Where Healdsburg’s Chefs and Winemakers Eat, Drink, and Unwind

10 Minute read

12 Oct 2026

Aperture Vineyards. Credit: Rachid Dahnoun

Kyle Connaughton, Jesse Katz, Robert Young II, and Sergio Howland share their favorite restaurants, tasting rooms, and places to explore in Healdsburg and beyond.

Wine country has long drawn food lovers with its agricultural riches and celebrated wines. In the Sonoma County town of Healdsburg, chefs and winemakers have plenty to savor on their own doorstep, from ambitious restaurants to neighborhood favorites.

For Kyle Connaughton, chef and co-owner of the three-Michelin-starred SingleThread, the surrounding countryside is part of the appeal. “For us I think it’s the mix of agriculture, great winemaking, and wide-open spaces that make this area so special.”

Robert Young II is another champion of the region. An Alexander Valley native, he is a fifth-generation member of the family behind Robert Young Estate Winery, where he serves as sales and marketing manager. “You can visit a winery and meet the owner or winemaker, go to a restaurant and meet the chef, or see families working the same land they’ve cared for, for generations,” he says.

Jesse Katz, founder and winemaker of Aperture Cellars, has seen that community grow, pointing to “the incredible concentration of talent that has come to Healdsburg across the hospitality, culinary, and wine industries.”

Together with Sergio Howland, executive chef at Montage Healdsburg, they share their favorite places to eat, drink, and unwind in town and beyond.

Where to Caffeinate and Eat

Morning coffee takes Howland to Black Oak Coffee Roasters. “Their Ethiopian and Costa Rican coffees are delicious. I’m pretty boring with my order, though: a double espresso with an equal amount of hot water. No cream, no sugar, no sweeteners. Just straight-up coffee.”

Katz agrees on Black Oak and adds Flying Goat Coffee to the list. “Both have brilliant coffee and wonderful atmospheres. I’m usually an oat-milk cappuccino or iced coffee kind of guy,” he says.

Connaughton’s picks have a SingleThread connection: “Definitely the daytime menu at Troubadour and the sandwiches made from their bread at Quail and Condor.” Both businesses are run by his former colleagues, Sean McGaughey and Melissa Yanc.

Howland favors Bravas Bar de Tapas. “The paella and tapas are simple, well executed and consistently good,” he says. His recommendations reach beyond Healdsburg to the coast. “I also love driving out to Point Reyes with my wife and going to Hog Island Oysters. We’ll usually order a bottle of white wine, sit outside, enjoy the view and take our time. It’s hard to beat that.”

Roof 106 at The Matheson is a go-to for Katz, named Wine Enthusiast’s 2025 Winemaker of the Year. “Overlooking historic Healdsburg Square, it has a wonderful atmosphere, some of the best cocktails in town, a fantastic local wine list, terrific wood-fired pizzas, steaks, and creative appetizers.” Katz collaborates with chef-owner Dustin Valette on Valette Wines.

Mexican food features on all three lists. Howland recommends a trip to El Molino Central in Boyes Hot Springs. “There’s no place quite like El Molino Central. I especially love their chilaquiles on the weekends,” he says. “They nixtamalize and grind their own corn for the tortillas, and the flavors are authentic and vibrant.”

Back in Healdsburg, Katz heads to El Milagro for margaritas and guacamole. “They do both well. It’s very casual and a great spot for the family, too.”

“The restaurant in the back of Casa Del Mole near SingleThread is incredible,” says Connaughton of the Mexican grocery store. “And Healdsburg has several great restaurants for Mexican cuisine including Gallina d’Oro, Taqueria El Sombrero, and my favorite carnitas tacos at Taqueria Guadalajara.”

At Montage Healdsburg, Katz likes the patio at Hazel Hill, overlooking the resort’s vineyards. He’s particularly fond of Aperture’s Montage Estate Sauvignon Blanc, rosé, and hillside Cabernet Sauvignon, made from the resort’s vineyard, which he designed in 2019.

“For a truly special occasion, one of the greatest restaurants in the world happens to be right here in our little town of Healdsburg: SingleThread,” says Katz. “It’s the first Michelin Three-Star restaurant in Sonoma County’s history, and a wonderfully romantic special-occasion spot.”

The Wine Spots to Know

“My wife and I recently visited Robert Young Estate Winery, and the setting is spectacular. The tasting room sits on a hill with beautiful views across wine country. You could almost imagine yourself somewhere in Tuscany, Piemonte or Bordeaux,” says Howland of the Alexander Valley estate. “We also love visiting friends at Bacigalupi, Aperture, Croix, and Small Vines. The wines here are incredible, but what I enjoy most are the people behind them. Families open their doors, share their wines and tell you their stories. That sense of community is a big part of what makes Sonoma so special.”

“The outdoor tasting under the oaks at Reeve Winery is very special!” says Connaughton. “So many great places to taste wine locally, though, like Kistler, Occidental, Lynmar, Aperture, and many others.” Occidental visits require an appointment and are available to mailing-list members with a purchasing history. In Healdsburg, he also recommends LIOCO, Marine Layer, BloodRoot, and Arnot-Roberts.

Where to Unwind

True West Film Center near the plaza is Howland’s date-night suggestion. It screens classic films and new releases, with a local wine list and cinema-approved food from neighboring restaurants. “It’s a great way to end a day in Healdsburg, and it has that nostalgic feeling of going to the movies that I love. I’ve taken my wife there a couple of times for date night, and we always have fun.”

Armstrong Redwoods State Natural Reserve near Guerneville is another place Howland recommends. “There’s something incredibly peaceful about being surrounded by those gigantic trees. We’ll bring food, find a picnic table, read, play board games and disconnect. No internet, just nature and time with family. It’s one of my favorite places to reset.”

For visitors with access to a kitchen, Young recommends stocking up at Healdsburg Farmers’ Market. “People are always blown away by the quality of the ingredients we have access to here in Sonoma County.” The market meets at the Foley Family Community Pavilion, with a Saturday season running April through December and a Tuesday season from May through September. Vendor availability changes with the season.

“I always stop at Dry Creek Peach & Produce for their extraordinary peaches,” says Howland. “Duncan’s Mushrooms are fantastic, and I also love The Handsome Carver for their fresh nut butters, particularly the pistachio and chocolate hazelnut. The farmers’ market is one of my favorite ways to spend a Saturday or Tuesday morning. You meet the people behind the food, see what’s coming into season and feel connected to the community.”

“Spend time at farmers markets or with local farmers developing a relationship and get from them the absolute best produce that is in peak season,” says Connaughton. “That makes cooking good food very easy!”