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Best Bets for the 2024 Healdsburg Jazz Festival

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A black woman in a red dress sings into a microphone while tilting her head upward, eyes closed
Samara Joy will headline an opening weekend concert for the Healdsburg Jazz Festival on June 16 at Kendall-Jackson winery. (Gabriele Bifolchi)

As a Sonoma County resident and jazz fan, I’ve gone to the Healdsburg Jazz Festival nearly every year for the past 20 years. When the lineup drops, like it recently did for the 2024 festival running June 15–23, I make notated lists of what to see. What follows are my picks for the best shows to see among the formidable lineup.

But first: If you’ve heard about the festival but never attended, let me try to tell you what makes it special.

Take last year’s free show in the town plaza with Charles McPherson. Where else could farmworkers and wine tourists alike sit in the shade on the grass, listening to an 83-year-old jazz saxophone legend? Or last year’s tribute to Pharoah Sanders, with Gary Bartz and Sanders’ son Tomoki reverently playing “The Creator Has a Master Plan” under the stars and among the vineyards?

Over its history, Healdsburg has hosted up-and-coming talent, like Esperanza Spalding, who played in a restaurant’s backyard at the festival when she was brand-new on the scene. For several years, Santa Rosa-raised guitarist Julian Lage was a local opener at the festival, before he became a Blue Note recording artist who graces magazine covers.

And then, naturally, there are the legends. Past years have included Jackie McLean, Ron Carter, Kenny Burrell, Charles Lloyd, Geri Allen, Charlie Haden — the list goes on. In Healdsburg, these artists get the treatment and crowds they deserve, and in an unusually scenic, intimate setting. (I’ll never forget the year I literally bumped into drummer Andrew Cyrille in the cramped back kitchen of a coffee shop just off the downtown plaza.)

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This year, if you want to start easy, there’s the return of the Juneteenth in the Plaza concert on June 15, this year featuring trombonist Steve Turre with his sextet and soul-jazz saxophone veteran Houston Person. The plaza concerts (hosted by KCSM’s Greg Bridges) are among my favorites at the festival — they’re completely free, the grass fills up with all types of people, and the music blankets the entire downtown.

Billy Hart at the Healdsburg Jazz Festival, June 4, 2016.
Billy Hart at the Healdsburg Jazz Festival, June 4, 2016. (George B. Wells)

Want to go big? After a sold-out performance at last year’s festival, hot-streak vocalist Samara Joy will headline the festival’s opening weekend with a June 16 show at Kendall-Jackson winery. The cheapest seats are $125, but lawn seating is $35–$55 — and feels more befitting of a winery show, in my opinion.

Bacchus Landing’s outdoor courtyard, situated among the vineyards, is a relatively new venue for the festival; though the sun can heat the folding-chair seating, it’s hard to beat the cool open air after sundown. I have my eyes on rising vocalist Jazzmeia Horn, and her performance with festival director Marcus Shelby and his orchestra on June 20.

Also at Bacchus Landing is the remarkable Chief Adjuah (née Christian Scott) in a double bill with The Cookers (Cecil McBee, George Cables, Billy Hart, Craig Handy, Eddie Henderson, Donald Harrison Jr. and David Weiss) on June 21; the Joshua Redman Quartet featuring Gabrielle Cavassa on June 23; and Ambrose Akinmusire, Bill Frisell and Herlin Riley with opener the Brandee Younger Trio on June 22. Redman tends to shine in Healdsburg, and Younger blew my mind last month in San Francisco.

Cuban pianist Omar Sosa and his Quarteto Americanos will perform on June 17 at Healdsburg’s venerable Raven Theater, a charming former movie theater built in 1949. And then there’s the small shows scattered all over town. My picks would be Howard Wiley’s quartet at The Elephant in the Room on June 15, the Jazz Mafia’s “New Directions in Brass” at Spoonbar on June 19, and a tribute to Duke Ellington with Tiffany Austin at St. Paul’s Church on June 22.

As for food? Other people will be happy to gush about Healdsburg’s world-class dining and wine. I’m more likely to recommend the no-frills El Sombrero or Flakey Cream for lunch, and either Healdsburg’s Goodwill or a Russian River swimming hole for cheap thrills.

But for a week in June, at least, we can all agree on the music.


The 26th Annual Healdsburg Jazz Festival runs June 15–23, 2024, at various venues in and around Healdsburg. Details here.

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