Thursday, Sept. 24
Little Big Easy
The Brooklyn-based, all-female, eight-piece Brass Queens, inspired by the historic brass culture of New Orleans, perform a free SRO show this week. Doors at 6pm, music at 7pm. At Little Saint, 25 North St., littlesainthealdsburg.com.
Friday, Sept. 25
Short Film Festival
Opening night of the annual Healdsburg International Short Film Festival, which runs through the weekend. Most screening blocks are $20, students $10, full-festival passes $100. It takes place at the Raven Theater, 115 North St. See healdsburgfilm.com for details and special events.
The Lone Bellow
Celebrating their sixth studio album, What a Time to be Alive, the Kentucky-based band returns to Healdsburg following the 2025 BloodRoot Ramble. This is a sold-out show, but a wait list is available. Grizfolk opens at 7pm, main event at 8pm at Little Saint, 25 North St., littlesainthealdsburg.com.
Greg Sarris
The controversial, effective Pomo tribal leader has written his second novel, The Last Human Bear, and will talk about it with Jane Ciabattari in the “Indigenous Voices” series at The 222 on Friday. Free for 18 and under, $50 general admission, 7pm at 222 Healdsburg Ave., the222.org.
Saturday, Sept. 26
Saturday Shoppers
Buy fresh local produce, staples, snacks and crafts, and listen to live music. Healdsburg’s signature Farmers Market since 1974. Starts at 8:30am till noon at the Community Pavilion, 3 North St.
Healdsburg Arts Festival
The popular annual showcase of local artists will be held this year not in the Plaza, but close—along Center Street from Plaza to North (including the “Short Film Festival” at the Raven). Street closure, free admission, from 10am to 6pm. It’s held by the Healdsburg Center for the Arts, in collaboration with the City of Healdsburg. For details check out the website at healdsburgcenterforthearts.org/festival-of-the-arts.
Wine Road Gala
The 50th anniversary of the Wine Road will be recognized with an afternoon tasting for up to 150 member wineries at Foppiano, one of the organization’s founding partners. There will be music so wear dancing shoes, and a silent auction will benefit the Redwood Empire Food Bank and The Healdsburg Museum—which is also celebrating its 50th. From 4-7pm, 12707 Old Redwood Highway, $125 at wineroad.com.
Steve Rubardt Trio
Swinging renditions of Monk, Miles and Standards, eclectic originals and a few surprises. Steve Rubardt on the keys, John Donnelly stands up the bass and Bryan Bowman strikes the skins. No cover but limited seating, menu items and drinks from the bar, from 6-9pm in the lobby bar of Hotel Healdsburg, 25 Matheson St.
Sunday, Sept. 27
Filmfest Finale
The final screening block plus the awards ceremony for this year’s Healdsburg International Short Film Festival starts at 5pm, including presentations and Q&A session with jurors and actors Ed Begley Jr. and Jeff Kober. Held at the Raven Theater, 115 North St. raventheater.org
Jazz Generations
Sylvia Cuenca, a much-appreciated jazz drummer in Healdsburg, will be joined by “multi-generational musicians” for this performance featuring original material along with fresh arrangements of the American Songbook and popular Latin and Brazilian standards at 7pm at 222 Healdsburg Ave. Tickets from $35-$85 (free 18 and under) at the222.org.
Monday, Sept. 28
SpeakUP!
A 90-minute “curated multi-generational community storytelling extravaganza” at The 222, during which selected applicants can share their 10-minute stories or presentations with a live audience. The event is to be held every other month on a Monday night until June 7, 2027. Applications at the222.org/productions/speakup.
Tuesday, Sept. 29
Final Tuesday Market
The final Tuesday Healdsburg Farmers Market is this week in the Community Pavilion from 9am to 1pm, but the Saturday Farmers Market continues into December. Shop for local fruit, fresh tomatoes and baked goods, crafts and gifts at the city’s open-air public venue, 3 North St., healdsburgfarmersmarket.org.
Bill’s Birthday
Grammy-winning guitarist Bill Frisell celebrates his 75th birthday with his Harmony Five ensemble in a night of inventive jazz, blending improvisation and composition. Show starts at 7:30pm, tickets $44 to $89, at the Raven, 115 North St., raventheater.org.
Bluegrass Benefit
Join Ketch Secor of Old Crow Medicine Show, with a special appearance by Molly Tuttle, at Little Saint for an 8pm performance benefiting the gun-violence prevention group GIFFORDS. Before the show the film Louder Than Guns will be screened at 6pm at True West Cinemas. Events $45 each, $80 for both at tinyurl.com/mr2uaxwn.
Wednesday, Sept. 30
Screenwriter Series
True West Cinemas concludes its festival featuring movies written by Michael Tolkin, now a Healdsburg resident. This week it’s the finale, The Player (1992), directed by Robert Altman and starring Tim Robbins and Greta Scacchi. Screens at 7pm, 371 Healdsburg Ave. Info and tickets at truewestfilmcenter.org/show/the-player.
For additional events, visit healdsburgtribune.com/calendar.
