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An ultimate wine-country town tempts at every turn

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Ninety minutes north of San Francisco and tucked among a bounty of farms and vineyards in Sonoma County, Healdsburg has enjoyed a steady rise as a tourism hotspot where innovative concepts and creations are born. Expect sophisticated dining, world-class wine, and a relaxed pace in this community cherished by locals and visitors alike.

What to Do in Healdsburg

Bring your walking shoes, because Healdsburg is built for strolling. Start in Healdsburg Plaza, the heart of the town’s commercial district, peppered with unique shops, inviting tasting rooms, and culinary delights. There are plenty of spots for a picnic blanket in this upscale enclave, and the tree-lined plaza hosts a Tuesday night concert series in the summer. Numerous art galleries also dot downtown, and the Healdsburg Center for the Arts, a block from the plaza, hosts the annual Healdsburg Arts Festival, classes, rotating exhibitions, and works by local artists for sale.

The downtown Healdsburg Farmers’ Market (Tuesdays and Saturdays with seasonal variations) was founded in 1978 and hosts fun food-inspired events such as zucchini races and pumpkin-carving contests in addition to cooking demonstrations and live music.

Another option for picnic fixings in town is Oakville Grocery, with an ample wine and cheese selection in addition to brick-oven pizzas, salads, sandwiches and other treats. For fresh-air fun, hit the Healdsburg Ridge Open Space Preserve’s 155 acres of trails leading through an array of terrain. Take the All-The-Oaks Trail and save snack time for the Russian River Overlook. During the warmer summer months, you can rent kayaks from Russian River Adventures and River’s Edge Kayak & Canoe for a meandering river adventure. Put in at the Healdsburg Veterans Memorial Beach, and spend a relaxing day plunging into swimming holes, lounging on sand bars, and watching for wildlife.

Getaway Adventures Bike Tours and Wine Country Bikes, both based in Healdsburg, offer bike rentals and tours, which are a great way to explore local vineyards and the bucolic landscape. If a self-led bike tour is your preference, stop in between wine tastings at the Dry Creek General Store  for lunch provisions and other locally made goods and gifts. 

Where to Taste Wine in Healdsburg

At the convergence of three highly regarded Northern California appellations—Alexander Valley, Dry Creek Valley, and Russian River Valley—Healdsburg offers a plethora of in-town tasting rooms with award-winning vineyards spread over the surrounding hills.

Downtown Healdsburg has a wealth of tasting rooms, and it is a great way to sample a large variety of styles and vintages with minimal travel and time. Bacchus Landing features several local wineries, including Aldina Vineyards and 13th & Third in addition to bocce ball courts and an artisanal food market. Marine Layer Wines was founded in 2021 and specializes in single-vineyard Pinot Noir and Chardonnay from the Sonoma Coast. Also new on the scene is The Drink, where you can try wines from innovative wineries Leo Steen and Rootdown.

Getting outside of town, whether on your own or with a tour, visiting working vineyards offers the opportunity to dive into a particular winery’s history, methods, and operations. Popular stops include J Vineyards and Winery’s stylish tasting room, Ferrari-Carano Vineyards and Winery and its new outdoor tasting terrace, and Preston Farm & Winery, where a husband-and-wife team grows fruits and vegetables, raises chickens and sheep, and produces sourdough bread and olive oil.

Where to Eat in Healdsburg

Healdsburg’s food scene rivals its vibrant wine venues. Fuel up for the day at Flying Goat Coffee or Black Oak Coffee Roasters, and grab buttery baked goods from Quail and Condor  or Downtown Bakery & Creamery. For a memorable weekend brunch, make reservations at Barndiva, where the menu choices include crab Benedict and black truffle croque madame. 

For dinner, consider making reservations (well in advance) at three-Michelin-starred SingleThread. Since launching in 2016, the farm, inn, and restaurant’s 11-course “Japan-meets-Sonoma” tasting menu has been reason enough for a Healdsburg visit.

Other beloved stalwarts include Charlie Palmer’s Dry Creek Kitchen where there’s no corkage fee for Sonoma-grown wines; the inventive farm-to-table menu and seasonal cocktails at Spoonbar; the handmade pastas at Chalkboard; and the barbecued Tomales Bay oysters and charred octopus tacos from Willi’s Seafood & Raw Bar.

Newcomers are grabbing a share of the spotlight, too. Little Saint is a 10,000-square-foot restaurant and arts complex home to murals, film screenings, and a plant-based menu designed by the SingleThread team. Upstairs is The Lounge, which hosts live music on Thursday nights; past artists have included Langhorne Slim, Elvis Perkins, and Zac Solokow. The Matheson, opened in September 2021, features two distinct dining concepts—a downstairs dining room that serves a seafood-focused menu with a “wine wall” of 88 self-serve taps and a roof bar that makes for a more casual night out.

Close the culinary tour with a mandatory stop at Noble Folk Ice Cream and Pie Bar, which features inventive ice cream flavors alongside decadent pies, cupcakes, and other baked goods.                                       

Where to Stay in Healdsburg

Healdsburg offers a range of accommodations, from cozy inns to shiny new luxury resorts. Opened in 2001, Hotel Healdsburg and its signature restaurant (Dry Creek Kitchen) helped spark a culinary and tourism renaissance in town. Harmon Guest House and h2hotel are two sleek, modern properties with a commitment to sustainable practices. Hotel Les Mars, an upscale 16-room property, offers complimentary French breakfast and daily wine receptions, while the Healdsburg Inn on the Plaza is a Victorian-style bed-and-breakfast overlooking the town center.

For ultra-luxury wine country experiences, the Montage Healdsburg, set on 258 acres of vineyards and oak tree groves, opened in 2021 just north of town with a spa, pool, and three restaurants. The SingleThread Inn offers five rooms appointed with amenities and products from local artisans and purveyors, includes full-service breakfast, and guests are guaranteed dinner reservations at the highly coveted restaurant (open Thursday–Monday). The Madrona, housed in a renovated manor originally built in 1881, is a 24-room boutique hotel west of downtown that reopened as a new, modern concept in April 2022. The restaurant is captained by Jesse Mallgren, who earned the former concept a Michelin star every year for 13 consecutive years, and sources ingredients from the eight-acre property’s on-site garden.

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