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Healdsburg
October 29, 2026

Things to do in Healdsburg, Oct. 22-27

Rick Tang photo
It’s called the Howl-o-Ween Pet Parade (get it?) and both pets and their people look forward to this annual free event designed to generate good times and donations to the Humane Society’s Pet Food Pantry. Plus more goings-on this weekend and next week...

Plaza reclaims its place as Healdsburg’s hub

Returning for its 10th year is Dia de Muertos, the Mexican folk holiday that has found a new home north of the border since 2016. Dia de Muertos was first recognized locally to mark Corazón’s inaugural community event, where it introduced the newly established organization to Healdsburg.

Cruise chews the scenery in ‘Digger’

A howlingly angry attack on the politicians who spitefully whistle their way past the graveyard as they find new ways to destroy the climate, individual freedoms and humanity as a whole...

Things to do in Healdsburg, Oct. 15-22

Bluegrass jam on Friday from Electric Tumbleweed ($15), reggae on Saturday with Sol Horizon ($20) at the Elephant in the Room. Plus more events coming up this week...

Crushing it once again for the B&G Clubs

Winetasting at Healdsburg Crush!
In winemaking, “crush” is not only an act essential to the art and industry of viticulture, but a term for the seasonal turn from growing to winemaking, of harvesting the grapes and releasing their juice and pulp so fermentation can begin. In Healdsburg, it's a seasonal winetasting celebration, held this year on Oct. 11.

How Peptoc won the internet

One of the most viral web phenomeon of late was Peptoc—a phone line that anyone can call and get a “pep talk” from Westside School students. It’s a public arts project, created by Jessica Martin and Asherah Weiss when their teaching careers overlapped at the small public school just outside Healdsburg.

Cyrus Chestnut in concert from Healdsburg Jazz

Expect plenty of seasoned authenticity when Cyrus Chestnut and a local rhythm section, Jaimeo Brown on drums and Marcus Shelby on bass, hit the Paul Mahder Gallery stage in Healdsburg on Sunday, Oct. 11, at 7pm.

Things to do in Healdsburg, Oct. 8-15

Healdsburg has certainly become a live music town; one can tune in almost any day of the week. Saturday afternoon check out Spicy Vines, a tasting room and living room-style venue for folk, jazz and other artists, usually with no cover...

Open up to Healdsburg Design

Starting concurrently with this week’s Art Nite on Thursday is the return of the four-day Design Healdsburg, produced by Design Bay Area. It’s in a class with similar North Bay Design weekends in San Francisco and Marin, and once again Healdsburg claims a strong...

Things to do in Healdsburg, October 1-8

Healdsburg Indivisible brings the award-winning documentary and political thriller Dark Money to town, which “uncovers the shocking and vital truth of how American elections are bought and sold” on Oct. 8.
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Arts & Entertainment

Dia de Muertos lives on in Healdsburg

At Dia de Muertos—Healdsburg’s most colorful event of the year, recognized Sunday, Oct. 25 at the Plaza—Sonoma County residents showed up to remember loved...