Healdsburg Jazz Winter Fest 2026

Sonoma County’s premier jazz presenter Healdsburg Jazz announces the second annual Healdsburg Jazz Winter Fest, a four-day counterpart to its famed summer festival, taking place January 29 – February 1, 2026 in the heart of Northern California’s wine country. Where the rolling hills of the Sonoma Coast meet one of America’s most respected jazz institutions, the 2026 Healdsburg Winter Jazz Fest offers a rare chance to experience today’s buzziest jazz artists up close, surrounded by top-flight wineries, intimate culinary experiences, and Healdsburg’s walkable, picture-perfect downtown.

Under the artistic direction of lauded composer/bassist Marcus Shelby, Healdsburg Jazz continues its mission of honoring the lineage of jazz while championing the next generation of innovators. This winter’s lineup features artists who are redefining modern jazz — Joel Ross Good Vibes, vocalist Gabrielle Cavassa, pianist Jahari Stampley, guitar great Mimi Fox with bassist Jeff Denson, improvising luminaries Ben Goldberg & Scott Amendola, and a deep cast at the Harlem of the West Jazz Party — all presented in cozy, high-touch venues where every seat feels close to the music.

From wine-soaked matinees at Idlewild’s tasting room to a ringing finale at the Raven Performing Arts Theater, Healdsburg Jazz Winter Fest 2026 is designed as a not-to-be-missed destination festival: a long weekend of world-class music, winter vineyard vistas, and the culinary and wine excellence that make Healdsburg a global hot spot.

“I’m honored and grateful to announce the artists for our 2026 Winter Festival, which runs Jan 29-Feb 1, 2026 in some of our most beautiful, intimate venues in Healdsburg, CA, including our historic Raven Theater,” says Marcus Shelby, Artistic Director, Healdsburg Jazz Festival. “We have a really wonderful line-up of national, regional, and local artists performing such as vibraphonist and composer Joel Ross headlining our 4-day festival with his internationally celebrated group ‘Good Vibes.’ Our 2nd annual ‘Harlem of the West’ jazz party promises to be electrifying with a non-stop musical showcase featuring nearly a dozen artists from NYC, LA, and SF Bay Area. We’re thankful to our partnering venues where you will enjoy the music, wine and dine, and meet wonderful people. Much love to our sponsors, donors, and members for the support that makes our winter festival possible. Power to the community. Last year we sold out, so get your tickets today!”

Tickets: $100 / $75 / $55 (includes a glass of wine)

227 Healdsburg Ave, Healdsburg

The festival opens with an exclusive, double-set evening from two of jazz’s most intriguing young trailblazers. With her molasses phrasing and plush velvet tone, Gabrielle Cavassa has quickly become one of the most talked-about voices in jazz. After winning the 2021 Sarah Vaughan International Jazz Vocal Competition, she was tapped by saxophone star Joshua Redman for his acclaimed Blue Note album Where Are We, and her 2024 Healdsburg appearance with Redman left audiences wanting more. Now preparing her Blue Note debut as a leader, New Orleans-based Cavassa returns to Healdsburg on her own terms.

Joining her is Los Angeles Gabe Schnider, a restless and inventive stylist whose harmonic and melodic imagination make him a thrilling guitarist. Together, Cavassa and Schnider treat every tune like a new canvas, diving into the lustrous unknown — a perfect fit for a festival devoted to the evolution of jazz.

Each ticket includes a glass of Overshine wine, connecting the sensuous palette of their sound with the region’s remarkable terroir.

Tickets: $100 / $75 / $55 / $25

222 Healdsburg Ave, Healdsburg

Family bands are nothing new in jazz — but there has never been a group quite like the Jahari Stampley Family Trio. An electrifying pianist and keyboardist, Jahari Stampley exploded onto the global scene with his 2023 win at the Herbie Hancock Institute of Jazz International Piano Competition and has since become a beacon for the future of the music. Check out his just published interview with music legend Rick Beato on YouTube.com.

Stampley’s extended, suite-like compositions unfurl like cinematic journeys, rich in texture and bursting with rhythm. His trio features the dynamo drummer JongKuk Kim and his mother, the revered GRAMMY-nominated artist D’Erania Stampley, on electric upright bass, alto sax, and synth. Their interplay radiates the energy of a fiercely creative household — where the lines between family, mentorship, and collaboration blur into something wholly new.

Tickets: $65 (includes a glass of wine)

132 Plaza Street, Healdsburg

For an afternoon steeped equally in old-school swing and modern lyricism, the duo of guitar titan Mimi Fox and bass virtuoso Jeff Denson brings world-class artistry into the intimate setting of Idlewild’s downtown tasting room. Fox and Denson — two-thirds of the all-star San Francisco String Trio — have long been admired for their ability to reinvent classic material, from the Beatles to Great American Songbook staples, with wit, warmth, and daring improvisation.

Recognized for decades as one of the most formidable guitarists in jazz, Mimi Fox has worked alongside giants such as Charlie Byrd, Stanley Jordan, and Charlie Hunter. Jeff Denson, whose trio Minsarah became the first touring band of alto legend Lee Konitz, is equally known for his singing bass tone and bold compositional voice. Together, they embody jazz as conversational art, trading lines that shimmer with soul-bearing emotion — perfectly complemented by a glass of Sonoma Coast wine in hand.

Tickets: $100 / $75 / $55 / $25

Healdsburg Jazz kicks off Black History Month with a grand, three-hour, non-stop Jazz Party honoring San Francisco’s historic Fillmore District, once known as the Harlem of the West for its late-night jazz clubs and legendary performances. Hosted by KSCM DJ Greg Bridges, this multi-faceted celebration blends music, poetry, photography, and art, extending the jazz tradition from Harlem to the Bay and into the present moment.

The all-star cast includes:

-Saxophone: Craig Handy

-Vocals: Jackie Ryan

-Piano: Tamir Hendleman & Tammy Hall

-Bass: Kanoa Mendenhall, Gary Brown & Marcus Shelby

-Drums: Sylvia Cuenca & Scott Amendola

-Violin: Mads Tolling

-Poet: Enid Pickett

-MC: Greg Bridges

The neighbors at Spoonbar (across from the gallery) will offer a special Jazz Menu for dine-in or to go, letting guests pair an immersive, historically grounded jazz experience with creative cuisine and local wines — a snapshot of why Healdsburg is one of the most coveted small-town destinations in the country.

Tickets: $65 (includes a glass of wine)

There are jazz duos — and then there is the alchemical pairing of clarinetist Ben Goldberg and drummer Scott Amendola, two of the Bay Area’s most celebrated improvisers. For decades, both artists have thrived in stripped-down formats; together, they create a sound that is deeply swinging, and fiercely exploratory.

Goldberg’s duo discography includes acclaimed recordings with Myra Melford, Kirk Knuffke, and Marty Ehrlich. Amendola, whose resume includes landmark projects with Charlie Hunter, Wil Blades, and Phillip Greenlief, may be jazz’s preeminent duo drummer. Their shared history — spanning albums like the Thelonious Monk project Plays Monk and the bridge-inspired suite Here to There — promises surprises, Monk-ian mischief, and fearless improvisation.

Presented in the intimate chamber of Idlewild’s tasting room, and paired with world-class wine, this concert epitomizes the festival’s ethos: incredible jazz, up close, in one of the world’s great wine regions.

Tickets: $100 / $75 / $55 / $25

115 North Street, Healdsburg

The jazz world is in the midst of a vibraphone renaissance, and its brightest star is Joel Ross. Since earning attention in Marquis Hill’s Blacktet, Ross has led the charge for a new generation of vibraphonists, releasing a string of critically acclaimed albums on Blue Note beginning with his lauded 2019 debut KingMaker (winner of the 2020 Jazz International Edison Award).

Ross’s music is at once luxuriantly lyrical and rhythmically daring, as heard on his 2022 suite The Parable of the Poet. His band, Good Vibes, is a nucleus of jazz’s most exciting young players, featuring Kanoa Mendenhall on bass, Jeremy Corren on piano, and Jeremy Dutton on drums. Together, they create a sound that feels like a direct line from Milt Jackson, Bobby Hutcherson, and Steve Nelson to the current moment.

Closing the festival at the Raven, Ross and Good Vibes send the Winter Festival out on a joyously ringing tone, underlining the core message of Healdsburg Jazz: the tradition is alive, evolving, and in very good hands.

“[a] bright young vibraphonist on his own rocketlike trajectory.” — The New York Times, Nate Chinen

“Joel Ross is already widely known as contemporary jazz’s top prospect. KingMaker shows that he has what it takes to build something vital.” — The New York Times (year-end list)

“The bright future stretching before Ross has as much to do with that emotional expression as anything that happens between his mallets.” — NPR

“The 23-year-old vibraphonist shines on his debut album, with an approach that feels sly and mysterious; he also proves himself a sharp bandleader.” — Pitchfork

Lead Sponsor: Overshine. Official Sponsors: Healdsburg Chamber/Stay Healdsburg, Harmon Guest House, Chamber Music America

When: January 29 – February 1, 2026

Where: Downtown Healdsburg, Calif.

Tickets & Info: www.healdsburgjazz.org

The Healdsburg Jazz Festival is a celebration of the indigenous American art form known as jazz. Over the past 28 years, the festival has become a beloved local tradition with a growing national and international reputation. The summer festival — now a 10-day centerpiece of the North Bay arts calendar — presents world-renowned musicians in diverse settings including Bacchus Landing, Overshine Wine, Foley Family Community Center, Raven Performing Arts Theater, Healdsburg Plaza, Hotel Healdsburg, h2hotel, Paul Mahder Gallery, historic theaters, clubs, and other distinctive spaces around town.

In addition to its annual June festival and the expanding Winter Festival, the non-profit 501(c)(3) organization sponsors music education programs in Healdsburg-area schools and presents a year-round Jazz Masters series, reaffirming its deep commitment to community, culture, and the ongoing story of jazz