This local favorite has been serving up food from Oaxaca and Jalisco for more than 40 years. The interior is spacious with a central bar and a small handful of seats, but you should sit on their excellent patio when the weather is great (which is almost always in Healdsburg). Don’t miss their mole oaxaqueño, a rich chile-chocolate sauce incorporating more than 20 ingredients, that’s especially delicious heaped on top of carnitas.

If you’re about to dive headfirst into Healdsburg’s wineries, you’re going to want to be prepared, and a full stomach of BBQ is the kind of prepping we can get behind. Customize your BBQ platter at Kin Smoke with a bunch of meats, including brisket and St. Louis-style ribs, plus sides like bourbon baked beans and fried pickles, all served with their tasty cornbread. It all gets piled up on a tray ready to be eaten in the casual space with a handful of TVs playing whatever game’s on that day.

For the perfect breakfast before heading out on a wine-tasting spree, head to The Parish Cafe for New Orleans-style comfort food that would make even the most homesick Louisianan proud. Grab their pillowy fried beignets dusted in powdered sugar and pair them with chicory coffee to be transported right to NOLA, or dig into a more hearty breakfast like their breakfast po’boy or shrimp and grits. Lunch is all about seafood po’boys, but they also serve other Cajun classics.

Known for cocktails and small plates perfect for sharing, Lo & Behold is a relaxed option perfect when you’re in town with a group of friends. Grab a guava paloma or cucumber-fennel mezcal cocktail, then split a world tour of plates like Sichuan-spiced pork spareribs, bánh xèo with pork belly and shrimp, and dukkah-spiced grilled halloumi. The dining room has an industrial-meets-rustic feel with a gorgeous bar at its center, whereas the patio is a private, canopy-covered garden escape.

Willi’s is a casual spot in downtown Healdsburg that’s always busy around lunchtime, bringing together Latin flavors and New England-style seafood in a way that just works. Oysters are the name of the game here: try them barbecued in the traditional Tomales Bay-style, or opt for a variety of raw oysters from near and far. For your entrée, grab a New England-style lobster or crab roll, or try their selection of ceviches, crudos, and seafood tacos.

At Bravas, you’ll find traditional Spanish tapas like pan tomate, patatas bravas, and chicken croquetas, alongside more creative options like clams steamed in cava and crab-stuffed peppers, as well as larger dishes including paella. This low-key tapas bar is buzzy at night, so it’s great for a group who enjoy adding to a lively hum of conversation in the background. We tend to skip the main dishes and load the table up with tapas instead.

If you want to grab something quick to have on hand before hitting the wineries, drop by Troubadour Bread & Sandwiches. The excellent bread is baked in-house, and the thick sandwiches filled with options like pastrami, chicken salad, and goat cheese with pesto and vegetables are sturdy enough to last a few hours while you visit a few wineries. They’re perfect for a picnic lunch between wine-tasting stops or to nibble on as you wait in traffic on the drive home.

If you’re looking for a vegan option, Little Saint is a new, intriguing spot in Healdsburg. Sit outside on the patio for table service at the restaurant, or head inside to grab something quick: this food hall-style venue houses a cafe, marketplace, and bar all under one (vegan) roof. It’s run by the same owners as SingleThread, so it’s an option if you want a more casual and budget-friendly introduction to their thoughtful approach to produce.

A family of winemakers is behind Journeyman Meat Co, where they pay just as much attention to salami and charcuterie as they do to their wines. All the charcuterie is made locally in Sonoma County, and is perfect for an on-the-road picnic or to stash in your luggage for the trip home. The sandwiches are near-perfect and made to order—we like the smoked sausage sandwich with garlicky aioli, roasted peppers, and fennel.

In a town filled with coffee shops, it’s hard to pick just one, but we keep coming back to Black Oak Coffee Roasters. Their single-origin pourover coffee is prepared flawlessly to bring out subtle flavors, and they also have inventive lattes infused with lavender, spiced brown sugar, and wildflower honey with bee pollen. And if you’re hungry, there's a menu of tartines, breakfast burritos, chia puddings, and more. The pastries are great too, especially the jalapeño cheddar scone.

This upscale restaurant takes note from Japanese traditional fine dining, with attentive-but-unstuffy service and beyond-elegant plating. Embracing the kaiseki style, diners start with a playful selection of amuse-bouches and then move through a progression of 10 courses that bring together the owner-chef’s Japanese training and locally-grown produce from the restaurant’s farm. Dishes change constantly and are in tune with the seasons.

Barndiva serves up creative seasonal dishes in a rustic barn-inspired setting. The patio is the perfect spot for late lunch or early dinner, beautiful but not overly romantic, so it works equally well for a group of friends or a date. If you want a more intimate setting, grab a table indoors. The menu changes monthly to best incorporate seasonal local ingredients, but it’s important to start off a meal here with the famous, always-on-the-menu goat cheese croquettes.

There are two parts to The Matheson: a more formal dinner spot on the ground floor, and Roof 106, a more casual option on the (you guessed it) roof, open for both lunch and dinner. Downstairs, you’ll find a menu full of local seafood and seasonal produce in a huge dining room with a sweeping view of the full bar and open kitchen: if you’re dining solo or in a party of two, grab a bar seat facing the kitchen to watch the chefs work their magic.

Located off of Westside Road, one of the best stretches of Healdsburg’s wine country, the Madrona is a hotel in a Victorian-era manor that recently reopened after a lengthy renovation. Its restaurant’s menu was updated as well in the overhaul, definitely for the better. It used to be pretty fussy, but the menu now puts an elevated twist on comfort food, with dishes like salmon belly crudo, potato gnocchi with a duck bolognese, and chicken paillard with spiced brown butter.