‘It was just a little farm town,’ locals tend to say when speaking of “old” Healdsburg (just over twenty years ago). That’s no longer the case, as evidenced by the Healdsburg Wine and Food Experience (HWFE), the first international wine and food event in northern California, now in its third year. The event, which features a wide array of wine tastings, food pairings, cooking demonstrations, and live entertainment, is more popular each year, according to HWFE’s Founder, Steve Dveris. “It’s a celebration of Healdsburg’s agricultural history and the town’s transformation into a food and wine destination. It’s also a platform to raise money to support local agriculture, do good, and elevate Sonoma’s chefs, restaurants, and winemakers,” Dveris said.

Healdsburg and its surrounding areas, which include Dry Creek Valley, Alexander Valley, and Russian River Valley AVAs, have become a global magnet for foodies and wine connoisseurs. What began as a tranquil town has emerged as a shining star of California’s wine country, earning recognition for its exceptional wine and food culture.

Healdsburg’s journey began in the mid-19th century when pioneers like the town’s namesake, Harmon Heald, came west dreaming of gold and the promise of land. At that time, the agricultural area was known for prunes and apples long before its vinicultural heyday. In the late 20th century, Healdsburg’s trajectory took a dramatic turn. The wine industry, steadily gaining momentum in neighboring regions like Napa Valley, began to spread its roots deeper into Sonoma County.

FIRST WINE FAMILIES

Among those who played pivotal roles in Healdsburg’s rise to wine prominence were the Seghesio, Passalacqua, and Young families. Francesco Passalacqua emigrated from Genoa, Italy, in 1865 and settled in Healdsburg, where he immediately planted grapes. Since 1858, six generations of the Young Family have lived and farmed the Young ranch, now the Robert Young Estate Winery, and they were the first to plant Cabernet Sauvignon in the Alexander Valley AVA. Seghesio Family Vineyards planted its first vines in 1895 and was one of only 100 wineries that survived Prohibition by continuing to grow and sell grapes, grape juice, and grape concentrate. // www.seghesio.com // www.passalacqua.com //  www.ryew.com

As the wine industry thrived, Healdsburg’s cultural and culinary scene also flourished. Buildings around the Plaza became art galleries, quaint shops, and gourmet restaurants, and today, Healdsburg is a vibrant mix of historic small-town America and worldly modernity. The town’s transformation into a wine and food destination has attracted visitors and inspired local businesses to innovate and elevate their offerings.

Here is an examination of the town’s now-classic restaurants, some of its most recent restaurants, wineries, and tasting rooms, and some innovative concepts that have added their flair to ‘The Burg.’

THE CLASSICS

Dining at the three-Michelin-starred Single Thread Farm Restaurant and Inn is an experience. Its 11-course tasting menu is based on the Japanese concepts of kaiseki—elaborate multi-course meals crafted as art—which has put this restaurant on the international gastronome radar and brought massive attention to the tiny town. // www.singlethread.com

Barndiva is renowned for its beautiful garden terrace that hosts events like the annual Pink Party, which highlights local rosé wines, each spring. This farm-to-table American eatery gets its name from its barn-like structure and its attitude. The Michelin-guide restaurant emphasizes using artfully prepared, local, seasonal products; hence, its motto, “Eat the View.” // www.barndiva.com

Rodney Strong Vineyards is not only a Healdsburg classic, but the founder also planted the first Chardonnay in what is now known as Chalk Hill AVA, just outside town. It was also the first carbon-neutral winery in Sonoma County and was named Wine Enthusiast’s Winery of the Year in 2013. // www.RodneyStrong.com

Charlie Palmer’s Dry Creek Kitchen’s upscale American cuisine and top wine selections consistently draw crowds and acclaim. Pro tip: Ask for an outside dinner table for an intimate and slightly magical experience after sunset. // www.drycreekkitchen.com

Pizzando is Healdsburg’s homey neighborhood Italian hangout. Creator and native Italian Paolo Petrone’s menu highlights every region of Italia. It focuses on a new Italian area’s cuisine and wine each month, like Pizza Caponata with Sicily’s Nerello Mascalese or Spaghetti alla Bottarga with Vermentino from Sardinia. //  www.pizzandohealdsburg.com

Carlos Mojica’s Latin fusion restaurant Guiso’s popularity has exploded as locals have spread the word. Caribbean, South American, and Central American cuisine mix with Latin culture and locally sourced products for standout dishes like Caribbean-style paella and pupusas (corn tortillas filled with vegetables or pork and cheese. // www.guisolatinfusion.com

Farmhouse, just outside town, recently revamped its menu to the ultimate epicurean experience with curated pairings like Dungeness Crab and Vincent Joudart Brut Reserve Cote de Blancs Champagne. The Apple Mooncake with 2005 Chateau Raymond-Lafonen Magnum Sauternes is a hands-down winner. //
www.farmhouseinn.com

Bravas Bar de Tapas is a popular spot for cocktail hour. It offers red, white, or sparkling sangria, traditional Spanish tapas, modern tapas, and paella in a cozy off-street courtyard with an outdoor bar. // starkrestaurants.com/stark-restaurant/bravas-bar-de-tapas/

THE NEWBIES

Several new establishments have emerged recently, like The Matheson by Dustin Valette, who also owns the classic restaurant Valette. The three-story restaurant includes a 10-seat omakase bar called Sushi by Scratch, rooftop dining at Roof 106 with views of the Healdsburg Plaza, a main-floor cocktail bar, a wine wall, and a full-service restaurant with dishes like California Halibut, a succulent filet served with summer veggies in a bright citrus beurre blanc sauce. // www.thematheson.com

Quail & Condor’s Chef and Co-Owner, Melissa Yanc, was the Season 6 winner of Food Network’s Holiday Baking Championship, and she brought her extraordinary baking skills to the lucky residents of Healdsburg. The options are outstanding and baked fresh daily: Challah, Kouign Amann, Super Seeded Pan Loaf, Olive Campagne, and more. // www.quailandcondor.com

The Quail and Condor folks also opened Troubador Bread & Bistro, which offers a French café menu at lunch and a prix fixe dinner menu with options like Halibut en Blanc with white asparagus, onion soubise, and sauce blanc. // www.troubadourhbg.com

Goodnight’s Prime Steak + Spirits began as a steakhouse and recently added a plant-based menu. In addition to the best steak menu around, Executive Chef David Lawrence concocted tasty items like Whole Roasted Cauliflower Muhammara, featuring za’atar, local olive oil, crème fraîche, and toasted walnuts. // www.goodnightsrestaurant.com

Ernest Vineyards is right on the square, but its fruit comes from the highly coveted terroir of Mendocino County and West Sonoma Coast. Check out the Aligoté and rarely found variety Petite Arvine, sustainably grown and expertly crafted. // www.ernestvineyards.com

NEW CONCEPTS

Healdsburg has become a destination for digital nomads, so it was logical that some soothsayer would design a modern concept co-working space downtown. Founder Jim Heid did that with 4500 sq. ft. Craftwork, offering glass-walled offices by the day, month, or yearly membership. It’s become a hub for entrepreneurs and social butterflies tired of working alone at home, and it has a gathering and meeting space for work and after-hours events. // www.craftworkhbg.com

New Tree Ranch is only steps outside town but so secluded that it feels hundreds of miles away. Its two luxury villas house six guests each and are strategically placed to give each group complete privacy. It’s the ultimate in luxury wellness tourism. Departures Magazine has recognized it as one of the 10 Luxury Experiences for Eliminating Negativity in the New Year. //www.newtreeranch.com

Healdsburgians were effervescent with excitement when Bubble Bar opened in early 2024. The popular sparkling wine spot offers a thoughtfully curated selection of sparklers from around the world. // www.healdsburgbubblebar.com

NEW WINE SPOTS

Bricoleur sits on a massive property between Healdsburg and Windsor, with a gigantic barn as the center point of gardens, vineyards, guest houses, and structures rentable for events. But it’s the chef-prepared, multi-course, immersive wine and culinary experiences that blow patrons away. On the casual side, the Essentials Picnic gives guests a red wagon with air tags, so replenishments can be brought to them wherever they are on the vast estate. // www.bricoleurvineyards.com

Orsi Family Vineyards took over an existing winery location steps from town and started their own label with the fruit they’ve grown in the area for decades. They lead with their Italian family heritage, offering little-known Italian varieties like Biancolella, Sagrantino, and Schioppettino. This year, they introduced their first sparkling wine, Spumeggiante Oro, made with Biancolella. // www.orsifamilyvineyards.com

Just down the road, what was Armida Winery is now under new ownership with a new name: Overshine Wines. The Overshine group also acquired Idlewild Wines and introduced a third label, Comunità, which will showcase Italian varieties grown at Las Cimas Vineyard in the Russian River Valley. // www.overshinewines.com

SLEEPING SPOTS

Locals often point to the opening of Hotel Healdsburg in the early 2000s as the point when the town began its metamorphosis. Situated just off the historic Healdsburg Square, Hotel Healdsburg boasts a highly acclaimed spa, a 60-foot garden pool with several spaces to lounge, and luxurious accommodations, some with private terraces. It is owned by Piazza Hospitality, which also owns Harmon Guest House and H2Hotel. // www.hotelhealdsburg.com

The Madrona was originally a private home built in 1881. It was transformed into an inn and restaurant a century later and is now listed on the National Register of Historic Places. The property showcases furniture and art dating to the early 18th century. // www.themadrona.com