May has plenty going on. We pulled together some of the events that caught our attention. Wine, music, culture, community, a little bit of everything that makes this time of year worth paying attention to. For more details on each experience, click the event titles.
The Standouts
☀️ May 2nd | Garagiste Festival Sonoma, Sonoma
A focused tasting experience built around small-production winemakers. Less about big names, more about discovery.
☀️ May 17th | Call of the Wild Festival | Jack London State Historic Park, Glen Ellen
Set within one of the valley's most storied landscapes, this festival weaves together storytelling, nature, and creative programming rooted in Jack London's legacy.
Worth Building an Evening Around
☀️ Sonoma Tuesday Night Market | Sonoma Plaza
A seasonal return that reliably draws a crowd. Local vendors, prepared food, and live music centered around the plaza. Take a stroll, grab a bite, or picnic on the lawn.
☀️ Every Wednesday | Acoustic Sunsets | Sonoma Botanical Garden, Glen Ellen
Evening acoustic performances tucked inside the garden. The setting does as much work as the music.
☀️ May 29th | Fairmont Sonoma Summer Music Series, Sonoma
A recurring live music series that runs through the summer, with a rotating lineup of performers in a relaxed resort setting. Good for an unplanned evening out.
For Wine-Focused Plans
☀️ May 3rd | Brunch & Blush | St. Francis Winery, Kenwood
A structured brunch and wine pairing that leans into seasonal ingredients and estate wines. A good option if you're looking to make a morning of it.
☀️ May 16th | Western Reserve | B.R. Cohn Winery, Glen Ellen
A more curated look at reserve wines, typically accompanied by small bites. Worth it if you want something beyond the standard tasting room experience.
Something a Little Different
☀️ May 2nd | Sonoma Valley Authors Festival: Authors on the Plaza
An outdoor extension of the larger festival, bringing author talks and book signings into an open format on the plaza.
☀️ May 21st | Third Thursdays at Sonoma Golf Studio, Sonoma
A low-key mix of golf, conversation, and light bites. A good reason to get out mid-week.
Worth the Short Drive
☀️ May 2nd | 2nd Annual Bloody Mary Challenge | Hotel La Rose, Santa Rosa
You’ll sip, sample, and vote your way through a lineup of uniquely crafted Bloody Mary’s, each with its own twist, while supporting the firefighters who keep our community safe.
☀️ May 14 – 17 | Healdsburg Wine & Food Experience
Multi-day programming featuring chefs, winemakers, and curated tastings spread across Healdsburg.
☀️ May 17th | Sonoma County Matsuri Festival, Santa Rosa
A vibrant cultural event featuring traditional Japanese performances, food, and arts. Held outside the valley but well attended across the region.
Whether something's been on your radar for a while or you decide on a whim, this is when the calendar really starts to take shape. If spending more time in the valley has been on your mind, weekends, or something longer term, our agents know this area well. Reach out to explore Sonoma Valley homes or just learn more about what life in Sonoma actually looks like.
This post was created with the assistance of artificial intelligence and reviewed by the team at Coldwell Banker Brokers of the Valley. Event details, pricing, and availability are subject to change.
We recommend confirming directly with each venue before making reservations.
