DANCERS Members of a Mexican dance troupe enliven the celebration of Dia de Muetos in the Healdsburg PLaza, and annual and popular event. (Photo by Rick Tang)

Best Way to Explore Local Arts Without a Glass

Healdsburg didn’t rise to the top of visitor destinations based on food and wine alone (though it  helped). There’s also a thriving and growing arts scene—in the broadest sense of the word. After all, is Best Trivia Contest really arts, or culture? Or is it just entertainment, more so for the winners than the losers?

And what about Best Place for a Date? Arts? Entertainment? Culture? Or a tantalizing “all of the above”?

Other categories make more intuitive sense, such as Best Live Music Venue, Best Art Gallery and, since this is Healdsburg, Best Live Jazz Music Venue. In these winners we find living examples of DEI (Diversity, Equity and Inclusion), with Mexican culture making a prominent showing through the explosively popular Dia de Muertos in the Plaza, an annual event which has just passed.

The “fine arts” are here as well, represented on the cover of this booklet. The inviting image was taken by Cynthia Glassell, voted Best Photographer in our selection. (The chef of course is Doug Keane of Cyrus, Healdsburg’s first Michelin-starred restaurant—though he has since moved his destination culinary adventure to Geyserville, thus putting himself out of contention for Best Healdsburg Restaurant this year.)

Then there’s Jake Messing’s selection as Best Artist, whose dense and powerful images seem to peer into the oneiric heart of Healdsburg, that dream state between what we think we know and what we can barely imagine.

From the Farmers’ Market to Yoga on Center, horseback riding at Chalk Hill Ranch or watching the Prune Packers play at Rec Park, the winners scratch the surface of Healdsburg’s Arts and Entertainment scale. Fact is, for all the Michelin stars or 98-point wines, chefs or sommeliers, it’s the vitality of life in Healdsburg that draws people here from all 50 states—and keeps them here for a lifetime.

— Christian Kallen


Best Adventure Tour

River’s Edge Kayak & Canoe

Best Art Event

Art After Dark

Best Art Gallery

Paul Mahder Gallery

Best Art Lessons

Healdsburg Center for the Arts

Best Artist

Jake Messing

Best Day Trip

Hike Fitch Mountain

Best Horseback Riding Instruction

Chalk Hill Ranch

Best Latino Community Event

Día de Muertos Healdsburg

Best Live Jazz Music venue

Bacchus Landing

Best Live Music Venue

Elephant in the Room

Best Local Band

Rainbow Jazz Collective

Best Musician

Steve Pile

Best Outdoor Event

Healdsburg Farmers’ Market

Best Park or Open Space

Healdsburg Plaza

Best Photographer

Cynthia Glassell

Best Place for a Date

The Madrona

Best Place to Take a Class

Yoga on Center

Best Plaza Event

Tuesdays in the Plaza

Best Regional Casino or Card Room

Graton Resort & Casino

Best Spectator Sport

Healdsburg Prune Packers

Best Swimming Pool

Parkpoint Health Club, Healdsburg

Best Trivia Contest

Fogbelt Brewing Company

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