What's On in Healdsburg

Los Angeles based singer-songwriter and multi-instrumentalist Omar Velasco blends his Jewish-American and Mexican heritage with influences from folk and soul legends. A seasoned performer who has toured with artists like Father John Misty and Jim James, Velasco’s music bridges diverse cultures and eras. Following a turbulent 2022 marked by profound personal loss, new fatherhood, and the dissolution of his band Amo Amo, he found renewal working with a fruit tree care company. This profound connection to nature inspired his deeply personal second LP, Like the Fruit Falls from the Tree (produced by Jonathan Wilson), which reflects on interconnectedness and the redemptive power of art.

Knoxville, TN natives Sally Buice and Molly Rochelson, known as The Montvales, developed their signature harmonies busking in Market Square. Their music is described as the “feral outskirts of country music,” with descriptive, textured songs addressing themes from heartbreak to gentrification and abortion rights. They released their DIY debut album, *Heartbreak Summer Camp*, in 2020, followed by the more polished, full-band *Born Strangers*, produced by Mike Eli LoPinto (Chris Stapleton guitarist, Emily Nenni producer) at Tractor Shed Studio. *Born Strangers* was featured by outlets like Holler and American Songwriter. The duo has shared the stage with artists including James McMurtry and The Local Honeys. In 2025, they signed with Free Dirt Records, releasing the single “Loud and Clear.”

Never Come Down was born from the vibrant if not occasionally overlooked music scene of Portland, Oregon. Much like the city that inspired them, they’re a smart, charming, off-beat amalgam of varied backgrounds and tastes. In today’s paradoxical world where honoring tradition is often pitted against exploration and innovation, the band confidently walks the line between the modern and the tried-and-true. They’ve gained a loyal following and continue to win over audiences everywhere from Reykjavik’s Iceland Airwaves to San Francisco’s acclaimed Hardly Strictly Bluegrass. They’ve gained the attention of industry veterans, and toured in support of notable acts such as Yonder Mountain String Band and The Travelin’ McCourys, among others. Never Come Down’s live performance never disappoints- with showmanship, originality, songwriting and musical prowess far beyond their years.

Enjoy free live music every Thursday upstairs at the Second Story. Doors open at 6PM, music starts at 7PM. No RSVP needed—seating is first come, first served, with entry based on capacity. Maisy Owen, a Nashville native, has been surrounded by music and the art of songcraft just about all her life. Her unique sound, musical truth and stirring vocals inhabit Dark On A Sunny Day, her debut album, set for release by Tompkins Square on May 1, 2026. There’s more to her than crystalline acoustic picking, her darkly poetic songs stand out from the throng. The sparse, melancholic purity of “On My Way Down” and “Letters” and the surging folk-rock of the title track are a testament to her versatility.

Sam Weber is a Portland-based songwriter whose reputation precedes him. If you haven’t seen him in your town on one of his many extended tours, you might have seen his name on marquees beside Bahamas and Feist, or in liner notes as a songwriter on the next Madison Cunningham record. His songcraft is only rivaled by his musicianship, both of which are disciplined enough to stun and feel effortless. He’s well-practiced at his trade, touring solo or with an ensemble domestically and abroad since 2013. His relentless output — now counting seven full length records in his discography — has led to an examination of human existence, eternal in a fragmenting modern world. His latest LP, Shape Confused Cowboy Be You pushes the boundaries of what it means to be a songwriter in the 21st century. He is a Scorpio.