The stream of accolades for Healdsburg continues, the latest arriving from geography-focused website WorldAtlas, which recently named the northern Sonoma County city the friendliest small town in California, citing its welcoming vineyards, lively jazz festivals, charming 19th-century inns, art scene, unique lodging options and wine tasting experiences.
Set at the confluence of the Russian River, Dry Creek and Alexander valleys, Healdsburg has earned its reputation as a polished yet approachable base camp for exploring Wine Country. For travelers planning a return — or a first visit — the following stops offer a well-rounded introduction.
Wine Tasting in Healdsburg
With three renowned wine regions converging at its edges, the town presents an embarrassment of riches for oenophiles.
Bacchus Landing (14210 Bacchus Landing), a contemporary compound just minutes from the Healdsburg Plaza, is home to multiple boutique producers — including Aldina, Comstock, Convene by Dan Kosta, Dot Wine, Solo Nostro and Smith Story Wine Cellars — making it possible to compare styles without moving the car. The central piazza often hosts live music and community markets, giving the experience a festive air.
Medlock Ames (13414 Chalk Hill Road) pairs organically farmed Bordeaux-style wines with an immersive sound experience. Guests can wander the 338-acre Bell Mountain Ranch while listening to an audio program, recorded onsite, that culminates in a guided tasting of five wines that underscores the winery’s sustainability ethos.
At Aperture Cellars, Jesse Katz, named Winemaker of the Year in 2025 by Wine Enthusiast, focuses on meticulously crafted blends and single-varietal bottlings. The sleek tasting room doubles as a gallery space for large-scale photography by his father, Andy Katz, adding a visual counterpoint to the wines in the glass from labels Devil Proof, Collage and Aperture.
Where to Eat in Healdsburg
Restaurants here reflect the surrounding farmland, with menus shaped by the seasons.
Across from the Plaza, The Matheson (106 Matheson St.) houses two restaurants under one roof. On the ground floor, the main dining room presents refined, ingredient-driven plates. Upstairs, Roof 106 offers a more casual experience with pizza, small plates and cocktails, as well as an open-air vantage point over town. The location has special meaning to chef Valette; his great-grandfather operated his first Sonoma County bakery here almost a century ago.
Executive chef Shane McAnelly has built a dedicated following since taking over the reins at Dry Creek Kitchen (317 Healdsburg Ave.). Guests can opt for a three-course seasonal menu or a lengthier tasting progression, including a pasta-focused option. Whichever you choose, save room for dessert crafted by pastry chef Taylor Kelley.
It’s Oktoberfest every day at Tisza Bistro (165 Healdsburg Ave.), a German-Hungarian restaurant that turns out excellent Bavarian pretzels, housemade bratwurst and a variety of schnitzels. Open for lunch and dinner; closed on Tuesday and Wednesday.
Little Saint (25 North St.) showcases the range of plant-based cooking in a sleek, spacious building that also houses a coffee bar, a wine lounge and a cocktail bar. Its intimate events space is fast becoming one of the hottest music venues in the country, with performances by artists such as Beck, Rufus Wainwright, and Phoebe Bridgers, Lucy Dacus and Julien Baker of boygenius; plus, an upcoming show by St. Vincent. Programming includes free live music every Thursday night.
Arts and Culture in Healdsburg
Wine and food may draw visitors, but the arts help persuade them to linger.
The recently opened True West Film Center (371 Healdsburg Ave.) screens new releases and classics, as well as special programming carefully curated by John Cooper, the former director of the Sundance Film Festival.
At The Harris Gallery Art & Wine Collection (320 Healdsburg Ave.), paintings by M.C. Harris and his son, Alexander Harris (who goes by A3l3xzand3r), are displayed just steps from the Plaza, often accompanied by pours from the family’s wine label.
In Healdsburg, even hotels participate in the creative exchange. Harmon Guest House (227 Healdsburg Ave.) integrates rotating works by local artists throughout its public spaces, inviting guests and passersby alike to treat the hotel as an informal gallery. The property’s Art Walk website serves as a handy guide. Head to The Rooftop for bites, cocktails and views of the Sonoma hills, Fitch Mountain and downtown Healdsburg.
Stay the Night in Healdsburg
If a day trip feels rushed, check into one of Healdsburg’s charismatic hotels.
The Cottages at Little Saint (425 Foss St.) comprises four vividly redesigned guest cottages, courtesy of creative director Ken Fulk. Tucked into a quiet neighborhood near downtown, they extend the ethos of its sister restaurant into residential form.
Appellation Healdsburg (165 Foss Creek Circle) is the flagship property of chef Charlie Palmer’s new hospitality company. Here, the emphasis is culinary from the outset, with an on-site restaurant upon entry and a rooftop bar with expansive views. In addition to its 108 rooms and suites, the property features a spa and a fitness center.