Where to Eat, Stay, and Play in Healdsburg, California

In Sonoma County’s most charming town, an easygoing escape for wine aficionados and outdoor enthusiasts alike.
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Matthew Millman

Once a sleepy hamlet in the heart of northern Sonoma County, Healdsburg is now a booming culinary and wine capital. Despite several splashy restaurant and hotel openings in the past year, however, it maintains a breezy vibe that makes for relaxed weekends in wine country. More rustic than its glitzy neighbor Napa Valley, this pretty town of over 11,000 is recognizable for its restored Queen Anne homes and California farm houses. Equally charming is the walkable downtown and historic plaza, lined with galleries, shops, restaurants, and wine-tasting rooms.

Most everything you’ll eat and drink here comes from surrounding Sonoma County, including halibut and Dungeness crab caught off the Pacific Coast and produce from numerous small farms. For some real local flavor, hit the Healdsburg Farmers’ Market, held on Tuesdays and Saturdays. Whatever you decide to do, here’s everything you need to know about Healdsburg, including the best restaurants, places to stay, and ways to spend your time.

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Getting to and around Healdsburg

Healdsburg is about 65 miles north of San Francisco. While there are ways to get here from the city via public transport (take the Airport Express bus from SFO to Sonoma County Airport, then an Uber or Lyft from there to your hotel), you’ll likely want a car in Healdsburg for getting to the wineries and possibly the Pacific Coast. For the most options and best prices, rent a car at SFO and head north over the Golden Gate Bridge to Highway 101; just be sure to time your drive to avoid rush-hour traffic.

If you don’t have a designated driver for wine tasting, know that Uber and Lyft are available for vineyard hopping. You could also sign up for a wine tour with a driver, like the ones offered by Bohemian Highway and North Bay Wine Tours, or rent a bike at Spoke Folk Cyclery in town (though keep in mind that cycling under the influence is against California law).

Vineyards between Calistoga and Napa Valley, seen on the Sonoma Wine + Culinary Bike Tour

Gwen Kidera/DuVine Cycling

Cycling through Armstrong Redwoods State Natural Reserve on a Wine + Culinary Bike Tour 

Gwen Kidera/DuVine Cycling

What to do

Start your tour of town in Healdsburg Plaza, where you’ll find great shops like the new Ciao Bruto, which sells artisanal Italian foods alongside organic and biodynamic wines. From there, explore Healdsburg’s many wine shops and tasting rooms, including Marine Layer Wines, known for its small-batch pinot noir and chardonnay. Also worth checking out are The Drink (from two cutting-edge wineries, Rootdown and Leo Steen) and Lioco (offering a choice of wine flights in a casual, bar-like setting). When you’ve had enough wine, visit the Healdsburg Museum & Historical Society to learn more about the area’s Indigenous people and agricultural past.

While there’s much to see and do in Healdsburg proper, the town also serves as an ideal base for exploring wineries, the Pacific Coast, and more. The nearby Russian River, Alexander, and Dry Creek valleys teem with vineyards and tasting rooms, including the superb Aperture, where you can sample Bordeaux-style wines while browsing photographs by artist Andy Katz (the father of Aperture’s star winemaker, Jesse Katz).

Some local vineyards are even pairing wine with wellness activities to appeal to younger, more health-conscious travelers: At Joseph Phelps Vineyards in St. Helena, you can take a one-mile walk around the scenic ranch before returning to the winery for a seated tasting. To discover small-batch or boutique wineries not usually open to the public, book a bespoke tour with Bohemian Highway, or tour wine country in a chauffeured Tesla with North Bay Wine Tours.

You could easily spend your entire Healdsburg vacation eating and drinking—many do— but outdoor adventures also beckon, including kayaking on the Russian River via Getaway Adventures, cycling through Sonoma on Duvine’s California Couture: Wine + Culinary Bike Tour, and day tripping to Shell Beach to explore tide pools and forage for sea plants.

A spread of mezze at Little Saint

Emma K. Morris

Where to eat and drink

Opened in April 2022 by the owners of Michelin-starred SingleThread, Little Saint is an arts-and-community complex with several dining options under one roof: a cafe and bakery with delicious Saint Frank coffee, a cocktail bar, a wine and flower shop, and a plant-based restaurant, serving produce from its own farm. Even meat eaters will love the flavors here, as well as the more affordable prices when compared to SingleThread.

The Matheson is popular hometown chef Dustin Valette’s newest concept, opened in the fall of 2021. The three-level space houses a farm-to-table restaurant with both prix fixe and a la carte dinner menus (don’t miss the aged Sonoma duck); an 88-tap wine wall; and two bars, including a rooftop lounge for sipping cocktails while watching the sunset.

Downtown favorite Willi’s Seafood & Raw Bar serves creative small plates like barbecued Tomales Bay oysters and crispy tacos with crab, while Spoonbar, located in the h2hotel, offers Californian-meets-Italian fare in a delightful, open-air dining space. Other great options include Campo Fina for wood-fired pizza and bocce, and Troubadour, a gourmet sandwich shop from the same SingleThread alums behind ever-popular Quail & Condor bakery (get the turkey pesto sandwich on house-made sourdough bread).

A living room at The Madrona

Matthew Millman

The Madrona's exterior at sunset

Daniel Seung Lee

Where to stay

Once a quaint country inn, The Madrona reopened in April 2022 with a stylish new look, led by San Francisco-based designer Jay Jeffers, who’s known for his creative use of textures, patterns, and colors. Housed in a gabled Victorian from 1881, the hotel now features a mix of old (furniture from the original owner’s collection) and new (contemporary artwork, much of it created specifically for the hotel), as well as 24 rooms with details like bay windows, original fireplaces, and big balconies overlooking the hills of Dry Creek Valley. Guests here can also book one of the standalone bungalows, which are nestled among the trees on the outer edges of the property for a more private experience. Michelin-starred chef Jesse Mallgren helms the on-site restaurant, offering an innovative menu that combines NorCal and international influences and includes such dishes as salmon belly crudo and chicken paillard.

When it opened in January 2021, the posh Montage Healdsburg raised the standards for luxury accommodations in California wine country. Here, farmhouse-chic style meets modern architecture on 258 verdant acres, surrounded by rolling vineyards, native shrubs, and groves of California oak and eucalyptus trees. Freestanding, bungalow-style rooms feature clean lines, plenty of natural light, and private patios with fire pits, while a sleek spa offers nature-inspired treatments like the Harvest Honey Ginger Infusion Ritual. Guests can also learn about bees at the on-site apiary, or take a yoga class in the vineyard.

While not new, SingleThread remains a favorite in downtown Healdsburg for its wine country take on a traditional ryokan, courtesy of celebrated chef Kyle Connaughton and his wife and farmer, Katina. In addition to five Zen-like rooms, guests here enjoy multi-course breakfasts and guaranteed reservations at the three-Michelin-starred restaurant on Thursday through Monday evenings. Most dishes on the Sonoma-meets-Japan, kaiseki-style menu feature ingredients from the Connaughton’s nearby farm and arrive at your table on dinnerware handcrafted by Japanese artisans.

Another time-honored stay is the elegantly minimal Hotel Healdsburg, which helped put Healdsburg on the culinary map when it opened in 2001. It’s home to the upscale Dry Creek Kitchen and remains a stellar place to stay and eat.