Afternoon, babes! What a Saturday. I’m picturing all of you out there basking in this lavish late-spring sunshine, frolicking ’round the hamlet of Healdsburg like it’s your job. And the weather is supposed to get even hotter this coming week, with highs way up there in the upper 80s. Where I come from — here! — we call these RIVER DAYS. So if you see a crazy blonde float by you on the lazy waters of the Russian River one day soon, with a dedicated cooler tube strapped to her ankle, please do wave “Ahoy” to your favorite local newsletterist. You may also catch me at some of the myriad other fun local events on our communal calendar this week, as compiled in today’s log. Here’s what we’re working with:
The third annual Edge Esmeralda “popup village,” full of trippy talks on futuristic topics — some of them free for locals
A full moon yoga session up in Cloverdale tomorrow
Healdsburg’s one-day music festival, headlined by a ’90s legend
A rowdy poker tourney hosted by our local Kiwanis Club
An edgy music improv show just announced at the Raven
And so many more ways to make the most of these sunny days and warm nights in paradise. Scroll down for the goods 🍭
But first! Let’s take a moment to congratulate this year’s dogged softball team from Healdsburg High School. Our girls made it all the way to the North Coast Section’s Division 6 championship game last night, which they played right here on their HHS home field. In the end, the Hounds reportedly lost by 6 runs to one of the toughest teams in the region: Justin-Siena High from Napa. Still, they’ve had quite a season. Their coach, Brian Osborn, tells the Healdsburg Tribune: “I am proud of this team. They put in the work.” And while their counterparts on the boys baseball team didn’t make it quite as far in the playoffs, they too had some flashy highs this season — with four different kids setting school records in runs, hits and pitches. So yeah, hats off!
And next up, our weirdly excellent baseball team in the summertime collegiate leagues, the Healdsburg Prune Packers, will kick off their season this Friday night at Rec Park; you’ll find all the details below in this week’s calendar, naturally. 🧢
Also! A reminder to keep nagging your friends and neighbors about joining us on board The Healdsburg Newsletter, so they too can partake in all the wonderful things going on around here. In the kind words of my seat mate at last night’s TOWN dinner, held deep in a wine cave off Westside Road (a mad tale for another time): “I have more fun in Healdsburg because of your newsletter.” So by all means, send this subscribe link to anyone who comes to mind… or just forward them this email, so they can click the link themselves. Can’t wait to welcome your people into the fold. 🥰
AIR OVER HEALDSBURG

FYI, this is what’s happening over your heads today... (Photo: Holly Wilson)
ON THE CALENDAR
Featured event (from my sponsor!)
“Comedy in the Courtyard” at the Michel-Schlumberger Wine Estate, with sets by standup comedians Cory Loykasek and Lachlan Patterson (Fri, Jun 26, 6pm)

Cory Loykasek of the “Dress Up Gang” comedy troupe, one of Healdsburg’s biggest success stories, returns from L.A. to his hometown every so often to make us all laugh a little — and he loves nothing more than to bring some of his favorite comedians along with him. This time, he’ll introduce us to the great Lachlan Patterson, runner-up on NBC’s “Last Comic Standing“ reality show. “Join us for an unforgettable evening of standup under the summer sky,” say the folks from Michel-Schlumberger, the gorgeous Dry Creek Valley winery hosting the event. Doesn’t get much more Healdsburg glam than this! (Image: Cory Loykasek)
Saturday, May 30
Third annual Edge Esmeralda popup village at Healdsburg hotels and other venues, for “people building a brighter future” (May 30-Jun 27)

Around 1,000 interesting folks from around the world descend on Healdsburg each June for an ideas festival of sorts called Edge Esmeralda. Lead organizers Devon Zuegel and Janine Leger are pictured here speaking to attendees at Seghesio Family Vineyards on Grove Street, for their first-ever festival back in 2024. You can see the full programming calendar here for their 2026 run. Just like last year, Sonoma County locals get 10% off the full ticket price — which still comes out to more than $2.5K for the full month. Or you can get a free ticket for hosting an attendee from out of town at your house, but it might be a little late for that. The other good news, though: Locals can attend all Edge Esmeralda events for free on Wednesdays! Learn more here. (Photo: Edge Esmeralda)
Movie showings this week and next at True West Cinemas: “Tuner,” a new crime thriller with Dustin Hoffman; “Backrooms,” a sci-fi/horror film whose director grew up in Petaluma; “Pressure,” a war drama starring Brendan Frasier that’s getting great reviews; free kids matinee screenings of “The Lego Movie” and more (daily, 11am-11pm)
“Last Days of Spring” wine and art release party at The Harris Gallery: “An evening celebrating new wines, new works, and the vibrant arrival of summer in wine country” (2-5pm)
The Dynamic Duo plays classic rock covers at the Spicy Vines tasting room (3-6pm)
Yours truly bartending at the Dry Creek General Store & Bar: Come say hi! (4-9pm)

Shoutout to all my regulars at Dry Creek Bar, who always keep me honest and entertained! (Photo: Simone Wilson)
Steve Rubardt Trio plays live jazz at Hotel Healdsburg (weekly, 6-9pm)
Jovino Santos Neto Trio plays live jazz at The 222 (7pm)
Country line dancing with live music by Dustin Saylor & The Stowaways at Coyote Sonoma (monthly, 7pm)
Cloverdale Wine Walk hosts “Uncorked: A Prom Night to Remember” party at Trione Vineyard and Winery in Cloverdale (7-10pm)
Steve Pile Band plays rootsy African-inspired music at the Elephant in the Room pub (8pm)
Sunday, May 31 🌝
Upgrade your subscription to keep reading!
Become a premium subscriber for $4-$5 per month to read the rest of The Healdsburg Newsletter.
Join us


