From autumn markets and local arts to neighborhood celebrations and Halloween traditions, discover what's happening around Lake Oswego this October. There is something special about October in Lake Oswego. The trees begin their annual transformation, mornings turn crisp, and the community settles into a season filled with familiar traditions and opportunities to connect.
Whether you're spending Saturday morning at the Farmers' Market, discovering a local artist, or making plans for Halloween weekend, October offers plenty of reasons to get out and enjoy the place we call home. Here are a few community happenings worth adding to your calendar.
1. Lake Oswego Wine Walk | A Toast to Community
Saturday, October 3, 2026 | 1:00–5:00 PM Downtown Lake Oswego
Raise a glass to community at the Lake Oswego Wine Walk! Spend the afternoon strolling through downtown, discovering local businesses, sampling thoughtfully selected wines, and enjoying the welcoming atmosphere that makes Lake Oswego so special.
Spears Property Group and our neighbors at Lake Oswego Coffee House & Wine Bar are excited to participate, welcoming guests to our corner at Second & B for an afternoon of wine, seasonal bites, and good company.
Our featured pours include:
Spears Property Group: Steenberg Sparkling Sauvignon Blanc from South Africa and COR Cellars Malbec from Washington.
Lake Oswego Coffee House & Wine Bar: AGO Sauvignon Blanc and COR Tempranillo.
Whether you're a longtime resident or discovering downtown for the first time, the Wine Walk is a wonderful opportunity to support local businesses and celebrate the community we call home.
Stop by, say hello, and enjoy a little taste of Lake Oswego with us!
2. Lake Oswego Farmers' Market
Every Saturday, October 3–31 | 8:30 AM–1:30 PM Millennium Plaza Park
A beloved Lake Oswego tradition continues through the end of October. Spend your Saturday morning exploring seasonal produce, artisan goods, fresh flowers, baked treats, and locally prepared foods.
With live music and familiar community faces, the Farmers' Market is a wonderful way to experience the changing season while supporting regional growers and small businesses.
3. Día de los Muertos Celebration
Sunday, October 4 | 1 PM
Celebrate culture, remembrance, and community at Lake Oswego's Día de los Muertos celebration. This gathering offers an opportunity to experience a meaningful cultural tradition and connect with neighbors.
4. Lake Oswego Film Festival Screening
Sunday, October 18 | 5:30–8 PM Lake Oswego Adult Community Center, 505 G Avenue
An evening dedicated to storytelling and independent filmmaking. This special screening showcases seven to eight award-winning short films selected by an international panel of judges, featuring documentary, narrative, animation, and music video genres.
Select filmmakers will attend, with an audience Q&A following the screening. Admission is free, and registration is not required.
5. Urban Forest Summit
Saturday, October 24 | 9 AM–12:30 PM Lake Oswego United Methodist Church, 1855 South Shore Boulevard
Lake Oswego's natural surroundings are an important part of its character. The eighth annual Urban Forest Summit brings neighbors and environmental organizations together for conversations about land restoration, habitat stewardship, and the community's relationship with its natural environment.
This year's theme, Stories of Transformation: Restoring Our Human Connection to the Land, includes films, presentations, and opportunities to connect with local environmental experts.
Admission is free; registration information is available through the organizer.
6. Monster Mash: Halloween in Lake Oswego
Saturday, October 31 | 2–5 PM Christ Church Parish, 1060 Chandler Road
Close out October with a family-friendly Halloween celebration hosted by Lake Oswego Parks & Recreation. Children ages 0–12 are invited to dress in their favorite costumes and enjoy trick-or-treat stations, Halloween crafts, music, and visits from the Lake Oswego Fire and Police departments.
This event is free, with complimentary trick-or-treat bags available for the first 400 guests while supplies last.
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More Than a Place to Live
What makes Lake Oswego special extends well beyond its beautiful homes and natural surroundings. It's the people, traditions, independent businesses, and shared experiences that give this community its character.
At Spears Property Group, our connection to Lake Oswego is personal. From our office at Second & B, we're proud to be part of the neighborhood and to share the places and experiences that make living here so meaningful.
Here's to crisp mornings, colorful afternoons, and another beautiful October in our community.
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