So you want to live it up like a local in Healdsburg, CA. Can’t say we blame you. As you may have heard: California knows how to party. That’s certainly true in the heart of Sonoma County, where you’ll be welcomed with a culturally vibrant yet walkable downtown, generational family businesses, world-class restaurants and wineries, plus more outdoor adventures than you can pursue in a single weekend. That’s why we’ve saved you some time and pared it down to the essentials.
Fortunately, no matter what season you choose to book your trip, the following events will keep you entertained throughout the year. And these festivities combined with our perpetually divine climate? Well, spoiler alert: it’s always a good time to visit.
Winter
The winter doldrums? Never heard of ‘em. When it comes to these activities, you won’t have cold feet—either in the literal or metaphorical sense.
A Season to Sparkle – November – December
When the days get shorter, everything gets brighter in Healdsburg. Come visit during this series of holiday-themed events, special menu items, and discount packages. Featuring a kickoff soirée, holiday markets, the Merry Healdsburg tree lighting—even quality time with the big guy known as St. Nick—see firsthand why sparkling is our specialty.
Healdsburg Winter Jazz Festival – Last Week of January
Bebop your way to four days of concerts with celebrated artists in cozy venues around Healdsburg, including Montage Healdsburg, Bacchus Landing, and more. There’s a reason SF Chronicle calls it “one of the best small jazz festivals in the country, if not the world.” The rest of your trip might be improvisational, but secure these tickets in advance.
The 222 Winter Performance Series – January – March
Hosting events that center around dance, film, literature, music, cultural traditions, workshops, open mic nights, and community experiences, this beloved venue celebrates craft in all its forms. Immerse yourself in entertainment through an organization that’s committed to embracing innovation and strengthening the connection between artists and audiences.
Spring
You can truly spring forward in Healdsburg. The calendar is in full bloom thanks to this array of activities fit for sommeliers, families, artists, and tree-huggers alike.
St. Patrick’s Day Festivities – March 17
Join our local characters for a march down Healdsburg Avenue in the St. Patrick’s Day Parade, known as the “biggest, shortest parade in the world.” Then start your own set of shenanigans at St. Patrick’s Day on the Plaza for an afternoon of live music, Irish step dancing, and crafts for kids.
Earth Day Climate Fest – April
Learning how to nurture nature and protect our planet has never looked so fun. Find an assortment of booths, live music, eco-friendly demonstrations, and children’s activities like face-painting and crafts, plus food vendors and giveaways.
Passport to Dry Creek Valley – Last Weekend in April
For over twenty years, and highlighting the region’s 140+ year history of winemaking, Passport to Dry Creek Valley partners with local wineries to produce a weekend of gourmet excursions. Rub elbows with the winemakers, grape growers, vineyard owners, and award-winning chefs that make Healdsburg a destination for gourmands the world over.
True West Film Festival – May
Over a decade strong, this ten-day film festival showcases diverse auteurs and avant-garde films from all across the globe. Film buffs can gather, watch, and learn from visiting artists and underrepresented communities. The festival also hosts a student film competition. And stay tuned for the opening of the True West Film Center.
Healdsburg Wine & Food Experience – Third Weekend in May
A weekend-long celebration of Sonoma County’s internationally recognized provisions awaits. Here’s your chance to champion culinary diversity and sustainable farming practices alongside celebrity chefs and winemakers. There’s a full slate of robust events, including deliciously enlightening wine seminars.
Summer
Whether your summer schedule translates to a break from school and work or it’s the same old routine as the rest of the year, your dog days can feel like a true escape when you spend time on this side of Sonoma County.
Healdsburg Jazz Juneteenth Celebration – June 19
Come for the famed jazz jubilee at the Healdsburg Plaza; stay for the historic and culturally enriching performances, workshops, and libations. This event is free to the public, with activities fit for all ages and backgrounds.
Healdsburg Arts Festival – July
Stroll through over 40 booths of artwork in the Plaza. Browse the finest ceramics, woodwork, jewelry, printmaking, photography, painting, textiles, glass, and more. Sip wine, hear live music, and enter a drawing for your chance to win free artwork.
Songwriters in Paradise – July
Revel in four nights of acoustics at four notable wineries. Because plucked strings and glasses of pinot are always better en plein air—especially with the scenic vistas of Healdsburg surrounding you. Select VIP packages for a next-level experience.
Fourth of July Kids’ Parade & Duck Dash – July
Here’s an occasion where kids (and adults) are free to be kids. For the parade, children are encouraged to dress in costume and arrive on bikes, tricycles, or wagons adorned in patriotic regalia. Then, thanks to the Rotary Club, your family can adopt a duck and watch it race to the finish.
Fall
The months ending in “ber” aren’t just for pumpkin spice latte fanatics anymore. In a city that hosts a grape-stomping, howling good time at every turn, you’ll be delighting in sweater weather wherever you roam.
Art After Dark – September
There’s no need to be spooked by this twilit community-wide street fair. From exhibitions to hands-on crafts, each year offers new and exciting opportunities to acquaint yourself with art. Make sure to peep the glorious display of classic cars while you’re at it.
Access Alexander Valley – September
Alexander Valley Winegrowers presents a poolside evening at Francis Ford Coppola Winery with unforgettable vintages and large formats, plus hearty fare from local favorites. Once you’re satiated, you can dance to live music until your partner drags you home.
Howl-O-Ween Pet Parade – October
Bring your costumed pet and circle the Plaza before queuing up at the gazebo for an awards ceremony. This recent tradition is sponsored by the Human Society of Sonoma County, so participate for a good cause and reap the benefits of games, coffee, prizes, and raffles.
Healdsburg Crush – October
Picture tasting booths filled with limited-production chardonnay, pinot noir, and sparkling wines. A silent auction and raffle tickets promising prizes tailored to true connoisseurs. But the biggest perk of all is that 100% of the proceeds benefit Boys & Girls Clubs of Sonoma-Marin.
Dia De Muertos – October – November
Co-sponsored by the City of Healdsburg and Corazón Healdsburg, you can share a memento at the community altar while enjoying Aztec dance and folkloric performances, the car show, and family-friendly activities that unite our community through culture.
You don’t need an excuse to cut loose when you’re staying in Healdsburg, but this curated list should do the trick. Every day is cause for celebration at our Michelin-rated restaurants and wellness retreat options. Regardless, you’ve come to the right place for relaxation. After all, “heal” is in our name.
