The Raven Theater Is About to Have Its Busiest Week of the Year

"If music was a religion Bill Frisell would be a Saint," the composer John Zorn once said of the guitarist. Frisell is not a name most people driving down North Street would expect to see on a marquee in a wine country town better known for tasting rooms than jazz royalty. But on September 29, he's playing the Raven Performing Arts Theater with his Harmony Five lineup, cellist Hank Roberts and vocalist Petra Haden among them, as part of a run of 75th-birthday shows that has already stopped in San Francisco and New York.

What makes that booking interesting isn't the show itself. It's that Frisell's Tuesday night at the Raven is the fourth act in a five-day stretch that starts four nights earlier, when the Healdsburg International Short Film Festival opens its fifth year on the same stage. In between, the Healdsburg Center for the Arts runs its own festival a few blocks over on Center Street. For one week, three separate organizations are drawing national-level talent into a four-block radius of the Plaza, and almost none of it has anything to do with wine.

Five Days, One Stretch of Sidewalk

Here's how the week actually lays out:

The short film festival runs its full three days at the Raven, a 350-seat house that has hosted decades of local performances and premieres. It opens with a red-carpet screening and closes with an awards presentation, the same structure it has followed since it moved from its original home in Bodega Bay. The Center for the Arts' Festival of the Arts lands squarely in the middle of that run, on Saturday the 26th, its own long-running end-of-summer event now sharing a weekend with the film festival by design rather than coincidence. The two organizations built HISFF's fifth year in collaboration specifically so the two events would overlap.

Why the Same Names Keep Showing Up

A festival's jury list is usually the least interesting part of its marketing copy. This one is worth reading closely, because it tells you something about how the town operates that a tourism brochure won't.

Ed Begley Jr. is judging HISFF for the fifth year in a row, meaning he has judged every single edition since the festival began. Billy Ray, who wrote the Oscar-nominated screenplay for Captain Phillips and co-wrote the first Hunger Games film, is back for his second year, and he's doing a book signing at the Raven on Saturday the 26th, timing still to be announced. Jeff Kober, an Emmy nominee this year for his role in The Pitt, is also returning for a second year. Laraine Newman, an original Saturday Night Live cast member and co-founder of the Groundlings Theatre, is on the jury as well.

That pattern of returning judges is the real story. A one-off festival with a decent prize purse can usually book a recognizable name once. Getting the same people to come back year after year means they found something worth repeating, and the festival's own materials are fairly direct about what that is: filmmakers who screen at HISFF get put up with local host families rather than in a hotel block, and the weekend is built around Sonoma County itself, not just the theater seats. The festival is currently looking for more volunteer households willing to host traveling filmmakers this September, which tells you the hospitality side of this event is still running on neighbors, not a corporate housing budget.

The festival's founders also run the original Bodega Bay International Short Film Festival, and between the two events they've now screened more than 255 short films from 50 countries, including Academy Award winners and Cannes Special Distinction honorees. Healdsburg didn't inherit that reputation. It built it over five years, one returning juror at a time.

The Saturday You'll Have to Split

If you only have one day that week, September 26 is the one with a scheduling problem. The Festival of the Arts is running on Center Street. HISFF has screening blocks at the Raven. Billy Ray's book signing is happening somewhere in that same window. Last year's festival ran its Saturday programming across a full day, from a late-morning student film block through an afternoon mixed-genre screening and into an evening filmmaker mixer, so if this year follows a similar shape, Saturday is genuinely the day you'll need to pick a lane rather than try to catch everything.

The festival's own site currently lists tickets and full scheduling as still coming, so exact start times for 2026 aren't locked yet. Last year's tier structure gives a reasonable sense of what to budget for: an all-access pass ran $175, a festival pass (which lets you pick your own mix of events) ran $100, and individual screening blocks were $20 general admission or $10 for students. If pricing holds close to that shape, a single afternoon at the Raven is a modest ask, and the full weekend is the kind of thing you plan for rather than decide on the day.

What This Means for Your Week

None of this requires travel, reservations made weeks in advance, or fighting Plaza traffic that ramps up for crush season events later in October. It requires knowing that the Raven's marquee is about to run five days deep and that three different local organizations, not one, are behind it.

If you're picking one thing to build a plan around, the Frisell show has the most certainty attached to it. It's a fixed date, September 29, a Tuesday, 7:30 to 9:00 PM, at the Raven. Everything else that week is worth checking the festival's own site for as details firm up, since the schedule isn't fully public yet.

What's actually notable isn't any single event on this list. It's that a town this size has built enough of a track record, five years of a growing jury list on one end and a touring jazz legend's milestone stop on the other, that this particular week now functions as an actual cultural season rather than a single festival weekend bolted onto the calendar.

If you're new to town, or you've lived here long enough that late September has always meant crush pace and nothing else, this is the week that quietly proves otherwise.

If a friend or family member is thinking about what it's actually like to live somewhere with a calendar like this one, not just visit for a weekend of tastings, Ceci Cook would be glad to talk through what Healdsburg living looks like beyond the festival posters. Let's connect.