Healdsburg’s popular Art Nite brings the downtown gallery scene to life on the first Thursday of the month. Wander from gallery to gallery, meet local artists, browse original works, and enjoy the warm, walkable atmosphere of the Plaza district. A great low-key evening for art lovers.

Tacos Y Vino returns for its recurring Thursday social — a relaxed, delicious pairing of street-style tacos and local wines. A fan favorite among locals for unwinding mid-week with good food and good company in a convivial setting.

A delightful self-guided wine and cheese trail through the scenic Alexander Valley corridor along Hwy 128. Participating wineries invite guests for curated wine, cheese, and charcuterie pairings amid stunning spring vineyard scenery. A perfect way to explore Alexander Valley’s acclaimed producers.

One of Sonoma County’s most beloved traditions returns for the 2026 season. The Healdsburg Certified Farmers Market, operating since 1978, fills the West Plaza parking lot with local produce, flowers, fresh eggs, artisan breads, cheeses, olive oil, and handmade crafts. Runs every Saturday through December 20, rain or shine. Arrive early for the best selection and often live music.

Wake up among the vines with Jordan’s spring yoga experience at the estate’s highest hilltop, Vista Point. Enjoy sweeping panoramic views of multiple wine regions during a 40-minute flow led by local instructor Kelliann Reginato, followed by a locally sourced breakfast with Jordan wines. Also available April 26. Reservations required — advance booking recommended.

Kick off Passport Weekend with a bang at Bacchus Landing. Chef Kevin O’Connor (of Hulu’s Chefs vs. Wild) returns for year two with dramatic open-fire cooking, while DJ Saint Rose Disco keeps the energy high all evening. More than 20 Dry Creek Valley wineries will be pouring. Dress in denim-on-denim for the festive theme. A ticket to this event does not require a full Passport weekend pass.

Boys & Girls Clubs of Sonoma-Marin hosts its elegant annual dinner and auction at the historic Villa Chanticleer, celebrating 22 years of community support and nearly eight decades of service to Healdsburg youth. Enjoy a world-class culinary experience by Troubadour Bread & Bistro, exquisite local wines, live and silent auctions, and youth performances. All proceeds support after-school programs for over 400 local children. Adult event; tickets available at bgcsonoma-marin.org.

Celebrate Earth Week with a guided Sonoma hiking excursion through Jordan’s stunning 1,200-acre estate — featuring mountain views, vineyards, wildlife, and pollinator sanctuaries. The adventure concludes with a wine pairing lunch by Executive Chef Jesse Mallgren. Yoga at Vista Point experiences are also offered April 26. Reservations required.

The biggest wine weekend of Healdsburg’s spring calendar. Passport to Dry Creek Valley lets you travel freely through 50+ wineries spread across 16 beautiful miles, meeting founders, winemakers, and multi-generational farming families. Taste 30+ grape varieties, enjoy celebrity chef bites, live music, and DJ beats. Single-day and full weekend passes available; a non-drinker ticket option is offered as well. A portion of proceeds benefits the Dry Creek Valley Scholarship fund.