Where to Wine and Dine in Healdsburg, Sonoma County's Coolest Town

A first taste of Healdsburg

To get to Healdsburg, I drive an hour and a half north of San Francisco from the airport. (There’s also a shuttle.) The best and fastest route is straight through the city streets to the Golden Gate Bridge, past Marin County, until I reach Sonoma’s scenic farmland and vineyards.

By dinner, I’m sitting at a long table in Aperture Cellars’ tasting room. The room is a large dome shaped like a camera shutter overlooking rows of gorgeous green vineyards. It’s a Tuesday night, and Aperture owner Jesse Katz has invited me and a dozen of his friends over for dinner. Like most people in town, they work in Healdsburg’s food, wine, and hospitality industries.

Katz, a 39-year-old maverick, is taking Sonoma’s wine industry by storm with his innovative approach to winemaking. He and his friends have created a community of growers and chefs — forging the next generation of Sonoma restaurateurs and winemakers. On the walls of the modern, minimalist tasting room are his dad’s large, stunning photographs depicting scenes from all over the world. As Katz explains it, he first became fascinated with wine at age 12 after his father, photographer Andy Katz, brought him on assignment to take pictures of vineyards on different continents. This was his baptism by fire; it explains how a kid from Colorado became a part of the small, elite world of Sonoma winemaking, and why he’s now slowly changing it from the inside out with his delicious reds and whites.

“There’s a community of people that happen to be in Healdsburg but are affecting the whole wine and food industry,” Katz says. Many of them are around this table.

I meet Kyle and Katina Connaughton, owners of SingleThread, a famous three-Michelin-star restaurant, inn, and farm. The couple, who are chef and head farmer, work hand in hand to create a one-of-a-kind culinary experience that’s highly influenced by their time in Japan. At the farm, they grow their own rice, Japanese vegetables, and flowers in order to create a locally sourced, authentic experience.

There are a handful of Michelin stars among the group seated at this long table overlooking the rows of vines just steps from our table. But for Jesse Katz, this is just another Tuesday night with friends. Dinner is served family-style with platters of sliced roasted lamb, salmon, potatoes, and farro passed from person to person. Chef Jamil Peden comes out at the end to tell us about hunting for our dessert — strawberries fresh from the field. And of course, there’s wine. Lots and lots of wine. It seems all of the guests have brought a bottle, many from their own vineyards, wineries, or collections.

Baron Ziegler brings a bottle of his wine, Marine Layer. The young dad of five girls is the visionary behind the popular tasting room on the square. (I highly recommend it.) So has Dustin Valette, chef and owner of Michelin-starred Valette and The Matheson. Valette calls himself “an avid home winemaker” — which he harvests from his uncle’s vineyard in Alexander Valley just north of Healdsburg — but jokes that he’s a better chef than winemaker who should stick to cooking. Everyone laughs. In fact, Valette is the most down-to-earth, friendly guy you’ll ever meet. Actually, pretty much everyone at the table is.

Sitting across from me are heavy hitters in the local wine community: Phil Freese, a viticulturist, and winemaking legend Zelma Long, an industry icon. But you’d never know it by their easy going, amiable demeanor. Both are Katz’s friends, and Freese has been working with Katz from the beginning. Soon after the food comes out, Katz uncorks a bunch of Aperture wines: classic whites and reds and a few special ones like Devil Proof, a malbec that helped to establish Katz as a “rising star.” He’s been named “40 Under 40 Tastemaker” by Wine Enthusiast and made history as the first winemaker on the Forbes “30 Under 30” list.

I love the hearty, deep, bold taste of the Devil Proof red and also Aperture’s chenin blanc (a light white wine) and sauvignon blanc, which I learn about at their “soil series” tasting the next day. Anyone can visit the estate and vineyard for one of Aperture’s many tastings and events.

Aperture Cellars: 12291 Old Redwood Highway, Healdsburg, California

An innovative approach to Sonoma winemaking

One example of Katz’s out-of-the-box thinking about winemaking is his ideas about what he can produce here in Sonoma. While he says “Napa is king of the cab” (cabernet), Sonoma has traditionally been known for its chardonnay, pinot noir, and zinfandel, which are best suited for this particular soil and sun exposure (or what they call terroir) at the crossroads of the Alexander Valley, Dry Creek, and Russian River.

Katz realized through the process of testing the terroir at Aperture, and his vines at Farrow Ranch and Oliver Ranch in Alexander Valley, that this was also a perfect place for planting grapes to make Bordeaux wines and malbec.

While some criticized Katz’s idea, his experience working in the Bordeaux region of France and with a malbec producer in Argentina helped him prepare for what would be the biggest bet of his life. Today, they are among the highest rated wines. In other words, he bet the house and won. And now this Colorado native is here to stay.

How this community of growers works together

“I lived in Bordeaux, Napa … but this truly feels like home,” Katz says. “Here is a community of people where friendship and family comes first. People come from all over the world to see what we’re doing, and I’m happy to call them my friends.”

In 2022, when a heatwave hit Northern California, with temperatures over 100 degrees, Aperture’s grapes turned to raisins. But Katz knew his misfortune could help his friends.

“I knew pretty quickly the wine wouldn’t be good, so we called Kyle [of SingleThread] and Dustin [of Valette], and they picked up 10-20 pounds of these raisins,” he explained. “Kyle turned it into a syrup that he used on a dessert at dinner at SingleThread and for a sparkling beverage, while Dustin used it to make a mustard dish for his restaurant.”

Touring organic SingleThread Farm for sustainability lovers

On my second day in Healdsburg, I visit Kyle and Katina Connaughton’s SingleThread Farm, which supplies their restaurant and inn with all its vegetables, fruit, herbs, flowers, and honey. Many of these are Japanese varieties that aren’t found elsewhere in the US, giving new meaning to farm-to-table cuisine. Basically, the restaurant can’t exist without the farm.

Sarah Poirier, a friendly, brown-haired woman, greets me with a big smile at the farm shed, offering me a cold bottle of water. At the farm stand, visitors can buy Japanese pottery, fresh greens, and other goodies from the fields. Some of SingleThread’s homemade strawberry jam from last season is available for purchase, along with staples from its kitchen, such as Japanese inspired Chunky La-Yu (a delicious almond garlic chili oil) and homemade ponzu sauces.

Anyone can visit the farm, which also holds classes. We spend about an hour walking through the 24 acres in the hot, blazing, late afternoon sun. I see peas, squash, and varieties of Japanese vegetables and greens I’ve never heard of growing in open-air greenhouses. We come upon row after rows of strawberries, which Sarah tells me to pick and eat off the vine. They are juicy and warm. It’s a treat to eat right from the ground. On the farm, Poirier tells me that they “grow with organic practices and some biodynamic practices as we learn this land.” What’s special about this experience is that the more I learn about the food here, the more inspired I’m to live sustainably.

“If you’re interested in eating in a more healthy way,” Poirier suggests “becom[ing] friends with your local farmers at a farmers market or CSA.” CSA stands for Community Supported Agriculture, a food-distribution model that connects consumers directly with producers. I make a mental note to do that when I’m back home.

SingleThread Farm: 2836 Dry Creek Road, Healdsburg, California

Where to eat and drink in Healdsburg

Black Oak Coffee Roasters

I wake up the next morning and venture out for coffee at Black Oak Coffee Roasters just one block from my B&B, the Healdsburg Inn. It’s exactly what I imagine a coffee shop would look like here in this arty, foodie town. There’s a cool mural on the back wall, and the roastery serves many different kinds of coffee roasts and pastries. I’m in heaven. I order a black coffee with almond milk and try both the gluten-free blueberry scone and a gluten free-sticky bun. Both are still warm. I’m smiling as I eat them, happy there are so many gluten-free and dairy-free options.

Black Oak Coffee Roasters: 324 Center Street, Healdsburg, California

LO & BEHOLD

For lunch, Katz and Aperture’s Hospitality Director Lauryn Mitrovich take me to LO & BEHOLD, which serves “global comfort food” and cocktails. I start with the pea shoot salad with sesame and sunflower seeds, then have the pollo a la brass, blackened chicken thighs in a peppery aji sauce. The food is very fresh on account of all the local farms. Many of the dishes have an Asian or South American influence. The cocktail list is substantial. We order the Tropic Thunder (a Pisco and rum drink) and a mescal concoction called Love Bizarre. Both get high praise.

LO & BEHOLD: 214 Healdsburg Ave., Healdsburg, California

Sushi by Scratch

If you’re looking for a memorable dinner, try Sushi by Scratch. This 17-course omakase sushi meal is an experience. The evening starts outside with an amuse bouche on the patio — a refreshing whisky yuzu cocktail and sashimi in a glass bowl filled with pebbles. I’m soon whisked away through a secret door to a speakeasy where I’m dazzled with 17 separate small plates of sushi and sashimi. The chef uses a blowtorch on a few courses and tells jokes as he spoons out extra ginger for a palette cleanser. The staff are entertaining and inform me about each course throughout the tasting. I loved it, and you will too. This is great for solo diners, couples, and families celebrating a birthday or anniversary.

Sushi by Scratch: 106 Matheson Street, Healdsburg, California

Troubadour Bread and Bistro

My last night in Healdsburg, Katz brings me and a few other people from Aperture Cellars to Troubadour, run by an alum of SingleThread. I loved the inventive dishes, which start with a glass of Champagne before a multi-course prix fixe meal. The small courses come out on small, funky, mismatched antique plates, cups, and saucers. They range from creative takes on croque monsieur, to a decadent danish rye with caviar, to asparagus with ramps. The most spectacular dish is the visually stunning main course — an all white dish of white halibut with white asparagus in a white sauce. I’ve never seen or tasted anything quite like it. If you’re looking for something more traditional, Troubadour also serves a variety of outstanding lunchtime sandwiches that are popular with locals.

Troubadour: 381 Healdsburg Ave., Healdsburg, California

Where to stay in Healdsburg

Healdsburg Inn on the Plaza

This charming inn is centrally located right off the town square in the heart of Healdsburg. From here, walk to any restaurant or shop in town in less than five minutes. The inn has a dozen spacious guest rooms with high ceilings, bay windows, balconies, and large bathrooms with claw-foot tubs and showers. The inn serves breakfast each morning in a small casual dining room and happy hour in the evening. Just let them know your dietary preferences and allergies.

Healdsburg Inn on the Plaza: 112 Matheson St, Healdsburg, CA 95448