Rise and shine, good people of Christmastown! Simone here with your weekly local event guide. I worked on it all night like a manic little North Pole elf, because this morning I need to dash out the door on a cider-rescuing mission at a friend’s orchard in Sebastopol, then dash back for a family tree-chopping mission in the forest behind my house… racing the coy December sun all the while. Tis the season! BTW, I’m also still whittling away at your next news roundup — filled with stories like Cloverdale politicians letting the giant new “Esmeralda” village move forward, a 24-hour gym opening in Healdsburg, Michelin launching a star-like ranking system for wineries and so much more — but in the meantime I don’t want you to miss out on all the events happening in town. To that end, here’s some of what you’ll find on the calendar this week (sung in the style of “The Twelve Days of Christmas,” just ’cause):
Twelve wild new holiday cocktails to try at Spoonbar
Eleven winery stops on a tour of local “gold-medal wines”
Ten artsy workshops for making gifts, decor and treats
Nine days left til the winter solstice celebrations begin
Eight games remaining in the sweaty REIBT b-ball tournament
Seven movies playing at Healdsburg’s shiny new cineplex
Six fun ways to donate toys in town (some involving wine!)
Five different photo ops with Santa Claus
Four festive audio streams converging, with your help, for the “Unsilent Night” caroling parade through Healdsburg
Three classic holiday concerts at the Raven Theater
Two local “posadas” — aka, Mexican Christmas parties
One big candle lighting in the plaza for Hannukah
And tons more cool stuff that doesn’t fit into this schema 🤓
Speaking of Santa! If you happened to stop by the “Merry Healdsburg” extravaganza in the plaza two Fridays ago, and happened to pose for a pic or two with our local Santa Claus, you can root through the city’s photo dump to find your pics here. And below are some magical captures of this year’s event at large…
The fifth annual “Merry Healdsburg” tree-lighting ceremony in the plaza drew the event’s “largest crowd yet,” according to city officials. The lovely man who takes the posed Santa pics, Will Bucquoy, summed up the scene well when he wrote: “If Norman Rockwell were alive today, this is the living canvas he’d capture — a portrait of small-town joy shining bright.” (Photo: City of Healdsburg via Facebook)
As always, the star of the show at “Merry Healdsburg” this year was the inimitable Santa Tim — aka, Windsor resident Tim Oxford, who’s been playing this role for decades now. I’m even starting to think he might be the real thing?? See more pics of Tim living his best life, below — along with a bunch of other great shots that night from one of our community’s most treasured photographers, Tenay Macmillan. (Photo: Tenay Macmillan)
Nuff said. (Photos: Tenay Macmillan)
By the way, I hear Cloverdale’s big downtown holiday event that same evening was pretty wonderful as well, as well as Forestville’s the night after, and Windsor’s the night before. The San Francisco Chronicle is even trying to declare Windsor a top Christmastown too now! It’s not a tough argument to make, what with the hundreds of mini lighted Christmas trees currently surrounding the Windsor Town Green, and the dazzling Wonka-land of a candy shop lighting up the green’s southern stretch. (That shop, Cravin’s Candy Emporium, is actually up for sale right now, according to the Press Democrat — in case any of you have secret dreams to be the future Wonka of Windsor, and can scrounge up $1.5 mill before the next guy.)
Windsor also gets some points for hosting the epic, miles-long Mother Mary procession through town in the wee hours yesterday, in honor of Our Lady of Guadalupe. The PD estimates that around 1,500 devotees marched in the 25th annual edition of this community foot parade. The paper’s mystical parade photos show glimpses of shadowy horsemen in the fog, pilgrims in giant feather headdresses, steaming pots of tamales and all manner of lit-up Mary candles and effigies. Which brings us to the procession’s hood ornament of sorts: a long-lost Guadalupe statue from Mexico City that was reportedly just rescued from some guy’s backyard and restored to glory this year, for the event’s silver anniversary. (Can you tell I’m a little obsessed with Our Lady?) Watch her in action, below. 🖤
A light in the darkness. (Video: Press Democrat via YouTube)
Quick reminder to keep sharing this community resource with anyone who you think could use it. Just send them this link to subscribe! And if they’re extra dear to you, consider giving them the holiday gift of an all-access paid subscription to The Healdsburg Newsletter, by clicking the “Gift” option at the top of this page. You’ll be the proverbial “favorite aunt” forever. 🥰
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Just voted Healdsburg’s best wedding venue
Looks like the Villa’s still got it! Our historic community event space, built along Fitch Mountain’s northwestern slope in 1910 as a country resort for French elite from the city, was just named best local wedding venue in the Healdsburg Tribune’s annual “Best of Healdsburg” reader poll for 2025. This, after the Villa Chanticleer underwent hundreds of thousands of dollars in renovations over the past couple of years, as part of a unique partnership between the City of Healdsburg and the Milestone Events Group. (Every last nook and cranny of the 17-acre, indoor-outdoor Villa grounds have gotten a total glow-up; see pics here.) When the coveted “Best of” award was announced this month, the venue’s new managers wrote in a message to the community: “The Villa has been a place of love, celebration, and connection for generations, and thanks to you, that legacy lives on. We can’t wait to welcome you back and create the next chapter of cherished memories!”
Indeed, the public seems to be taking notice. Weekends in 2026 are getting booked up fast, according to venue managers, with “only a handful of peak-season Saturdays” still available for 2026 — so if you’re eying the Villa as your dream venue, make sure to grab a date before they’re gone. This is the perfect spot to host a big party that still feels cozy and intimate — not just weddings, but also reunions, birthdays, anniversaries, meetings, memorials and other gatherings. And even now that it looks like a million bucks, the Villa is still one of the most affordable options around; you can check out pricing here. Also, keep in mind that Healdsburg residents get an extra 20% off the usual prices! Learn more and book your next event on the Villa Chanticleer website. 🥂
This is what the Villa bar used to look like, way back in the day. (Photo: Healdsburg Museum)
And here it is now! Pretty snazzy. (Photo: Villa Chanticleer)
NOW, AIR OVER HEALDSBURG
It’s been another week full of dense fog that barely burns off by the time the sun starts to set in the mid-afternoon. And again, here’s what the stubborn fog pack over your head looks like this morning. Hang in there, townies! (Photo: Holly Wilson)
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