Jake Shimabukuro will perform in Healdsubrg on Father's Day, June 15.
VIRTUOSO Hawaii-born Jake Shimabukuro has expanded the universe of ukulele playing with forays into jazz and blues, like his recent record with Mick Fleetwood. He’ll headline the Healdsburg Jazz Festival on June 15.

The Healdsburg Jazz Festival (HJF) seems as if it must be modeled after a film festival, with multiple venues offering different artists throughout the day. There are the featured events, sure–a Juneteenth Celebration, a Father’s Day Concert, headline shows at Bacchus Landing – but it’s the little gigs that count. 

A survey of the menu of musicians can easily turn into a fan’s tour of town, from Healdsburg grand to cozy, outside and indoors.

The Raven

Tyreek McDole at Healdsburg Jazz
DOUBLE DEBUT Vocalist Tyreek McDole looks for a way out of the blue box at the Healdsburg Jazz Festival, the same week his debut album ‘Open Up Your Senses’ will drop.

Opening night this year is at the Raven Theater (115 Plaza St.), which was always a favorite hall for HJF performers from the beginning (in 1999, when it was still showing movies). Dozens of posters of past concerts and plays decorate the walls of the classic 480-seat cinema hall, and the stage is set for NEA Jazz Master Kenny Barron on Friday, June 13.

The pianist and composer will play in the classic trio format, with Savannah Harris on drums (one of several female drummers in this year’s festival) and bassist Kiyoshi Kitagawa. Adding to the celebration is Tyreek McDole, a 25-year-old Haitian-American vocalist.

The Plaza

The next day is Saturday, June 14, and the festival again celebrates Juneteenth a bit early, once again turning the turn-of-the-century Healdsburg Plaza into a full-on outdoor concert venue with a stage set up opposite the gazebo. There will be multiple artists in this six-hour show—including the aptly-billed “the Dynamic Miss Faye Carol” (a contractual obligation), singer Tyreek McDole (this time with his own quintet), the Orrin Evans Trio and host Greg Bridges of KCSM. Expect pop-up dancers, educational workshops and a celebration of Black culture, starting at 2pm.

Naturally, the Plaza is also the setting of the Festival’s annual entry to the city’s summer Tuesday concert series, Melba’s Kitchen on June 17. The all-women’s big band will set up on the gazebo stage like they own it, and for two hours they will.

Bacchus Landing

On the heels of Juneteenth comes Fathers Day, and the first of several shows at Bacchus Landing. Located less than a mile west of Healdsburg off Westside Road (known as Mill Street in town), it’s home to eight well-appointed tasting rooms, an expansive open-air piazza, bocce courts, and more.

OUTDOOR CONCERT Healdsburg Jazz, the single largest beneficiary of Healdsburg Tourism Improvement District awards, has received more than $100,000 over the last three years. This 2023 concert featured Samara Joy at Bacchus Landing.

On Sunday June 15 it hosts none other than Jake Shimabukuro, known as the Jimi Hendrix of the ukulele due to his explorations of rock, blues and jazz through his instrument. His technical skills and full repertoire will be on display in the Bacchus courtyard, for the Sunday show from 7:30-9pm.

Four other performances take place at Bacchus Landing, including the Glide Ensemble, the choir of the San Francisco church that’s long been a beacon of social justice. They appear on Monday, June 16 at Bacchus with two outstanding guest vocalists familiar to HJF audiences, Kenny Washington and Ryan Nicole.

Come the second weekend Bacchus steps up to host shows every night from Thursday to Sunday, June 19-22. Thursday night Healdsburg will welcome back pianist Jason Moran with the Festival’s artistic director Marcus Shelby and his orchestra. They’ll focus on the music of Duke Ellington, riffing off a show they did at SFJazz in the spring.

Friday night finds perhaps the biggest name of the festival this year, multi-Grammy winning vocalist Dianne Reeves. She’ll appear at Bacchus with Brazilian guitarist Romero Lubambo, himself a return talent to Healdsburg for the nth time. The two recently completed their first album of duets since their careers intersected more than a decade ago.

Two more shows at Bacchus Landing end the week, Saturday finding drummer Terri Lyne Carrington with Christie Dashiell reviving “We Insist! The Freedom Now Suite,” released by Max Roach in 1960. Sunday night the traditional New Orleans finale welcomes Big Chief Donald Harrison, with Big Easy trumpeter Nicholas Payton. By then it’s June 22, summer in Healdsburg, and the festival ends with the 9pm encore.

KC Mosso the elephant bar
KC at the bar: KC Mosso serves up a Hamm’s at the Elephant in the Room, Healdsburg, May 2022. (Christian Kallen)

The Elephant in the Room

Second only to Bacchus Landing as a popular venue this year is the Elephant in the Room (117 on Healdsburg Ave.), a friendly pub near the roundabout. No fewer than four festival events are scheduled for this modest pub, known for its craft beers, local wines, tasty bites and wide variety of music offered throughout the year. Though attendance at “the L” is limited to about 90, that makes it an intimate and friendly place to hear any kind of music—and jazz is no exception. (Though the Elephant’s KC Mosso does acknowledge that jazz fans tend to drink more wine than beer.)

Shows at the Elephant are scheduled for later in the evening, after the “main event” of the day. It starts June 13 with the Lorca Hart ‘Bridges’ Quartet with organist Brian Ho starting at 9:30; and continues the next night with saxophonist’s Howard Wiley Quartet, also at 9:30.

Later in the week festival’s Master Artist in Residence Bruce Forman and his trio play the Elephant, on Thursday night. Friday night it’s something completely different – Los Tangueros del Oeste bring several styles of tango to the floor, from classic to Astor Piazzola to today’s “nuevo tango.”

Elsewhere

It wouldn’t be the Healdsburg Jazz Festival without surprises and variety, and that applies to the venues as well. The most far-flung of these is Overshine Winery, two miles from the Plaza (2201 Westside Road). That’s the rural location for a Tuesday, June 17 lunch concert with harpist Destiny Muhammad’s quintet, along with poetry and pizza.

Tiffany Austin
Photo by Leah Marie Studio | INSPIRATION Tiffany Austin never gave up singing on her way to earning a law degree and is now a widely recorded artist, teacher and organizer, as well as music director of the Healdsburg Freedom Jazz Choir.

The Spoonbar at h2Hotel (219 Healdsburg Ave.) will see a cocktail concert on Wednesday night, two shows at 6 and 9pm featuring the Amina Scott Quartet. The young Oakland bassist is the festival’s Rising Star Artist in Residence this year, and she also gives her personal take on jazz on Tuesday at St. Paul’s Church (209 Matheson St.), yet another one-off venue for this year’s festival.

Three other one-off venues include the Healdsburg Community Church (1100 University Ave.), where the Healdsburg Freedom Jazz Choir, led again by Tiffany Austin, performs their annual show on Saturday afternoon, June 21. Late that same night, Hotel Healdsburg’s Spirit Bar (25 Matheson St.) is the scene for a free-flowing jazz jam from 9:30pm into the night, with some of the talent in town for the festival, led by the Sylvia Cuenca Trio (the third female drummer with top billing this year). 

The final day, Sunday June 22, finds young saxophonist Melissa Aldana in an afternoon concert at the tasteful Paul Mahder Gallery (222 Healdsburg Ave.) before the New Orleans finale at Bacchus.

So there it is: 19 musical events spread over ten days, most within walking distance of downtown. Variety, exercise, good wines and great music, since 1999.

For complete information and ticket links, visit www.healdsburgjazz.org

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Christian Kallen has called Healdsburg home for over 30 years. A former travel writer and web producer, he has worked with Microsoft, Yahoo, MSNBC and other media companies. He started reporting locally in 2008, moving from Patch to the Sonoma Index-Tribune to the Kenwood Press before joining the Healdsburg Tribune in 2022.

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