Since entering the spotlight in the early 2000s, Healdsburg has become something of a Wine Country darling, with a sweet, walkable downtown surrounded by wineries whose vineyard views go for days.
At the confluence of three AVAs, Healdsburg’s wine cred is matched only by its culinary one. Just within the last year, both scenes have witnessed an influx of new energy from big names like celebrity chef Charlie Palmer, cult favorites like Marietta Cellars, and welcome new additions like the True West Film Center.
This weekend itinerary gives you a generous helping of what’s new alongside some of our tried-and-true Healdsburg favorites.
Friday Afternoon: Check in to Grape Leaf Inn
(Courtesy of @grapeleafinn)
Healdsburg has welcomed a slew of new stays in the last year, including the Ken Fulk-designed Cottages at Little Saint and quietly luxurious Duchamp Healdsburg. But if you find yourself missing that laid-back, old-school Wine Country vibe—the one that dominated Sonoma’s small towns before the bigger names got in on the game—you want the Grape Leaf Inn.
This sweet, historic bed and breakfast is just a five-minute walk from downtown but feels like it could be miles (and years) away. The thirteen rooms named for French grape varietals are unfussy in a country-chic sort of way, with toile wallpaper and wooden four-poster beds. There’s a gourmet hot breakfast daily, served either in the dining room, outside on the wrap-around porch, or directly to your room, and, like any B&B worth its salt, wine is a complimentary treat on arrival and in the early evening happy hours.
Owned and operated by the group Wilson Artisan Wineries, guests at the Grape Leaf get member pricing for tastings at any of their eleven wineries in Sonoma and Mendocino, including the OG Wilson Winery in Healdsburg’s Dry Creek Valley (see more below). If you’d rather try them without leaving the comfort of the hotel, arrange for a private tasting (or a three-course wine-paired dinner) in Grape Leaf’s Speakeasy, the door to which is hidden Scooby-Doo-style in the main lounge. The Victorian estate also has a small spa where massages are available with 48-hour advance booking and, unusual for a B&B, a pool for cooling off on hot days.
// 539 Johnson St. (Healdsburg), grapeleafinn.com
Friday Night: Dinner at Folia Bar & Kitchen
(Emma Kruch)
Just because you’re not staying at one of Healdsburg’s newest hotels doesn’t mean you can’t enjoy their perks. Appellation Healdsburg, the new boutique brand helmed by celebrity chef Charlie Palmer and a former Four Seasons exec., bills itself as Sonoma’s “culinary-first hotel,” and their signature restaurant Folia Bar & Kitchen is a showcase for Sonoma County flavors and ingredients.
The three-course dinner menu ($85/person) revolves around Folia’s open hearth wood grill, with individual main courses like roasted duck breast with candied citrus and Mary’s chicken with white asparagus and green garlic, or large-format two-person dishes like the fish of the day. Snacks including the warm crab louis dip or kampachi crudo are worth an add, while dessert hits some real notes of comfort with options like sticky toffee pudding, lemon meringue tart, and Basque cheesecake. After dinner, head upstairs to the stylish rooftop bar Andy’s Beeline for a nightcap.
// 101 Dovetail Ln. (Healdsburg), appellationhotels.com
Saturday Morning: Wine Tasting at Wilson Winery
(Courtesy of @wilsonofdrycreek)
After a leisurely breakfast at the Grape Leaf, hop in the car for a less-than-ten-minute drive to Dry Creek Valley on the outskirts of town. There, in a restored historic tin barn, the more than 30-year-old, family-owned Wilson Winery has earned a reputation for bold, fruit-driven reds. World-class zinfandels are Wilson’s bread and butter, each produced with fruit hailing from local vineyards of vastly different character, some on remote 2,400-foot hilltops, others on the loamy valley floor. The largely outdoor tasting room—which overlooks acres and acres of vines and is guarded by a 26-foot-tall coyote (a former Burning Man installation)—is open for daily estate tastings ($25/person, free for members), which include a flight of four single-vineyard-designate wines.
// 1960 Dry Creek Rd. (Healdsburg), wilsonwinery.com
Saturday Afternoon: Downtown Healdsburg
(Courtesy of @acornhealdsburg)
After visiting Wilson, ditch the car back at the Grape Leaf—you won’t need it again today—and walk the few blocks to Healdsburg’s downtown plaza. Healdsburg’s beating heart is surrounded by boutique shops like home goods purveyor Anthem, modern mercantile Forager, antiquary Aerena Galleries & Gardens, clothing store Bon Ton Studio, and two—yes, two!—indie bookstores, Levin & Co. and Copperfield’s—not to mention several art galleries.
There are several good lunch options around the square, too, including the buzzy plant-based restaurant, wine purveyor, and music venue Little Saint. New kid on the block Acorn Cafe has quickly become a local daytime favorite with excellent people watching from the generous front patio. In addition to brunch options like shakshuka and green eggs and ham served until 3pm, they’ve got a list of daytime hits including grain bowls, corned beef reubens, and fried chicken sandwiches. They also offer grab-and-go salads, sandwiches, and juices at the counter. // 124 Matheson St. (Healdsburg), acornhealdsburg.com
After lunch, head just a couple of doors down to one of Healdsburg’s newest tasting rooms. Marietta Cellars isn’t a new winery—they’ve been building a reputation for almost 50 years, especially for their iconic Old Vine Red blend. But up until late last year, the only way you could get Marietta was by the bottle. The new tasting room is a curated breath of fresh air helmed by the label’s second-generation winemaker/owner Scot Bilbro and designed by his wife, Lisa Steinkamp. The airy space is full of intentional selections like a pock-marked century-old wooden work table, cultural artifacts, and contemporary art (some by Steinkamp herself). Their two tasting options ($35/person) take place inside or out on the greenery-filled patio: the Single Vineyard Series, predominantly red wines produced from Marietta’s disparate vineyard sites, and the Etta Series, small-lot wines that are light, fresh, and constraint-free. // 250 Center St. (Healdsburg), mariettacellars.com
Saturday Evening: Dinner at Bistro Lagniappe + True West Film Center
(Courtesy of @bistro.lagniappe)
One of downtown Healdsburg’s newest additions, Lagniappe serves French-inspired farmhouse cuisine showcasing exceptionally fresh, regeneratively farmed, pasture-raised, and line-caught Sonoma County ingredients. Wood-firing is chef-owner Jacob Harth’s specialty, a technique he applies to everything from oysters and pork chops to the puffy flatbread served with the onion gratin with comté. Every meal is best begun with the rye brioche with cultured butter, and don’t skip the dramatically crowned pot pie if it’s available; Wagyu steak frites are also a fan favorite. Sunday evenings they do a supper prix-fixe meal with a three-course “choice of” family-style menu and 20 percent off the wine list. Cocktails are fairly simple but effective, good for quenching your thirst in the classic bistro-style restaurant or out on its covered patio. // 330 Healdsburg Ave. (Healdsburg), lagniappehealdsburg.com
After dinner, head directly across the street to Sonoma’s burgeoning champion of indie cinema, the True West Film Center. While you can find some of the movies topping the American film charts here (Ryan Gosling’s Project Hail Mary is on now, for example), what you really want to keep an eye out for are the international, independent, and hard-to-find films and documentaries they show in one of three small theaters with luxury seating or in the North Lounge, a more casual space with $10 tickets. True West also sponsors multiple film festivals throughout the year including the Film Festival of Love, a five-day event which will appear for the first time June 24-28. // 371 Healdsburg Ave. (Healdsburg), truewestfilmcenter.org
Sunday: Martha Stoumen + Quail & Condor
(Courtesy of @marthastoumen)
Before heading for home, why not squeeze in one final tasting? One of California’s most adored natural wineries, Martha Stoumen, recently opened its first tasting room just a few blocks from the Grape Leaf in downtown Healdsburg. The warm, friendly space with vintage accents is a nice fit for the playful 12-year-old label specializing in more esoteric Italian varietals. A six-wine flight ($40/person) features some of those they rarely get to share with the public, but if you already have a favorite like the chenin blanc and vermentino blend Out to the Meadow, get your fill with a single glass instead. // 325 Center St. (Healdsburg), marthastoumen.com
Like Martha Stoumen, Healdsburg’s favorite bakery Quail & Condor recently upgraded, going from a tiny space to a 3,650 square feet with plenty of room for seating and enough staff to significantly speed up its notoriously long lines. Order off the cafe menu for Turkish-inspired simit, veggie quiche, and a tuna sandwich made with poached albacore, but don’t miss sweet and savory pastries like kouign amann and parmesan onion biscuits, as well as the bakery’s many varieties of sourdough. // 44 Mill St., Unit J (Healdsburg), quailandcondor.com
