Savor the fruits of picking season in Sonoma County’s out-of-the-way wonder.
Name-checked on countless Best Small Towns in America lists and endowed with a buxom selection of tasting rooms and boutiques, Healdsburg is a secret no more. Once a little-visited outlier on the Sonoma wine trail, the town now sits squarely on the wine-getaway A-list – propelled by a flurry of positive press coverage over the past decade.
Still, the thing I love best about the Sonoma County town is leaving it – or more precisely, hopping on a bike and gliding around the rolling, winery-encrusted foothills just a few miles up the road from all those boutiques, restaurants and galleries.
“Let me know if you want to slow down the pace,” the tour guide tells our small group, as we gear down and round a bend on leafy West Dry Creek Road. After my biking experiences in Napa – hotter, more congested and generally just hairier – this self-propelled wine tour is literally a breath of fresh air.
Founded by a Midwestern land-squatter in the years following the Gold Rush, Healdsburg resides about 30 miles north of Sonoma and Napa, but those 30 miles buys you a lot – less hubbub, shorter waits and a sleepier, more genteel vibe, even with the new notoriety. And for a town of 11,000, it boasts one of the densest hospitality biomes you’ll find in California, which explains all those best-small-town accolades.
The smallness is not so unusual. The confluence of art, wine, food and fitness is something else.
When to Visit
NorCal wine-country habitués know that September is the sweet spot for visits: cooler than mid-summer (average high: 87) and dry as a bone (average rainfall: 0.2 inches).
Staking a Claim
Pick your poison: You can get to Healdsburg via a visually majestic drive from San Francisco International Airport (94 minutes, over the Golden Gate Bridge) or a shorter, somewhat less exalting route from Oakland International Airport (82 minutes). Both routes meet up with the US-101 highway, which takes you right into the heart of town.
How to describe Healdsburg? It’s as if someone took Old Town Scottsdale and cross-pollinated it with a New England college town. It’s quaint and seasoned, but unmistakably upscale, with interesting flashes of adaptive reuse and modernism.
After brunching on a terrific Monte Cristo on house-made cinnamon-walnut bread at Costeaux French Bakery (costeaux.com) – an Oakville Grocery-esque culinary hybrid that will gladly box up a gourmet picnic lunch to take with you on one of your winery excursions – I backtrack a few blocks to h2hotel (h2hotel.com, $368/night), an eco-forward boutique hotel done in steel and glass, set right on the main thoroughfare. Some things I end up loving about h2hotel: the loaner bikes, one of which I borrow straightaway to tour a flat loop of old barns and vineyards located beyond Dry Creek just west of the hotel; Spoonbar, the hotel’s unpretentious night-side restaurant and watering hole, where I have an enormous, traffic-stopping pork chop served over polenta, and enjoy an edifying chat about American whiskeys with a convivial bartender; and my elegantly minimalist, pseudo-Japanese “eco-suite,” with its come-hither plunge tub and balcony views of Fitch Mountain in the distance. The 36-room property also has one of the flat-out coolest lobby lounges I’ve ever seen, dominated by glass walls, steel shelving filled with blown-glass bottles and vases, and calmingly kooky-patterned couches.
It’s all a bit like staying in a tech CEO’s wine-country mansion for the weekend.
Other promising options from among Healdsburg’s roughly 30 hotels and b&b’s are the antebellum-inspired River Belle Inn (riverbelleinn.com); the modernistic, Marriott-branded Hotel Trio Healdsburg (hoteltrio.com); and the luxe Hotel Healdsburg (hotelhealdsburg.com), which has a 60-foot swimming pool and offers cooking classes.
Hoofing it Downtown
Can’t decide whether to start your walking tour of downtown Healdsburg with a visit to an art gallery or a wine tasting? Cover both in one fell swoop at The Harris Gallery Art & Wine Collection (theharrisgallery.com), a singular marriage of two great Northern California traditions that will effortlessly eat up a half day of your visit.
Founded in the early 2000s by abstract painter M.C. Harris and his son, A3L3XZAND3R, the gallery is set in a gorgeous, turn-of-the-century stacked granite building with distinctive Italianate arches. It originally served as the town’s first bank. Today it houses Harris’ bold, colorist landscapes and subtly vaginal, O’Keeffe-ish floral canvases; and A3L3XZAND3R’s eerily ennobling scenes of windswept clouds and silent countrysides. Both artists’ work is democratically positioned throughout the gallery’s many offices, hallways and anterooms.
The gallery also has a pleasant outdoor lounge where you can sample the Harrises’ proprietary collection of austere, Burgundy-style wines. Favoring grapes from the Anderson Valley north of Healdsburg, where cool sea winds create an advantageously taxing climate for winegrowers, the Harris family turns the outsourced fruit over to winemakers Wells Guthrie and Leo Hansen, who create low-alcohol, naturalistic stunners like the 2020 Sterling Ranch Chenin Blanc, replete with honeydew and mineral notes. Each vintage includes wine-label art created by the Harris boys themselves, adding a fun second dimension for collectors or talking point for dinner parties.
My suggestion: Start with the tasting, then order a full glass and tour the gallery. Makes those cloudscapes and suggestive tulips even more engrossing.
The Harris Gallery is one of roughly two dozen fine art shops in Healdsburg, not counting the de facto artist exhibits you’ll find in its many tasting rooms. Sometimes the tasting room itself is the artwork, which is certainly the case at Marine Layer Wines (marinelayerwines.com) on Center Street, launched in 2021. Designed by local Sonoma design firm Hommeboys, the tasting room has a lounge-y, low-slung chicness that’s unmistakably Californian – if you’ve never sipped Chenin Blanc on a futon, here’s your chance – combined with magisterial steel tones and arches. Cool place, and the wines – sourced from various vineyards around the Sonoma Coast, including Marine Layer’s own estate vineyard in the Sebastopol Hills – are uniformly complex and balanced, including a tartly high-toned 2019 Lyra
Stepping out into the midday sunlight, you’ll find another 35 or so tasting rooms lined up on Center Street and nearby storefronts – and considering the Darwinistic dynamic at play here, it’s highly unlikely you’ll find a dud in the bunch.
Biking and Wining
If you’re like me, you enjoy standalone tasting rooms just fine – but they don’t compare to estate tastings, where you get the full sensual sweep of a working winery, from the orderly, eye-pleasing sight of trellised grapevines under a midday sun to the excitingly musty aroma of an actively fermenting punch-down pit.
And if that’s the case, you’re in luck, because the Dry Creek Valley foothills just west of town are very nearby, easily accessible and absolutely lousy with wineries. The best way to visit them is by bicycle – keeps the calorie surplus down and moderates consumption – so we pay a visit to Getaway Adventures & Wine Country Bike Tours (getawayadventures.com) near downtown to get geared up. Owner and one-time ski bum Randy Johnson caught the biking bug in the late 1990s after he blew out his knee on a black diamond run and needed a torsion-less exercise to build up his quads. Convalescing in Calistoga, he humored his visiting uncle – a big wine aficionado – by taking him on a bike tour of local wineries, where Johnson sipped and swirled for the first time, learning the fundamentals of wine tasting.
Evidently, the uncle was so impressed by the experience that he referred a business associate to his nephew. Johnson initially declined, but the man was insistent. “He said, ‘I’ve got my boss and some clients coming with me and they really want to do it,’” Johnson recalls. “Then he goes ‘I’d even be willing to pay you!’ and the business was born.”
Johnson’s combo bike shop and adventure outfitter will do simple bike rentals (starting at $60/day) or guided excursions (starting at $250/trip). Casting out on meandering, mostly shaded West Dry Creek Road, we bike approximately 3 miles to our first stop, Quivira Vineyards (quivirawine.com), an organic winery and farm set on a vast, spectacular property with its own steelhead trout stream. Given the warm microclimate in this part of the valley, Zinfandel and Rhône styles are favored at Quivira, and we let sips of each take the edge off our thirst.
Next up: another 2 miles down the road to the Yoakim Bridge, where we cross over the eponymous creek to Amista Vineyards (amistavineyards.com). Known for its sparkling wines, the winery has a comfortable patio with scenic views of its 20-acre vineyard and Mount St. Helena. It’s purpose-built for lunching, and we enjoy getting a tongues-on primer in the art of making bubbly while noshing on the winery’s excellent charcuterie board, much of it derived from the on-site farm and garden.
Mill Creek Vineyards & Winery (millcreekwinery.com) – with its mature landscaping and diverse wine selection – makes for a lovely, low-key denouement if you decide to backtrack over the bridge and take the same route back to town. Your other option: Go for broke and bike south to Comstock Wines (comstockwines.com), set in a jaw-droppingly handsome, farmhouse-style main building with perfectly manicured lawns and an enticingly well-groomed bocce pit. It’s wedding-pic fodder, for sure.
No point in denying it: Comstock also affords me the most rapturous culinary experience I’ve had at a winery, in the guise of chef Jude Affronti’s “Wine & [Grilled] Cheese Pairing.” Essentially, it’s his deconstructed take on four cheese-forward comfort classics – the croque monsieur, the tuna melt, the Philly cheesesteak, and the classic grilled cheese with tomato soup – done as a French Laundry-style tasting menu. “We needed a cheese plate, but I need to have fun,” Affronti says, as I dip toasted brioche filled with gooey Irish cheddar into a hot bowl of fresh tomato soup, paired with a slightly buttery Chardonnay.
As we saddle up on the bikes a few minutes later, I give silent thanks that Comstock lets its chef have fun. It’s one thing this once-under-the-radar wine town continues to manufacture with still-surprising gusto.
3 Healdsburgian Culinary Gems
Don’t leave town without trying them.
Journeyman Meat Co.: Pick up a stick of Parmesan porcini sausage to take back home at this beloved downtown salumeria… or crack it open for an on-the-spot nosh between wine tastings. journeymanmeat.com
Noble Folk Ice Cream and Pie Bar: The name says it all. Two dozen flavors of luxuriously high-butter-fat ice cream plus cookies, cupcakes and assorted pastries. thenoblefolk.com
The Rooftop at Harmon Guest House: Perched atop a boutique hotel, it’s the magic-hour place to be in Healdsburg, and arguably its most accomplished purveyor of high-end global gastropub fare, from Baja-style crispy fish tacos to a soft-shell crab BLT. harmonguesthouse.com