Musicians love coming to Healdsburg in June, when the nights are warm and the days are long. The wine is good, the food is good, the jazz-literate audience is attentive and 10 days of music is just about right.
What about winter? That’s the question the Healdsburg Jazz executive director, Gayle Okumura Sullivan, asked the Healdsburg Jazz board two years ago. The board responded with a tentative “Yes,” and last January found Jason Moran, Edward Simon, Paula West, Sasha Berliner and others sharing their talent with local audiences.
This year the second Healdsburg Winter Jazz Festival, which starts Thursday, Jan. 29, at the Harmon Guest House’s Merritt Hall and concludes Sunday night, Feb. 1, at the Healdsburg Community Church, once again showcases a diverse line-up of talent, genres and venues. A total of six programs are being presented at off-beat stages, with a suitably wide-ranging menu of jazz.
Why a Winter Jazz Festival? When we asked Artistic Director Marcus Shelby last year, he credited the idea to Sullivan, who said she hatched it with Doug Kaminski at Montage. “The idea came from Gayle, our executive director. We had been for years trying to create a year-round concert and programming format,” Shelby said. “It’s taking the opportunity of concert performances and bringing in national and local artists for four days, sort of an action-packed four evenings of music.”
In other words, don’t let the music die.
Tasting rooms
There are several returning artists, a variety of venues and a replay of the “Harlem of the West” concept from last year. Opening night begins with vocalist Gabrielle Cavassa, who introduced her “molasses phrasing and plush velvet tone” to local listeners in the 2024 summer Jazz Festival in an appearance with Jason Moran.
This time she is paired with inventive Los Angeles guitarist Gabe Schnider for the Jan. 29 opener, at the Harmon Guest House’s Merritt Hall. All ticket-holders get a glass of wine from sponsor Overshine Wine. Two shows, at 6pm and 8pm, are on the calendar.
Overshine Wines will also be served at two afternoon concerts at the Idlewild Tasting Room at 132 Matheson St. The first will be on Saturday, Jan. 31, at 2pm. Guitar maestro Mimi Fox and bassist/vocalist virtuoso Jeff Denson form two-thirds of the San Francisco String Trio (with violinist Mads Tolling, who’s playing on the Saturday night lineup), so they speak each other’s musical language.
The other concert at Idlewild is the next day, Sunday Feb. 1, again at 2pm. Clarinetist Ben Goldberg and drummer Scott Amendola explore the possibilities of duo improvisation. As they are both fans of Thelonious Monk, one can expect new angles on improvisation at the afternoon program, starting at 2pm.
Gallery and a church
Once again the Paul Mahder Gallery hosts two key concerts in the Winter Fest. The first is Friday night, Jan. 30, with the Jahari Stampley Trio. Pianist Stampley won the 2023 Herbie Hancock Institute of Jazz International Piano Competition at the age of 24. He’s since been playing with his life-long bassist, his mother, D’Erania Stampley. She brings on electric upright bass, alto sax and synth to back up her piano-playing son. Drummer JongKuk Kim rounds out the trio. One show only, Jan. 30, 7pm at 222 Healdsburg Ave.
The next night, or should we say the next afternoon, the Gallery is the scene of a three-hour “Harlem of the West” Jazz Party, an extravaganza hosted by KCSM DJ Greg Bridges, a long-time supporter of Healdsburg Jazz. The participants plan to not only play with their familiar bandmates, but to share talent across the board for a lively creative celebration.
Vocalist Jackie Ryan; Craig Handy on saxophone; pianists Tamir Hendelman and Tammy Hall; violinist Mads Tolling; bassists Gary Brown, Marcus Shelby and Kanoa Mendenhall; drummers Scott Amendola and Sylvia Cuenca; and poet Enid Pickett will all take part, staking Healdsburg’s claim as being itself the Harlem of the West. The party begins at 6pm and goes until 9pm—possibly later. Note: This will be concert seating, not the informal café style that some events at The 222 are.
If that’s the highlight, it’s not the end. Joel Ross, one of the key talents in the current vibes resurgence in jazz, brings his Good Vibes quintet to town in support of his newly released Gospel Music album. Sticking with the religiosity of the music, the show takes place at the Healdsburg Community Church, backed by bassist Kanoa Mendenhall, Tyler Bullock on piano, Jeremy Dutton on drums and Devin Daniels playing alto saxophone.
The H2Hotel’s Spoonbar is preparing a special “jazzy” dinner menu across the street from the Gallery, to enjoy that night at the restaurant or to go. It’s another example of Healdsburg Jazz reaching out to and including the wider Healdsburg community, in whatever way it can.
When it’s all over, it’s only a little over four months until the 28th Healdsburg Jazz Festival, from June 12-21, 2026.
Full information and ticket links at healdsburgjazz.org.
