In 2020, in the middle of the COVID pandemic, Jessica Felix, the founder of the Healdsburg Jazz Festival, retired. Needless to say, it was a very challenging time for the festival.
Two members of the Festival's Board of Directors, Bay Area bassist, composer, and performer Marcus Shelby became the artistic director, and Healdsburg resident and local business owner Gayle Okumura Sullivan became executive director. Six years later, Healdsburg Jazz is celebrating its 28th year and thriving.
From the very beginning, in 1999, Felix brought in jazz legends, and was also dedicated to being part of and giving back to the local community. Since taking over, both Shelby and Sullivan have expanded that mission.
Shelby has been a driving force in the Bay Area music scene for many years, with a strong focus on African American culture and social justice. He has brought the Festival’s Black History Month programming to local schools, co-founded the Healdsburg Freedom Jazz Choir, now in its 13th year, led by singer and composer and arranger Tiffany Austin, and performed with his own Marcus Shelby Orchestra.
"One of the first things that I did when I became director was I moved the Festival up two weeks so that it would time with Juneteenth and Father's Day, giving us two really strong days to celebrate with music and cultural events, and that has proven to be a solid move."
Originally just four days, the Festival now runs 10 days. In addition, an annual winter festival was added last year, with great success.
"I am pretty much a classical, Black music artist, but when I became director I realized I wanted to expand what we could offer. Our goal has always been to be as diverse as possible when it comes to the programming, so that it represents the full flavor of the artists that are doing great things," Shelby explained.
The musician said that booking the then up-and-coming vocalist Samara Joy in 2024 was a game changer for the festival’s audience. Also in 2025, Hawaiian ukulele virtuoso Jake Shimabukuro made a big splash. ,
The lineup for the upcoming Festival, running from June 12–21, includes prominent headliners such as saxophonist Branford Marsalis; saxophonist Charles Lloyd (with his quartet, including pianist Gerald Clayton); vocalist Kurt Elling (performing with the Marcus Shelby Orchestra); vocalist Lisa Fischer; pianist Orrin Evans; and vocalist Cécile McLorin Salvant.
There will also be many well-established, straight-ahead artists, such as bassist Rufus Reid, drummer Billy Hart, and pianist George Cables, along with Brazilian mandolin player Hamilton de Holanda, and Trinidad-born trumpeter and percussionist Etienne Charles.
Sullivan, who is also deeply committed to enhancing and expanding the Festival, has experience in the tech industry and in marketing, including for Alonzo King LINES Ballet in San Francisco. Always a jazz aficionado, she became interested in the festival after moving to Healdsburg to run a small organic peach farm, Dry Creek Peach and Produce.
"One of the first individuals I met was Jessica Felix," said Sullivan. "And when my son started drumming, he asked Jessica who he could learn from, and he actually learned on her drum kit in her living room. So from that moment on, I got involved with the Festival."
Shelby and Sullivan have both worked to create partnerships with local wineries, churches, the Healdsburg Chamber of Commerce, and a number of Healdsburg businesses. In this way, its budget has grown but the festival also is able to support the local community.
"We're in Healdsburg, Sonoma County, and we are the biggest festival up there, and we have a responsibility as we raise money and do these festivals, to funnel some of that back as far as support to our local community," Shelby said.
The festival’s free educational programs reach more than 7,000 students each year, including family matinees, a music and performing arts camp, after-school jazz, and Black History Month programming.
"Healdsburg is really a beautiful wine country destination," said Sullivan. "I love and appreciate the other big jazz festivals, but ours is very different because all of our concerts are held in really intimate settings. Our biggest venue is maybe 500-600 [seats]. And we are all over town, at 11 locations, and every one is different — primarily outdoors, and truly beautiful. It's a whole different kind of experience."
Both Shelby and Sullivan are optimistic about the future. Shelby wants to continue to expand, but in a very specific way.
“We're not trying to become bigger and bigger," he said. "I think what we are trying to do is become stronger — expanding our education and community outreach, being a factor in our community, and continuing to be supportive of our local artists."
