumpkin games, and a community pumpkin-painting contest, and you have a day of autumn fun that’s perfect for all ages.
For those seeking an evening of culture and creativity, BIMA’s Within/Earshot Jazz Festival 2025 offers a month-long celebration of one of America’s most iconic art forms. This isn’t just a series of concerts — it’s an immersive experience that brings together musicians, storytellers, and visual artists to explore jazz’s past, present, and future. Whether you’re a devoted jazz fan or just curious, the performances are intimate, thought-provoking, and filled with the kind of improvisational magic that can only happen live.
And then there’s the newcomer — Bainbridge Island’s very first Oktoberfest. This brand-new event promises to bring the island together for a day of German food, local beer, live music, and friendly competitions. It’s a chance to don your lederhosen, raise a stein, and dance to the sound of a traditional band, all while enjoying the island’s beautiful fall backdrop.
Taken together, these three events capture the heart of Bainbridge in autumn: nature, art, and community coming together in joyful celebration. Whether your idea of a perfect fall day involves a garden stroll, a night of world-class music, or a lively festival, this week has it all. So grab a sweater, rally your friends and family, and make plans to enjoy everything Bainbridge has to offer. This is one week you won’t want to miss.
Featured Events:
Return to Full Calendar
Squash Hunt
Fall has officially arrived on Bainbridge Island, and there’s no better way to savor the season than by joining the Annual Squash Hunt at Bloedel Reserve. Running from October 1 through October 31, this family-friendly tradition transforms the Reserve’s already spectacular trails into a whimsical autumn treasure hunt.
Upon arrival, guests can pick up a map at the Gatehouse and set off on a colorful adventure. Scattered throughout the gardens are decorative squash of all shapes and sizes, tucked into unexpected spots and waiting to be discovered. The crisp air, fiery fall foliage, and peaceful pathways make for a perfect seasonal outing — whether you’re a local or visiting for the weekend.
Young adventurers get a little something extra: a Passport, a charming nature-themed rubbings booklet available at the Arrival Garden. As kids find each squash display, they can make a rubbing in their booklet, creating a one-of-a-kind souvenir of their fall adventure. This interactive activity turns the hunt into an educational journey through nature’s autumn wonders, making it a hit for families with children.
The fun doesn’t stop with the hunt. Guests are invited to explore the Sheep Sheds, where climbing hay bales, posing for pictures on the classic tractor, and playing pumpkin-themed games like tic-tac-toe and checkers add to the festive spirit. It’s the perfect spot to slow down, laugh, and snap a few seasonal photos for the memory books.
If you’re feeling creative, plan to attend Welcome Wednesday on October 1 (1–4 PM) or October 4 (10 AM–1 PM) for pumpkin painting. Your finished masterpiece will be entered into the Reserve’s Pumpkin Contest, with all entries displayed throughout the month. Visitors can vote starting October 7, and the winner will receive either six guest admission passes or a complimentary Friends & Family Membership — a perfect excuse to return and enjoy the Reserve year-round.
All Squash Hunt activities are included with the price of admission, and timed tickets are recommended to ensure a smooth experience. Whether you’re looking to connect with nature, entertain the kids, or simply soak in Bainbridge Island’s autumn charm, this event promises a delightful day for all ages.
Cost, tickets and logistics:
Wednesday, October 1, 1-4pm
Bloedel Reserve, 7571 NE Dolphin Dr, Bainbridge Island, WA 98110
Full details here
Return to Full Calendar
BIMA's Within/Earshot Jazz Festival 2025
October on Bainbridge Island is about to get a whole lot more musical. The Bainbridge Island Museum of Art (BIMA) once again partners with Seattle’s renowned Earshot Jazz to present the Within/Earshot Jazz Festival 2025, one of the Pacific Northwest’s most anticipated cultural events. Earshot Jazz is widely respected for its year-round commitment to cultivating a thriving jazz community—supporting artists, pushing creative boundaries, and preserving the genre’s legacy. This collaboration brings that mission to life right here on the island.
For the entire month of October, BIMA’s Frank Buxton Auditorium becomes an intimate performance space where audiences can experience jazz in its many forms. But this isn’t just a concert series—it’s a full-spectrum arts experience where music, storytelling, and visual art come together. The festival is designed to spark conversation, encourage exploration, and deepen our understanding of jazz as both a historical tradition and a living, evolving art form.
Each week, the festival lineup features a mix of performances that capture the genre’s diversity. Expect to hear everything from high-energy swing reminiscent of the speakeasy era to cutting-edge improvisational sets that push the boundaries of sound. Brazilian rhythms weave through certain performances, bringing lush textures and infectious energy, while Northwest-based artists showcase the region’s unique jazz voice, proving that this art form continues to grow and thrive.
Beyond the music itself, Within/Earshot emphasizes storytelling—inviting audiences to reflect on the cultural, political, and social dimensions of jazz. Some events pair performances with talks or panel discussions, offering a behind-the-scenes look at the creative process and the ways jazz has shaped, and been shaped by, history. For visual art lovers, the festival often complements performances with curated exhibitions, allowing guests to engage with jazz not only through the ear but also through the eye.
Whether you drop in for one unforgettable concert or plan to attend multiple nights, this festival promises an immersive experience that connects generations and communities. Jazz newcomers will find an accessible entry point, while longtime fans will appreciate the festival’s commitment to both tradition and innovation.
If you’re looking for a way to warm up your October nights with world-class artistry, mark your calendar for BIMA’s Within/Earshot Jazz Festival. It’s Bainbridge Island’s chance to join in a citywide celebration of jazz’s enduring power to move, challenge, and inspire.
October 3-25
Bainbridge Island Museum of Art, 550 Winslow Way E, Bainbridge Island, WA 98110
Full details here
Return to Full Calendar
Bainbridge Island Oktoberfest
This fall, Bainbridge Island is getting its very own Oktoberfest, and it promises to be a celebration worth toasting! The inaugural Bainbridge Island Oktoberfest is set to bring Bavarian flavor to the Pacific Northwest with a day full of great food, local drinks, live music, and plenty of festive fun for all ages.
At the heart of the event is a delicious spread of traditional German fare—think bratwurst sizzling on the grill, warm pretzels with mustard, and hearty sides perfect for pairing with a cold drink. Local breweries and cideries will be on hand to pour pints of their best seasonal offerings, and wine lovers won’t be left out either. With so many choices, everyone can find the perfect drink to raise in a cheerful “Prost!”
Beyond the food and drinks, Oktoberfest is all about community and celebration, and Bainbridge is embracing that spirit with games, contests, and crafts. Expect to see friendly competitions such as stein-holding challenges, yodeling contests, and maybe even a costume parade for those who come dressed in lederhosen or dirndls. For families, there will be kid-friendly activities and creative crafts to keep younger festivalgoers entertained, making this a true all-ages event.
No Oktoberfest would be complete without lively music, and Bainbridge’s first outing is bringing in a traditional band to keep the energy high. The sound of accordions, brass, and festive tunes will fill the air, inviting everyone to dance, clap, and sing along. Whether you’re tapping your feet from the beer garden or leading a polka line, the music will set the tone for an unforgettable day.
This inaugural event is more than just a party—it’s the start of a new island tradition. With its mix of local flavor and Old World charm, Bainbridge Island Oktoberfest is poised to become a fall favorite for years to come. It’s the perfect excuse to gather friends, enjoy the crisp autumn weather, and celebrate community island-style.
So put on your best Bavarian attire, grab your stein, and head out to experience Bainbridge Island’s first-ever Oktoberfest. Great food, great music, and great company await—you won’t want to miss this one.
Cost, tickets and logistics:
Saturday, October 4, 2-8pm
Bainbridge Island Rowing 281 Brien Drive Southeast Bainbridge Island, WA 98110
Full details here
Return to Full Calendar
Ready to Make A Move?
Our team is committed to helping you achieve your real estate goals. Connect with us to receive a free consultation to learn about your options in today’s market and see how our executive package is the only way to maximize your ROI. With my background as a Marketing Executive, you’ll get custom market analysis and ongoing tracking, video story-telling with A/B tested marketing messaging, catered open houses, staging and design, and so much more.
With over $100M of real estate sold, ranked in the top 1% of realtors nationally, and voted #1 Best Realtor on Bainbridge Island in 2021 and 2022, I know what it takes to craft the perfect offer and land your forever home. I’ve had the honor of serving over 100 families in Bainbridge Island, Greater Seattle Area, the Eastside and beyond. Properties include single and multi-family homes, condos in both the busy city and calm suburbs, waterfront homes with exceptional views, estate listings, and investment homes anywhere from a couple hundred thousand to a million dollars–each property receives the same concierge experience.
Let us help you buy or sell your home. Reach out to our team today to get started.
