Between Thanksgiving weekend and New Year's Eve, most of the holiday music in Healdsburg comes from inside the town. The Healdsburg Chorus, the Healdsburg Community Band, the New Horizons Band of Sonoma County and Healdsburg Jazz each have a December date. Almost all of those dates fall in one room, the Raven Performing Arts Theater at 115 North Street. The Chorus also opens the Plaza tree lighting.
Two of those concerts are free, and the Chorus charges $25. They play in a nonprofit theater whose annual operating income covers only about 60 percent of its annual expenses, according to its director. That gives December in Healdsburg a particular shape. The season is homegrown and inexpensive, the venue depends on fundraising, and many of the season's ticketed events carry a food or toy drive.
The Raven held its third annual gala on March 13, 2026. The Press Democrat reported that more than 200 supporters came and the evening raised over $40,000 for the theater's programs. The paper also quoted Executive Director Tom Brand on why the money matters.
"As with most performing arts facilities, our annual operating income only covers about 60% of our annual expenses; fundraisers like the Gala enable us to continue our mission of serving our community."
Brand told the paper that part of the gala money would pay to install 375 seats from the Raven Film Center, the separate movie house nearby that closed in 2020. SingleThread Farms, the film center's new owner, donated the seats. In other words, the old cinema's seats are moving to the performing arts stage, and the gala is paying for the move.
The 60 percent figure shapes the December calendar. By Brand's account, fundraisers like the gala are what keep the theater serving the community, and that includes hosting free concerts by community groups.
The Raven's season starts before the holidays do. On Saturday, Nov. 14, it screens HISFF 2026 Audience Favorites, the short films that audiences picked at the September 2026 Healdsburg festival. The next night brings Yolotl de Healdsburg. "Yolotl" means "heart" in Nahuatl. On Nov. 21 the theater hosts Simrit, a world music artist whose albums have topped the iTunes World Music charts.
On those same Saturdays, the Healdsburg Farmers' Market books local musicians: Sheridan Malone on Nov. 14, Shivan Luca on Nov. 21 and The StriderFactor on Nov. 28. Bob Culbertson, Diego Jameau and Jacob Philip Benning follow on Dec. 5, 12 and 19. The market's Fall/Holiday Craft Market runs from October through December.
Merry Healdsburg is free and runs from 5 to 9 p.m. on the Plaza at Matheson Street and Healdsburg Avenue. City of Healdsburg Community Services hosts it with the Healdsburg Chamber and Stay Healdsburg. The posted schedule:
The Raven has its own show that night. Mostly Kosher, whose music the theater calls "a global food-fight of Jazz, Latin, Rock, and Folk," plays on Dec. 4, so someone could catch the tree lighting and then walk a few blocks to a concert.
The Chorus that opens the Plaza evening returns eight days later with its own program. According to the Chorus's history, about 20 community members started it in 1987 with founding director Betty Zukov and accompanist Susan Nelson, and the first concert came in 1988. The directors since then:
That makes this Carpenter's first holiday season leading the group. Winter Illuminations plays at the Raven at 3 p.m. on Saturday, Dec. 12, and Sunday, Dec. 13. General admission is $25. Beth Benjamin, who joined in 2024, is the collaborative pianist. The program runs from Vivaldi and Lauridsen to Irving Berlin and John Williams, with traditional carols and a communal sing.
The Healdsburg Community Band and the New Horizons Band have the free afternoons on the Raven calendar. Here is the full set of Raven dates for the local ensembles:
| Date | Ensemble | Time | Admission | Leader |
|---|---|---|---|---|
| Sun., Dec. 6 | Healdsburg Community Band Holiday Concert | 3 p.m., doors 2 p.m. | Free, donations accepted | Matt Wallace, conductor |
| Sat.–Sun., Dec. 12–13 | Healdsburg Chorus, Winter Illuminations | 3 p.m. | $25 general admission | Don Scott Carpenter, choral director |
| Sat., Dec. 19 | Healdsburg Jazz, Harlem Nutcracker Suite with the Marcus Shelby Orchestra | 7 p.m., doors 6 p.m. | $29–$104 including fees | Marcus Shelby, conductor |
| Sun., Dec. 20 | New Horizons Band of Sonoma County | 2 p.m., doors 1 p.m. | Free | Michael Milbrath, musical director |
The Community Band's listing says the band has been playing music together for 44 years, and it calls the December concert annual. The New Horizons Band started in January 1999 with 12 musicians. It now has 80 members, all over the age of 50.
The Raven has one more free date, a staged musical reading of Immanuel on Monday, Dec. 7. It tells the story of a struggling young lawyer who is accidentally nominated to the U.S. Supreme Court.
The ticketed events of the season tend to send part of their value to a local cause or institution.
On Dec. 19, Healdsburg Jazz presents the Marcus Shelby Orchestra in Duke Ellington and Billy Strayhorn's Harlem Nutcracker Suite. Shelby is also the festival's artistic director, and the Raven calls the Healdsburg performance annual. The concert includes a toy drive for local partners.
Earlier, on Saturday, Nov. 28, Dry Creek Vineyard holds its Holiday Celebration + Marketplace from noon to 4 p.m. at 3770 Lambert Bridge Road. Admission is $45 and covers wine tasting, marketplace access and seasonal bites. The event is for ages 21 and over. There is also a canned-food drive for the Healdsburg Food Pantry, and each can donated earns a drawing ticket.
On Sunday, Dec. 6, the Healdsburg Museum and Historical Society runs its Holiday Homes Tour from 11 a.m. to 3 p.m. Five decorated homes are open, all within walking distance of the Museum at 221 Matheson St. Tickets cost $75, or $50 for Museum members, so a membership makes the tour cheaper.
The same weekend has a free indoor option. The Holiday Artisan Market at Appellation Healdsburg, 101 Dovetail Lane, is open 11 a.m. to 5 p.m. on Dec. 5 and 6. Darcy Russell of Feria Urbana curates it.
That weekend gets crowded. On Dec. 6 alone, the homes tour runs until 3 p.m., the artisan market is open until 5 p.m., and the Community Band starts its free concert at the Raven at 3 p.m.
Once the community concerts end, the Raven brings in outside acts. The Christmas Jug Band and Shana Morrison play Dec. 18. On Thursday, Dec. 31, the New Year's Eve show features SF Comedy Competition winners at 8 p.m., with front-row VIP seats at $78. The Community Band's free concert on Dec. 6 accepts donations, and the gala is the kind of fundraiser Brand pointed to for the share of costs that operating income does not cover.
At Ginger Martin + Co., we follow the people and institutions that give Healdsburg its character through the year, the Raven and the ensembles that fill it among them. If you would like to talk about life in Healdsburg over a December afternoon, we would be glad to hear from you. Get In Touch.
1229 Adams St. St. Helena CA 94574
1229 Adams St. St. Helena CA 94574