Downtown Healdsburg is the rising star of Sonoma wine country destinations. In the past decade, Healdsburg has evolved from a cozy, slow-paced town into a gourmet haven with 30 wine tasting rooms and a multitude of dining options from high-end restaurants to ice cream parlors. The bustling boutique shops and art galleries add panache to the central plaza and six-square block radius of downtown.
During a day trip to Healdsburg, we saw locals and tourists, couples and families enjoying the downtown scene. We focused on two wineries and two restaurants to highlight the destination which is a thriving gastronomic hub.
Idlewild Wines
A three-minute walk off the central plaza to Idlewild Wines evolved into a journey of gourmet specialties evoking Piedmont, Italy. David Drummond ended his law career as Chief Legal Officer at Google and now thrives in his role as proprietor of Idlewild Wines. With managing partner and winemaker Sam Bilbro, Drummond produces Piedmontese-style wines from Mendocino grapes. Drummond also owns Overshine Wine Co. and the Comunità label offered on Westside Road in the Russian River Valley.
The Idlewild tasting room hosts a spacious patio. The cozy front tasting room with comfortable window seating invites you to share fine wine and outstanding Italian-centric nosh on charcuterie boards. There is also a casual setting in the back room.
The winemaking at Idlewild starts with organic grapes and emphasizes minimal interventions. With an aromatic nose like a Riesling and lovely complexity on the palate, the Arneis white wine was a refreshing start to the tasting. The Grignolino, a lighter red, presented strawberry notes. A fruit forward Barbera and a Nebbiolo made in the Italian style but grown in sunny Calif. yielded a powerful yet juicy Nebbiolo. The expansive charcuterie board offered fresh sliced pistachio mortadella, fennel salumi, Italian cheese, and high quality, tinned Italian sardines which paired well with the wines.
Willi’s Seafood and Raw Bar
We walked a few blocks to Willi’s Seafood and Raw Bar which generated a happy vibe from the receptionist to the server and the big smiles from the cooks shucking oysters at the raw bar. The stylized fish logo on the menu and above the entrance door has a smile, too.
[ Chilled Seafood cooks
The two-story restaurant is filled with floor-to-ceiling windows, and the large patio is partially hidden from the street. Opened a year after Willi’s Wine Bar made a splash as the first restaurant from the prolific Stark family, Willi’s Seafood and Raw Bar launched in 2003. The Stark Reality Restaurant Group now owns eight Sonoma County restaurants.
Stark eateries offer a wide choice of food within each concept from French bistro to steakhouse. The latest Stark outpost, Grossman’s Noshery and Bar in Santa Rosa, is a full-on deli. At Willi’s Seafood, executive chef-co-owner Mark Stark captures his Maryland-Chesapeake Bay heritage with steam pots of Little Neck clams. Maine lobster rolls are a major draw at Willi’s. Their love of South American cuisine manifests with dishes such as ceviche with Rocoto chili which is native to Peru.
We sampled a few items of interest from Willi’s nine-section menu. The oysters from the Chilled Seafood section were fresh and flavorful. We then dove into the crudo option of charred ahi with cucumber, avocado and truffled soy. We quickly begged for more shrimp chips to scoop the bright, savory sauce.
The crispy pork belly selection from the Street Tacos section arrived with an umami-rich sauce of caramel, cucumber, cilantro and chilies. The star of the Small Plates section was the caramelized butterfish with miso vinaigrette and exotic mushrooms. Desserts looked tempting, but we set off for another wine tasting near the square.
Williamson Wines
The things to know about Williamson Wines’ co-owner Bill Williamson are that he is a storyteller and a romantic with a passion for food and winemaking. Many of his wines have love-adjacent names like Amour Merlot and Embrace Grenache. Food pairings range from the Wine & Cheese Tasting and the Icon five-course, small bites tasting to the full-on Icon Wine Pairing Lunch, and on Fridays, Epicurean lunches. The Williamson Yoakim Bridge Estate Tasting Room in Dry Creek Valley, Sonoma County, offers food options plus periodic special experiences with Bill Williamson and his wife Dawn.
Before our Healdsburg Icon Tasting began Marc DeCoulade, Operations Manager, uttered a true statement, “Bill does not believe in small portions.” An Australia native, Williamson started, and then sold a high tech company, and currently owns or leases 32 vineyards, and emphasizes education about winemaking and cooking. Colin Curtis, the Williamson chef, is named on the tasting menus. Williamson Wines Epicurean Kitchen YouTube channel, rolling silently in the tasting room, features Curtis’ handiwork.
Williamson grapes are grown sustainably, and the wines contain few sulfites. Fizz, the welcome sparkling wine, paired well with mango ginger Stilton cheese. The shrimp spring roll with Gertie Gewürztraminer was toothsome and filling. Our top pairing was Tickled Pink Rosé and spring risotto with fresh peas, asparagus, mascarpone and pecorino cheese. Paired with Entice Cuvée, the grand finale was a peanut butter buckeye.
After this fulsome tasting, we walked around the plaza to explore the offerings at the various shops from kitchen wares to gifts, books and paper goods.
Roof 106 at The Matheson
Dustin Valette opened Valette restaurant on a corner of the plaza in 2015 in a restored 100 year-old building that once housed his Great Grandfather’s bakery. In 2021 he opened The Matheson in the center of the plaza, known for duck, pork chops, and Chef Valette’s ‘Trust me’ Tasting menu. The Matheson and Valette are both noted in the 2025 Michelin Guide as restaurants with high quality food.
On the rooftop of The Matheson is Roof 106, a trendy and buzz-worthy lounge with small plates and pizzas. Located on the rooftop, the lounge features a horseshoe bar, with fire pits and comfortable couches overlooking the plaza. Yes, the address is 106 Matheson St.
But first, to the left of The Matheson entrance is the busy Wine Wall. After purchasing a card to insert into the dispensing unit, one selects the preferred size, a taste (or a “splash” as listed on the unit), half or full glass A splash of Valette Russian River Chardonnay made by David Ramey cost $7.00. My friend quickly spied the Domaine de la Romanée-Conti 2018 Pinot Noir from the Burgundy Grand Cru Romanée-Saint-Vivant. At $180 a taste, the wine was an out-of-reach selection, but no doubt was worth the taste. Knowledgeable sommeliers stood by to answer questions.
We dragged ourselves away from the Wine Wall to walk upstairs for a light dinner at Roof 106. We turned to a La Chingona pisco cocktail for my friend which may convert non-pisco drinkers by the quality of the liquor and pineapple notes. The play on words attracted me to the Roof one-Oh-Spritz with Aperol, Campari, prosecco, and a dash of rosé.
From the Plates menu we chose crispy Brussels sprouts with piquilla pepper vinaigrette and garlic chips which held a hint of spice.
The stellar pairing of burrata with black truffle, porcini, and candied hazelnuts on a sourdough flatbread delivered a textural and umami delight
We saved room for a slice of Italian sausage pizza packed with pickled peppers and fresh crushed tomato and took home the rest.
There is much more to see and taste in Downtown Healdsburg from the well-regarded Noble Folk ice cream and pie bar to Single Thread, a three-star Michelin restaurant with farm fresh, Japanese-inspired food. A gourmet day trip is an excellent appetizer to explore the area. Next visit, we will make it a weekend.
Photo credit to the author. Cover photo by Joss Flanzbaum.
#Idlewild Wines # Willi’s Sesafood and Raw Bar #Williamson Wines #The Matheson #The Matheson Wine Wall #Roof 106