Modern Guide to Healdsburg: New Restaurants, Posh Stays + Wine for Days
A secret country town no more, Healdsburg is having a luxurious heyday with the arrival of high-end dining and hotel options such as the five-star Montage Resort. (Courtesy of Montage)

Modern Guide to Healdsburg: New Restaurants, Posh Stays + Wine for Days


Healdsburg is the goldilocks of Wine Country.

Quainter than Napa and ritzier than Sonoma, it has that perfect balance of luxury and small town charm we crave when visiting the rolling vineyards of Northern California. It’s no wonder the city has evolved rapidly over the past decade, from a sleepy farming community into the most visited destination in Sonoma County.

This is all to say that Healdsburg’s days as a Bay Area secret are over. In fact, the town is arguably Wine Country’s hottest destination of the moment. A surge of recent openings has captured local and national fanfare, with posh hotels like the Madrona and acclaimed restaurants like the Matheson and Cyrus vying for attention with vibrant tasting rooms, wineries, and boutiques.

Despite its booming development, Healdsburg has been able to do what Napa hasn’t, which is to maintain a sense of place, one where real people both live and work. The community wants to make sure it stays this way and continues to serve locals, too.

Located just over an hour north of San Francisco, Healdsburg makes is a perfect day trip from most of the Bay Area. If you can shell out some coin, it’s terrific for a weekend escape. Yes, a trip here can mean Michelin stars, pricey bottles of wine, and wildly expensive overnight stays. But if you play your cards right, a trip to Healdsburg can also balance high-end experiences with more relaxed choices. Don’t forget to savor a scoop of ice cream or a slice of pizza on the square, and visit the many still family-run wineries where owners will gladly pour you a few extra sips.

The Best Restaurants in Healdsburg

Chef Douglas Keane in the kitchen at Cyrus.

(Courtesy of Cyrus)


It didn't take long for SingleThread to make an impression. In 2018, the restaurant became the first Sonoma County restaurant to receive three Michelin Stars, and it did so in just its second year. Today, it remains one of only six restaurants to hold that recognition in California. The vibrant 11-course tasting menu employs techniques and philosophies inspired by founders Kyle and Katina Connaughton’s time living in Japan, and features ingredients grown on the couple’s nearby 24-acre farm. Restaurant bookings are released at 9am on the first of every month. The on-site inn is also a luxurious treat: You can order in-room dining and a restaurant reservation is guaranteed. // 131 North St. (Healdsburg),

The Matheson and Rooftop 106

This much anticipated, tri-level restaurant became an instant classic when it opened in late 2021 directly across from the town plaza. On the first floor, you’ll find a state-of the-art wine wall where you can grab a glass, swipe a card, and taste a splash or full pour of nearly 90 options; as well as the upscale restaurant led by chef and owner Dustin Valette and featuring local farmers, fishermen, and purveyors. More casual fun happens upstairs with wood-oven pizzas and vibrant seasonal cocktails on the rooftop lounge. // 106 Matheson St. (Healdsburg),

Ten minutes from Healdsburg, the return of Cyrus is arguably the area’s most highly anticipated opening of late. Chef Douglas Keane closed his original, two Michelin-starred Cyrus back in 2012 and has revived it once again with a new approach. Less focused on running a cutthroat kitchen with the sole intent of racking up Michelin stars (though, his new iteration has already snagged a star), Keane hopes to offer an enjoyable experience for both his guests and his employees by creating a higher quality, inclusive, and more fun environment. For $295 per person, guests will live it up with 20 courses in a series of different rooms throughout the evening. After starting with canapes and cocktails, diners progress to small bites at the kitchen table and larger entrees in the dining room overlooking the vineyards. Dessert is a true finale. // 275 CA-128 (Geyserville),

Little Saint
Debuted in 2022, this ambitious project aims to be more than a place to eat; Little Saint wants to be a community gathering space. The 10,000-square-foot venue encompasses many concepts: a coffee bar, a cafe and bakery, a wine lounge, and a restaurant serving 100-percent plant-based cuisine. Wines are sourced from wineries committed to responsible farming with a focus on BIPOC and women winemakers. Look out for weekly live music, book signings, film screenings, and more. // 25 North St. (Healdsburg),


If you're looking for another special occasion spot Barndiva is your place (and a popular choice for weddings). Elegant and rustic, the atmosphere screams Wine Country, with farm animal–themed artwork, antique fixtures, and a tree-covered gravel patio draped with twinkle lights that's positively hopping on weekend nights. As for the food, it's fresh, sophisticated, and beyond tasty. If you can't swing dinner, opt for an epic brunch. // 231 Center St.,

Bravas Bar de Tapas

With perhaps the best patio in town, this traditional Spanish tapas restaurant is brought to you by beloved Sonoma County restaurateurs Mark and Terri Stark (known for Willi's Wine Bar, Bird & the Bottle, and more). Bravas is lively—note the list of gin and tonics (try the Chubasco) at the outdoor bar, where they broadcast the local games—and solid for shareable plates such as duck meatball bocadillos and crispy pig ears. Finish with the goat cheese tostada for a savory-sweet dessert. // 420 Center St.,


With its wood-oven pizzas and hearty pastas, Pizzando, perched on the corner of Healdsburg’s main square, is a refreshing departure in a town full of small plates. Choose a spot inside the newly renovated dining room or the sidewalk parklet that’s perfect for people-watching, and order antipasti, Neapolitan- and Roman-style pies, focaccia, and grilled meats. End your meal with an organic soft-serve from Strauss Family Creamery. The recently revived bar offers twists on Italian-inspired cocktails and a curated selection of local wines. // 301 Healdsburg Ave (Healdsburg),


Open for a decade now, Chalkboard is chef Hugh Dyer’s casual go-to for daily menus featuring produce from local farmers, ranchers, and from his own garden. Start with small plates such as a crudo or pork belly biscuits before moving on to house-made pastas and a selection of meat and seafood. Save room for the Samoa pudding paired with a Nookutini nightcap. // 29 North St.,

Noble Folk Ice Cream & Pie Bar

This sweet little shop on the square taps into the hipster in all of us with the likes of "heritage pies" (such as the amazing chocolate maple walnut). But the deliciousness doesn't stop there. Scoops of ice cream the size of your head—in flavors such as pistachio cherry, almond matcha, and vegan passion fruit—make this the Bi-Rite Creamery of Wine Country. // 116 Matheson St.,

Parish Café

This sunny little space on the way into town from the 101 (take the Central Healdsburg exit) is a slice of the south plopped in Wine Country, and perfect for a quick breakfast or lunch before wine tasting. Pick from your poison of po'boys, share an order of fried pickles, and don't miss the beignets. // 60 Mill St.,

Healdsburg's Best Wine Tasting

(Courtesy of Jordan Vineyard & Winery)

Nearby Wineries

Nestled in the middle of some of California's top wine regions—Russian River, Alexander Valley, and Dry Creek Valley—Healdsburg is a prime wine tasting destination that many people skip in favor of Napa and Sonoma. Big mistake.

A large part of the region has made its name on producing top notch, cool-climate chardonnay and pinot noir. Family-owned Arista Winery(7015 Westside Rd) is a fantastic representation of this region's prowess, for they cut no corners when it comes to the quality of their wines. We also love MacRostie Winery(4605 Westside Rd), not just for their pinot and chard, but their gorgeous digs and panoramic views of the Russian River Valley.

Limerick Lane(1023 Limerick Ln.), a humble century-old winery, offers zinfandel and Rhone varietals in addition to pinot and chard in a refreshingly unpretentious atmosphere with stunning views.

The historic Seghesio Family Vineyards (700 Grove St) has been making wine in Healdsburg for over 120 years and is one of the few California wineries that managed to survive Prohibition. This Italian family is known for their zinfandel and Italian varietals.

For the adventurous, Healdsburg offers several options that go beyond the typical Wine Country tasting experience. At Jordan Vineyard & Winery(1474 Alexander Valley Rd.), a stunning ivy-clad chateau, you can visit winery chef Jesse Mallgren's massive gardens (and donkeys!) on a three-hour tour traversing the 1,200-acre estate. For an incredibly special day at a winery with a female winemaker at the helm, head to Sutro Wine Co.(13301 Chalk Hill Rd.), which specializes in minimal intervention, small-scale production of volcanic terroir wines. Founder Alice Warnecke utilizes grapes exclusively farmed on her family’s Warnecke Ranch. The signature tasting experience is truly soil to glass: Guests start with a 45-minute hike throughout the ranch before a relaxing tasting in a shaded oak grove or, if the weather is less than ideal, in a modern tasting room nearby on the estate.

Sparkling wine lovers should head to J Vineyards(11447 Old Redwood Hwy.), where the J Bubble Room hosts a multi-course, sit-down lunch paired with still and sparkling wines. It’s especially worth visiting for their Shifting the Lens event series, which invites chefs from diverse backgrounds to challenge the common conception of food and wine pairings.

Wine Tasting in Healdsburg's Main Square

Don't have a designated driver? Another great aspect of Healdsburg is the ability to try many wineries without needing a car. Take a walking wine tour of the town's many tasting rooms around the square. We love Siduri(235 Healdsburg Ave) for its pinots that span California and Oregon; Banshee Wines(325 Center St.), which you'll leave with inspiration for a total living room redesign; and Cartograph(340 Center St.), where you can taste wine by flight, glass, bottle, or on tap.

Where to Drink in Healdsburg

(Courtesy of @spoonbarhealdsburg)


Come here on balmy evenings when they open the retractable walls or grab a seat on the expansive back patio to indulge in market-driven craft cocktails like the Sleeping Beauty (huckleberry vodka, rosemary, lemon, grapefruit, and pickled blueberries). Seafood Sundays and fried chicken Wednesdays are also good nights to stop by. Consider yourself warned: dishes here are decadent and large, so they convince you to cancel your other dinner reservation. // 219 Healdsburg Ave.,

Duke's Spirited Cocktails

Duke's is carrying on a long tradition of slinging drinks to Healdsburg residents in a location that dates back to 1933. A true local watering hole, Duke's serves original cocktails with locally made spirits and home-grown ingredients. Try the Hot For Teacher (Death's Door gin, apple, chamomile, aquavit, Alessio Bianco) or Ms. Bojangles (Four Roses bourbon, house root beer, Fernet Branca, bitters, phosphate). Soak it up with poutine and corn dog pops. // 4113, 111 Plaza St.,

Taste of Tea

Sip sake cocktails or take a break from the booze with a Marteani (get it?) at Taste of Tea. The menu also features nine kinds of matcha, tea lattes, and scientific siphon pot infusions. Pair your beverage with ramen, rice and noodle bowls, or other Japanese bites. Stay for a treatment at the in-house tea spa, offering Japanese green tea–infused R&R. // 109 North St.,

Flying Goat Coffee

Third wavers, this is your haven for coffee as good as any found in San Francisco city limits. Their ethically sourced beans and quality roasts of have won awards for years, plus they have yummy pastries on-hand for quick stops. The Optimist's Blend will start your day on the right track. There are two locations, so if one is packed, try the other. // 300 and 419 Center St.,

Black Oak Coffee

If you’re on the hunt for a solid cup of coffee in Healdsburg, this is your spot. Located along the main square, Black Oak is spacious and cozy with comfortable seating and fast WiFi. The basic drip coffee is excellent, as are the more gussied-up options such as the lavender latte, black oak nitro cold brew, or sweet dirty chai oat milk latte. Chef Beryl Adler elevates the food menu beyond basic coffeehouse fare. Options include a soft scrambled breakfast burrito, carrot cake muesli and seasonal tartines, plus a variety of vegetarian and vegan choices. // 324 Center St.,

Where to Stay in Healdsburg

Inside the Carriage House at the Jay Jeffers–designed Madrona.

(Courtesy of The Madrona)

Hotel Healdsburg

Located mere steps from the historic town plaza, Hotel Healdsburg’s prime location is one of the stay's biggest perks. But it’s not just its proximity to restaurants, tasting rooms, and shops that make it one of the most popular choices for accommodations—the modern guest rooms, luxurious spa, 60-foot pool and acclaimed onsite restaurant, Charlie Palmer's Dry Creek Kitchen, are also big draws. // 25 Matheson St.,

The Madrona

With its eclectic decor and stunning transformation from historic mansion to posh boutique inn, the Madrona has been named one of the hottest new hotels in the country by Condé Nast Traveler. Originally constructed in 1881 as a private home for a well-to-do family, San Francisco–based designer Jay Jeffers led the massive renovation. The 24-room hotel features 250 pieces of the art and furniture original to the home, paired with luxurious new trappings for a warm and stylish vibe. Michelin-starred chef Jesse Mallgren leads the onsite restaurant, which serves locals and visitors alike for brunch and dinner. // 1001 Westside Rd.,

Montage Healdsburg

If you want to be close to the action but feel far away, Montage Healdsburg is the Forbes five-star resort—situated among oak tree groves and vine-covered hills a few miles north of the square—of your luxury-loving dreams. The 130 modern bungalow-style guest rooms and suites have been eco-consciously designed with their own outdoor oases. World-class amenities include treatments at the expansive 11,000-square-foot spa, a zero-edge swimming pool, and decadent meals at three on-site restaurants. // 100 Montage Way,

The Ruse

This stunning 11-room inn is a microcosm for what Healdsburg tourism is all about: charm, but make it luxe. The intimacy and hospitality at the Ruse are akin to the best B&Bs, but the amenities and style feel fit for a much larger hotel—think heated pool, an 18-hole Jack Nicklaus–designed putting green, six pickle ball courts, a spa, and a pavilion with a full kitchen. The Victorian Italianate mansion was originally built in 1883 and renovated in 2021. Rooms located in the main building, as well as several separate bungalows, are modern and stylish with soaking tubs and fireplaces. In the morning, you’ll be personally served by the on-site chef. // 891 Grove St.,

Harmon Guest House

From the same developers behind the eco-chic Hotel Healdsburg and H2Hotel, Harmon Guest House is named after the town's founder, Harmon Heald. A geometric and modern design masterpiece, Harmon is also sustainability super star with natural light and a bevy of amenities: free three-hour cruiser rentals, a solar-heated pool, complimentary Sunday yoga, daily breakfast, and a rooftop in town with a fire pit, bar, and panoramic views. // 227 Healdsburg Ave.,

Hotel Trio

Interested in a more practical and budget-friendly option, or perhaps looking to use points? Hotel Trio, a Marriott property, opened in 2018, so the rooms feel fresh and modern. Stays here include a complimentary breakfast buffet, two-hour free bike rental, pool and fitness center, and a lobby bar that features local wine and beer. Need something delivered to your room? On-site robot concierge Rose the Robot will bring it to you in a hurry. As Healdsburg's only all-suite hotel with full kitchens, it is also a great choice for families and large groups. // 110 Dry Creek Rd.,

Spas & Shopping in Healdsburg

(Courtesy of Spa Hotel Healdsburg)

Chill Out

Weekend R&R in Wine Country wouldn't be complete without a little chill time at the spa. Do yourself a solid and head to Spa Hotel Healdsburg (25 Matheson St), a small hideout tucked back by the private pool (ask for a day pass if you're not staying at HH). Go for seasonal "farm to spa" treatments such as the citrus ginger mani/pedi—with scrubs and potions made from locally sourced Meyer lemon, as well as a sublime hand and foot massage and perfect nail sculpting, this is one of the best nail treatments we've had yet. //25 Matheson St.,


The easily walkable Healdsburg square is lined with independent shops. Head to Bon Ton Studio(120 Matheson St.), a carefully curated boutique featuring classic wardrobe staples, woven fabrics and various decor. Its sister store, Bon Ton Baby, recently opened with the same aesthetic but for kids. Other choices for women’s apparel include festival-worthy attire at Gathered(322 Center St.), casual looks at Ooh La Luxe(326 Healdsburg Ave.) and quality trendy pieces at Punch (387 Healdsburg Ave.).

For other provisions, Ciao Bruto!(130 Plaza St.) is a newly open shop that sells Italian foods and biodynamic wines; Lucky Heron (333 Healdsburg Ave.) offers an eclectic assortment of creative gifts; and Jam Jar(126 North St.) features original art, handcrafted jewelry, and housewares.

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