Sonoma Wine Country: Healdsburg Dining

Jacqueline takes a trip to Sonoma wine country and finds great food to match with the wine.

Sonoma is full of great wines. We know this already. But what about the culinary scene? On a recent trip, several of my dining experiences turned out to be quite impressive and left me more excited about visiting Sonoma wine country than ever before.

For most of my trip, I stayed in the charming town of Healdsburg, located in the northern part of the county. This is where I would spend mornings and evenings wandering the streets around Healdsburg Plaza, the town square. What was I in search of? I’m not sure (unless it was coffee). But what I found on a few of my nighttime outings were several rooftop bars and classic wine country restaurants that made this Miami girl hungry for more.

Finding Height in Healdsburg

The Rooftop at Harmon Guest House

Right in the middle of town is a quaint hotel called Harmon Guest House, named after Healdsburg’s founder, Harmon Heald. The building isn’t that tall, but the views from The Rooftop bar in the evenings are pretty dreamy.

I got there right at the very end of sunset on a February evening. The open-air bar has views of the town, overlooking Healdsburg Plaza, and the surrounding mountains, which, by this point, were silhouetted by the orange glow of the setting sun. The outside seating is comfortable and protected from the northern California nighttime cooldown by heaters placed throughout the tables and couches. I chose a seat along the outside wall so that I could enjoy the view.

The atmosphere is inviting. This is a relaxed place to meet friends or enjoy a solo night out – I experienced both of these scenarios during my stay. The music was early 2000’s pop rock, and very much my style.  

As for drinks… The Rooftop offers a mix of craft cocktails, beer, and California wines; Sonoma-heavy, as it should be. I opted for a Russian River Valley Cabernet Franc. It was a delight to pair with the chill in the air, mountain sunset views, and a warm, friendly vibe together with the soundtrack of my adolescence.

227 Healdsburg Avenue

Roof 106 at The Matheson

The Matheson is a trendy addition to the Healdsburg dining scene. It is also right there in the middle of town, offering a fine dining feel in a super casual environment. Let’s call it “casual chic.”

The downstairs restaurant features “pour yourself” wines by the taste or glass, and the options are plentiful. This type of system gives guests the opportunity to taste unique and more expensive bottles, like a glass of the famed Vérité wines. The menu covers everything from Kona Kampachi Ceviche to Aged Sonoma Duck, with an emphasis on locally sourced ingredients. Chef Valette (of nearby Valette) is running the culinary show, and his creative expertise shows in each dish presented here.

Upstairs at Roof 106, guests can order fresh Ahi Tataki or one of Chef’s famous pizzas. (I recommend the House Cured Pork Belly, Gruyere, Roasted Garlic Crème Fraiche, Red Onion pizza.)

The rooftop is indoor-outdoor with a big bar in the center of the indoor portion, accompanied by plush couches along the wall. Outdoor seating features private fire pits and heating lamps for extra warmth.

Again, the wine list leans Sonoma with a few Mendocino selections from the county to the north. However, I did see Muscadet, Rueda, Bordeaux, Jura, and Tuscany, among other European favorites represented, too. This is truly a worldly rooftop experience, with all the coziness of small-town wine country – and DELICIOUS pizzas.

106 Matheson Street

Grounded & Great Eats in Sonoma Wine Country

Dry Creek Kitchen

No trip to Healdsburg is complete without a visit to Dry Creek Kitchen, a Charlie Palmer restaurant.

This “Progressive American” restaurant also features seasonal dishes alongside local specialties and even a chef’s tasting menu.

I enjoyed the Double Cut Heritage Pork Chop, served with Tokyo Turnip, BBQ Bernier Squash, Charred Leek and Sherry Jus. Let me tell you it was perfect alongside my Sonoma Cabernet Franc (the second of the evening).

Make sure and ask about the dessert wine pairings. This is your opportunity to try a fortified Chenin Blanc or Chardonnay, late harvest Viognier or Sauvignon Blanc, or a port-style wine all from nearby wineries. These are served as tastings with paired desserts like Dry Creek olive oil cake, Rum Baba, or warm butter cake. The best one on the menu is the Brûléed Cowgirl Creamery Mt. Tam featuring poached pear, pistachio shortbread, and fennel pollen. This last one is paired with the fortified Chardonnay “Ratafia” by J Winery, and it was an outstanding finish to the night.

317 Healdsburg Avenue

BarnDiva

BarnDiva was recently awarded a Michelin star, but this isn’t why you should make a reservation to go. This is a perfect spot for a courtyard lunch of “modern country cuisine,” which means Hamachi Crudo, Cacio e Pepe, BD burger, or a fried chicken sandwich. All up to Michelin standards, of course. We had some pretty impressive little goat cheese croquettes drizzled with honey.

The wine program not only consists of an impressive international list including half bottles and large formats, but also wine events and dinners throughout the year. The list is sectioned out by grape variety (helpful) and then even further by region. I had to fight myself not to gravitate toward my usual Sancerre or Chablis for lunch, but instead decided to continue drinking local and went with a Peay Viognier from Sonoma Coast.

BarnDiva is an excellent addition to your Sonoma wine country dining whether Healdsburg is your final destination, or you’re just passing through.

231 & 237 Center Street

Read more about wine country and culinary destinations in our Travel section.