What's Next For This Changing Wine Country Darling Town: The After Hours

HEALDSUBURG, CA — It was a warm night when I drove into Healdsburg past the wineries and vineyards.

Along the plaza, lights shimmered overhead from The Matheson's Roof 106 terrace, while couples wandered about below.

One man — carrying a guitar held to his chest like a present — walked hip-to-hip with a woman, both bashful and still careful to keep an inch between them.

The town has turned into a wine country darling, where the monied part of Healdsburg seeks to stand out quietly with little touches of posh conviviality.

There is the sleek h2hotel, and its signature restaurant Spoonbar, and the velvety Michelin-starred SingleThread farm-restaurant-inn, which just landed at No. 8 on a best restaurant list and is gushed over in every weekend wine country blog I could find.

It only took a few months to fill that list with new must-go places such as Maison Healdsburg wine bar and Bistro Lagniappe, not to mention the places to buy olive oil, honey, coffee, tea, and bread. The boundaries of must-visit places even expanded physically and geographically with celebrity chef Charlie Palmer's Appellation Healdsburg hotel-restaurant complex — where accommodations for the Oct. 3 weekend start at a minimum of $744 a night.

Outlines of Healdsburg's past have been turned into vintage accoutrements — brick storefronts recast as restaurants, weathered signs preserved like artifacts.

I wandered into the Furthermore Wines tasting lounge on Healdsburg Avenue, which was (I was told) once occupied by a bowling alley.

Healdsburg Avenue is the town's main street where, for a couple of blocks, barbershops and shoe stores still mingle with antique shops, design furniture boutiques, and an art gallery. It's also home to John & Zeke's Bar, where one afternoon when it was still the B&B a man drove in and casually parked his Harley Davidson next to the pool table and a three-legged dog that had also wandered in.

Tonight, women in lipstick and cocktail dresses poured out of a chartered limousine bus parked in front the bar.

It was about 10 p.m. and getting late by Healdsburg standards.

With nearly every inch of the bar already filled, I walked on, past a former machine shop that celebrity photographer Annie Liebovitz and family bought then sold. It's still empty, but a dark walkway led to a small courtyard, and then to the Mitchell Shopping Center on Center Street.

Its parking lot was mostly empty, but the lights were still on in the Flakey Cream Do-Nuts and Coffee Shop. Inside, a man was kneading a mound of fluffy donut dough twice the size of a bowling ball while music played in the background. Donuts — glazed, dusted, and sprinkled — lay on trays, still steaming from the oven.

A few doors down, two teens stepped inside the neighboring liquor store and shot straight to a refrigerator stocked with super-charged energy drinks.

The row of storefronts was quiet and several shops have moved out. Across the street, Bravas tapas bar was winding down for the night.

The old Raven Film Center was still dark. Forever, it seems, as a cinema. The owners of the nearby SingleThread and its property management arm acquired the building in 2023.

Around the corner, on North Street, I stepped into the Raven Performing Arts Center. The performance that night hadn't yet ended, and I chatted with a man behind the counter who heard there were plans to turn the movie theater into a sort of international food court for the discerning.

But, he said, the True West Film Center, tucked between two restaurants on Healdsburg Avenue, will be bringing movies back to Healdsburg in October with a block party.

The town felt like the wine industry itself. In one plaza, the restaurants were packed, music spilling onto the sidewalks, visitors laughing over glasses of Chardonnay.

A few streets over, the storefronts were dark, lease signs in the windows, the night quieter, waiting for the next wave of change to arrive.

I caught the scent of Healdsburg in late summer — the sweet, sharp musty smell of wine grapes being harvested.

I couldn’t help but wonder how long the dividing line would hold before new boutiques, bars, and restaurants pushed further out. Where will this journey take Healdsburg?

The After Hours is a recurring column written by Patch Editor Angela Woodall where she will share her opinions on all things that happen after hours. The opinions expressed are her own.