Lined with hip cocktail joints, endless dining, and boutique shops and tasting rooms, Healdsburg perfectly blends small town charm with big city imbibing.
The Best Restaurants in Healdsburg
(Courtesy of SingleThread)
It didn't take long for SingleThread to make an impression. In 2018, the restaurant was awarded three Michelin Stars in just its second year of operation, making it the first Sonoma County restaurant to ever earn three stars. Come hungry: SingleThread serves up an exquisite and colorful, 11-course tasting menu—think, quail roulade and coal roasted beets—sourcing ingredients from their very own farm. Restaurant bookings are released on the first of every month at 9AM. There' also an inn on-site where you can order up an in-room dining experience featuring a multicourse Donabe Hot Pot Dinner. // 131 North St. (Healdsburg), singlethreadfarms.com
If you're looking for a special occasion spot (many a wedding have made this their reception locale of choice), this is your place. The atmosphere is elegant, rustic, and screams Wine Country, with local farm animal-themed artwork, antique fixtures, and a tree-covered gravel patio draped with lights, that's positively hopping on weekend nights. As for the food, it's fresh, sophisticated, and beyond tasty (if salmon is on the menu, no matter what the preparation, get it—they source this from the gods). If you can't swing dinner, opt for an epic brunch. // 231 Center St., barndiva.com
Dry Creek Kitchen
If you're traveling with out-of-town parents, Charlie Palmer's Dry Creek Kitchen, at Hotel Healdsburg, is guaranteed to please with an approachable, modern American menu and seasonal ingredients fresh from Sonoma County. Settle in for a five-course tasting with pairings, but don't miss the wine list: More than 500 Sonoma lables promise a comprehensive taste of the region. —Chloé Hennen // 317 Healdsburg Ave., hotelhealdsburg.com/dry-creek-kitchen
Let Moustache Baked Goods sway you back to the twee dessert with cheeky flavors (The Beekeeper: meyer lemon, honey, and lavender), outrageously thick frosting, and flavorful cake. We'll gladly proclaim it's the best cupcake in the Bay Area, plus owners Osvaldo "Ozzie" Jimenez and Christian Sullberg (two local boys who just get it) serve up Tartine's Coffee Manufactory to wash it all down. //381 Healdsburg Ave., moustachebakedgoods.com
Bravas Bar de Tapas
Boasting 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 also 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 (topped with golden onions and white truffle honey) for a savory-sweet dessert. // 420 Center St., starkrestaurants.com/bravas
Head to Campo Fina for blisteringly delicious pizzas and homey dishes such as The Old School in a Skillet (meatballs with tomato sauce, parmesan, and ciabatta) or Nonna's tomato-braised chicken. Their back patio is ideal for an al fresco dinner, but even better for a giant salad or panini lunch (try the Cali B.L.A.S.T.) and a game of bocce. // 330 Healdsburg Ave., campofina.com
Chalkboard's casual atmosphere and elegant service has flourished since opening in May 2013. Chef Shane McAnelly lets his creative juices flow throughout a menu of small plates impossible to choose from, like Dungeness crab tater tots, calamari a la plancha, or any of the housemade pastas (for $45, you can taste them all). Whatever you do, save room for The Candy Bar: perhaps the ultimate throwback dessert with dense layers of brownie and caramel, a tower of roasted milk chocolate cremeaux, and scoop of nougat ice cream with peanuts on top. // 29 North St., chalkboardhealdsburg.com
Noble Folk Ice Cream & Pie Bar
This sweet little shop on the square by the Moustache Baked Goods guys taps into the hipster in all of us peddling "heritage pies" (like their amazing chocolate maple walnut version), 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., thenoblefolk.com
The Brass Rabbit
Brought to you by the fine folks at Chalkboard and chef Shane McAnelly, Healdsburg's unofficial Pasta House occupies a tiny nook on the square and serves up heaps of carbs that you'll never regret, like the Spaghettini Cacio e Pepe or Black Truffle Chevoo Filled Scarpinocc. They have a small but mighty cocktail list (try the Always Sunny in California with amaro, Cocchi Americano, prosecco, soda) and even do weekend brunch with $15 bottomless mimosas. // 109 Plaza St., thebrassrabbithealdsburg.com
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., theparishcafe.com
Healdsburg's Best Wine Tasting
(Courtesy of Jordan Vineyard & Winery)
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 and run Arista Winery is a fantastic representation of this region's prowess, for they cut no corners when it comes to the quality of their wines. Make sure you check out their stunning new winery facility while you're there. We also love MacRostie Winery, not just for their pinot and chard, but their gorgeous digs and panoramic views of the Russian River Valley.
If you want to go beyond pinot and chardonnay, plan a visit to Jordan Vineyard & Winery, an ivy-clad chateau where you'll want to sign up for one of their food and wine experiences. Winery chef Todd Knoll grows his own produce right on Jordan's property and you can even visit his massive gardens and a pair of donkeys on The Estate Tour, an epic, three-hour adventure that traverses Jordan's 1,200-acre estate. If you're short on time, they've just rolled out new experiences in their remodeled dining room. Napa's famed Silver Oak Cellars recently opened its Sonoma counterpart, a shiny new winery in Healdsburg. The super-green, state-of-the-art winery is an architectural masterpiece, so you'll definitely want to book a tasting experience that includes a tour. Both Silver Oak and Jordan make something that's harder to come by: killer Sonoma County cabernet. The historic Seghesio Family Vineyards 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 and recently launched a new food and wine experience, the four-course Chef's Table. Sparkling wine lovers should head to J Vineyards, where the J Bubble Room hosts a multi-course, sit down lunch paired with still and sparkling wines.
Don't have a designated driver? Take a walking wine tour of the town's many tasting rooms around the square. We love Siduri for its pinots that span California and Oregon, Banshee Wines, which you'll leave with inspiration for a total living room redesign, and Cartograph, offering wine by flight, glass, bottle, or on tap. Whatever you choose, you really can't go wrong.
Where to Have Cocktails in Healdsburg
(Courtesy of Spoonbar)
Credit the Bay Area's market-driven craft cocktail movement to Spoonbar in the H2Hotel, where "farm-to-bar" cocktails adorned with locally-sourced edible flowers are reasonably priced at $12, like the Sleeping Beauty (huckleberry vodka, rosemary, lemon, grapefruit, and pickled blueberries). Come here on balmy evenings, when they open the retractable walls up to the sidewalk, and consider yourself warned: dishes like Dungeness Crab Ciopinno or the Smoked Gouda Smash Burger may convince you to cancel your other dinner reservation. // 219 Healdsburg Ave., spoonbar.com
Duke's Spirited Cocktails
Duke's is carrying on a long tradition of slinging drinks to Healdsburg residents in its location that dates back 1933. This place truly embodies a local watering hole and serves up original cocktails with locally-made spirits and home grown accoutrements, like 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). There's also Boozy Grape Juice (wine) and Barley Treats (beer), if you're not feeling very spirited, plus a food menu of pre-dinner bites, including poutine and corn dog pops. // 4113, 111 Plaza St., drinkatdukes.com
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—we're not totally sure what this entails, but it sounds cool—which can all be paired 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., thetasteoftea.com
Flying Goat Coffee
Third wavers, this is your haven for coffee as good as any found in SF's 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. // 324 and 419 Center St., flyinggoatcoffee.com
Where to Stay in Healdsburg
(Courtesy of Harmon Guest House)
Harmon Guest House
The same developers behind the eco-chic Hotel Healdsburg and H2Hotel—both of which are also worth checking into (literally)—opened the Harmon Guest House, named after the town's founder Harmon Heald, in 2018. A geometric and modern design masterpiece, Harmon truly escorts this small, humble town into the 21st century. A sustainability super star, the hotel has natural light abound and comes with a bevy of amenities: free three-hour cruiser rentals, solar-heated pool, complimentary Sunday Yoga, daily breakfast, plus the only publicly-accessible rooftop in town, complete with a fire pit, bar, and panoramic views. // Rooms state at $249; 227 Healdsburg Avenue, harmonguesthouse.com
Grape Leaf Inn
If you get the heebie-jeebies at hearing the words bed and breakfast, take a deep breath and open your mind to the Grape Leaf Inn, a sweet little B&B just a jasmine-scented, few-block walk from Healdsburg's town square. Built in 1900, this 12-bedroom Queen Anne stay features a sunny-chic morning room; a speakeasy bar serving craft cocktails (4 to 7pm); and luxurious king rooms with spa tubs, fireplaces, and flatscreen TVs. When it comes to breakfast, you get what you pay for (it's included in your stay), but the grounds are truly wonderful: Planted with ancient cedar, roses, herbs, wisteria, delphinium and more, the gardens are a perfect spot for canoodling with a glass of wine in the afternoon; the Grape Leaf offers complimentary tastings from local winery partners of Fridays. Rooms start at $265. —CH // 539 Johnson St., grapeleafinn.com
Spas & Shopping in Healdsburg
(Courtesy of Spa Hotel Healdsburg)
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, 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. —CH //25 Matheson St., hotelhealdsburg.com/spa
Bummed is an understatement to describe how we felt when we learned that the beloved SHED marketplace was closing at the end of 2018. But the easily-walkable Healdsburg square boasts plenty of other independently-owned shops toting everything from women's clothing—shop designer threads at Looking Glass, wine country casual vibes at Zizi, and festival-ready looks at Gathered—to chic accessories at Clutch or socially-conscious goods at One World Fair Trade.