Things to Do in Healdsburg, CA
in September 2026
Wine country at its finest — the hills go gold, the grapes reach their peak, and the valley comes alive.
September Events
Jeffrey Halford & The Healers
The Elephant In the RoomKick off the month with an energetic roots rock performance from Jeffrey Halford & The Healers at this beloved Healdsburg pub. Raw guitar, honest storytelling, and the kind of show that makes a Thursday night feel like a Friday.
Live MusicLet's Crush It! A Harvest Celebration
Wetzel Family EstateExperience the hands-on magic of harvest season with grape picking, old-school grape stomping, and a barbecue lunch at the Wetzel Family Estate. This is the kind of event that makes you feel the season in your boots — literally.
Wine & HarvestBEE in Kenya Benefit Dinner & Art Auction
Dragonfly Farm and FloralA Kenyan-inspired family-style dinner, a honey-tasting station, and an art auction combine for one of Healdsburg's most distinctive evenings of the year. All proceeds support the BEE in Kenya initiative. Expect community warmth, global flavor, and genuinely meaningful evening.
Benefit EventSmall Vines Dinner at Hazel Hill
Montage HealdsburgAn intimate five-course seasonal dinner paired with estate-grown Pinot Noir in the stunning setting of Montage Healdsburg's Hazel Hill restaurant. For those who take food and wine seriously, this one belongs on the calendar.
Wine DinnerLive Music with S.R. Laws
Spicy Vines WineryAn evening of intimate acoustic storytelling and roots performance at Spicy Vines Winery. S.R. Laws brings the kind of set that pairs perfectly with a glass of something local and a seat in the vineyard air.
Live MusicRavi Coltrane Quartet Centennial Celebration
Raven Performing Arts TheaterA special Healdsburg Jazz event honoring the 100th birthday of John Coltrane, performed by his son Ravi Coltrane and his quartet. This is a landmark jazz performance in an intimate venue — the kind of show that people talk about for years.
Jazz & Live MusicAccess Alexander Valley Wine Week
Alexander Valley Region-WideA full week of immersive experiences across Alexander Valley's historic estates: tours of cave vintages, blender events, barrel tastings, and access to properties that rarely open their doors to the public. This is a week-long deep dive into one of California's most storied wine regions.
Wine & HarvestBrass Queens Live
Little SaintA high-energy brass band performance at Little Saint — Healdsburg's beloved plant-forward restaurant and venue. Brass Queens brings a sound that's bold, joyful, and impossible to sit still through. A great mid-week show if you're in town for Wine Week.
Live MusicHealdsburg Arts Festival
Center Street, HealdsburgFine art, handcrafted jewelry, and one-of-a-kind works from regional creators line Center Street for this annual celebration of the local arts community. Browse, buy, and discover makers from across the North Bay.
Arts & CultureFesta d'Autunno at HANNA Winery
HANNA Winery, Alexander ValleyTaste new Italian varietal wine releases from HANNA Winery alongside an artisanal spread of locally sourced food in this autumn-inspired celebration. A refined and festive close to a packed September weekend in wine country.
Wine & Dining
Event listings on this page reflect publicly available information at the time of publication. Dates, times, locations, ticket prices, and event details are subject to change or cancellation without notice. Healdsburg‑CA.com is not affiliated with event organizers and is not responsible for changes, postponements, or inaccuracies in event listings. Always confirm details directly with the venue or event organizer before making plans. Some events may require advance tickets or reservations.
