Things to Do in Windsor, CA
in September 2026
Early fall is hitting Windsor’s stride. Here’s your full September guide.
September arrives in Windsor with the first honest whisper of fall: mornings carry a new crispness, the vineyards around town begin to blush with color, and the community exhales after the long push of summer. It’s one of the best months to be here. Festive enough to fill your calendar, still warm enough to make every outdoor moment count. From chili cook-offs and cultural celebrations to hands-on workshops and evenings of local wine and live music, here’s everything worth circling on your September calendar.
Michael A. Hall Park Beautification
Join local volunteers for a community effort to maintain and improve one of Windsor’s beloved green spaces. All skill levels and ages welcome. Bring gloves, show up, and help keep the park looking its best as fall settles in around us.
13th Annual Windsor Chili Cook-Off
A Windsor tradition now in its 13th year. Taste competing chili entries from local pitmasters, cast your ballot for the People’s Choice winner, and catch live country music from Dustin Saylor rolling across the Town Green all afternoon. The perfect warmup to fall season.
Sip, Sort, Win – Speed Puzzle Competition
A casual, competitive evening pairing speed puzzling with local Sonoma County wine pours. Race the clock while the crowd cheers you on. If you’ve been looking for a fun way to kick off the weekend, this is it.
Wash Day at Hembree House
Step back in time with this family-friendly, hands-on historic laundry demonstration using vintage washboards and wringers at the Hembree House Cultural Center. Free and all ages welcome. A genuinely charming way to connect with local history and a great activity to bring the kids to.
Native Plant Seed Propagation Workshop
Hosted in partnership with the Habitat Corridor Project, this workshop teaches practical techniques for starting your own home native plant nursery from seed. As fall transitions the landscape, it’s the perfect time to plan what you’ll be growing come spring.
Downtown Windsor Locals Day + Sidewalk Sale
A day built for Windsor residents. Shop exclusive retail deals, enjoy restaurant specials, and pick up a Locals Passport to work through participating downtown businesses. A real reason to shop local and support the shops that make Windsor what it is.
El Grito de Windsor & Hispanic Heritage Celebration
A vibrant, community-driven cultural event hosted by Somos Windsor and the Town of Windsor to open Hispanic Heritage Month. The Town Green comes alive with music, food, and community around the annual El Grito tradition. One of Windsor’s most spirited evenings of the entire year.
Is Your Windsor Business Easy to Find Online?
TIV360 has been building and optimizing WordPress sites for Sonoma County small businesses since 2008. No outsourcing, no account managers. Just real results from a local operator who knows this market.
Get Found Online at TIV360.comSips & Succulents – Vintage Teacup Garden
Spend Sunday afternoon crafting a miniature succulent garden inside a vintage teacup while sipping local Sonoma County wine. Part creative workshop, part wine tasting. A relaxed, unhurried way to ease into fall while making something you’ll actually keep.
Windsor Day Parade & Festival
Windsor’s signature annual celebration returns. The traditional parade rolls through town featuring local community groups, floats, and live music, followed by family activities on the Town Green. This is the event September has been building toward. Mark it, show up, and bring the whole family.
Live Music with Callie Watts
Cap off Windsor Day weekend with an intimate singer-songwriter performance from Callie Watts at the Wine Lounge Collective. Unhurried, live, and local. An evening of original music, Sonoma County wine, and good company – the right way to close out September’s biggest weekend.
Events Disclaimer
Event details on this page, including dates, times, locations, ticket prices, and availability, are gathered from public sources and reflect information available at the time of publication. All events are subject to change, cancellation, or postponement without notice. Windsor-ca.net is not affiliated with, endorsed by, or responsible for any event listed on this page. Please verify current details directly with event organizers before attending.
