Sonoma County’s wine country has long been a favorite getaway destination for Bay Area residents and out-of-state visitors alike. With over 425 wineries and 18 AVAs, it’s a vast and varied viticultural area worthy of many weekends of exploration. Because the county is so spread out, which of its small towns you choose as your base—be it apple-loving Sebastopol, historic Sonoma, or riverside Guerneville—will determine how you spend your weekend.
Right now, one of the most exciting towns for a stay is Healdsburg, which is experiencing a spate of openings and remodels as new, locally owned businesses move in. This recent shift makes it easier than ever to spend an entire weekend (or longer) in the town center.
Even if you have been to Healdsburg before, go again. Though many old favorites remain, much is changing in this small NorCal town. Use this guide to navigate it all—from where to stay and things to do, to what to eat and drink in this corner of Sonoma wine country.
Where to stay
A stay in Sonoma County means moving a bit slower: long, leisurely breakfasts, predinner lounges by the pool, stargazing with a bottle of wine after sundown. All of our favorite places to stay in and around Healdsburg encourage you to take it easy and relax.
Each of the rooms at Harmon Guest House have multiple spaces for lounging—be it with a glass of wine or an espresso from its in-house Nespresso machines.
Courtesy of Bread & Butter PR agency
Harmon Guest House
- Book now: Harmon Guest House
Harmon Guest House is a peaceful yet centrally located retreat in the heart of Healdsburg. Each of its spacious, quiet rooms comes with lounge-worthy reading nooks and petite balconies, as well as large, comfortable beds that promise a great night’s rest. On site, guests are encouraged to spend time outside, be it at the hotel’s solar-thermal heated pool or the alfresco rooftop bar aptly named the Rooftop. Committed to sustainability, the hotel has also embarked on multiple ecofriendly initiatives, including the installation of a rainwater harvesting system. And the hotel is helping to restore the natural habitat at Foss Creek, which runs behind the property.
Montage Healdsburg
- Book now: Montage Healdsburg
The 258-acre property Montage Healdsburg officially opened its doors in 2020, becoming the first major resort property in the Healdsburg area. But in Montage’s case, large doesn’t mean obtrusive. It’s quite the opposite at this serene, nature-filled spot, which has seamlessly embedded itself into its surrounds with tree house–style rooms, each with a large outdoor deck, that sit perched above carefully preserved oaks. In addition, the property’s restaurant, Hazel Hill, overlooks an expanse of rolling hills ideal for enjoying dinner and drinks at sunset.
The Madrona
- Book now: The Madrona
The Madrona is a historic property, originally built in 1881 as a private residence but converted into an inn, Madrona Manor, in 1981. After a change in ownership in 2020 and months of extensive renovations, it emerged in its current form in April 2022 as an eclectic, 24-room boutique hotel and gathering place. With the help of designer Jay Jeffers, the space has been artfully transformed into a maximalist haven, all while preserving the soulfulness of the original structure. In addition to design changes, the property has added a resort-style pool and a bar and restaurant with a breezy patio where you’ll find guests and locals alike on warm evenings. Accommodations range from cozy guest rooms in the main mansion to private bungalows set in a flower-filled garden.
Read our full review of the Madrona.
The Lodge at Healdsburg
- Book now: The Lodge at Healdsburg
You have to love a wine country hotel where the reception area looks like a bar—and functions as one, too. Walking into the Tuscan-inspired Lodge at Healdsburg, you’re welcomed with a glass of local sparkling wine (or a local beer, if you prefer). It is a gesture that reassures you are indeed in the right spot. The 60-room boutique hotel was renovated and converted into a Hilton property—it’s part of the company’s Tapestry Collection—in 2023. The refreshed rooms are bright and sophisticated, with hardwood floors and gas fireplaces. Rooms look out on a central courtyard that feels very Tuscan, with olive trees and terra-cotta tiles (and two not-so-Italian hot tubs). During the spring and summer, the property is bursting with greenery. Bonus: The hotel is pet friendly.
The H2 hotel in Healdsburg features an eye-catching living roof that filters drain water and helps maintain the building’s climate.
Photo by Kim Carroll
H2 Hotel
- Book now: H2 Hotel
If you want to be right in the heart of Healdsburg, H2 is your spot. Even better: The 36-room hotel, opened in 2018, is an incredible example of sustainable (and gorgeous) architecture. H2 is LEED Gold–certified. The green roof is one of the property’s most noticeable features. But the hotel has a laundry list of other impressive features, including occupancy sensors that automate fans and AC, furniture made from salvaged lumber, and solar panels that heat the pool and the hot water in guest rooms. H2 is also impeccably designed. Rooms are bright and airy, with bamboo floors, live-edge tables, earthy but elegant colors, art from local artists, and glass carafes that you can fill from water stations on each floor. There’s plenty to do, too: Pick up a bike and tool around town; eat at the on-site restaurant, Spoonbar; or sign up for one of the hotel’s partner activities, such as a bike ride with pro cyclist Pete Stetina or gleaning (saving produce) with Farm to Pantry.
Where to eat
Start your day with coffee and breakfast at Black Oak Coffee in Healdsburg’s main square. Yes, the coffee is fresh, the staff friendly, and the food flavorful, but this colorful café is also community-minded. The team donates 10 percent of the sales from its house espresso to charity and regularly participates in local projects and fundraisers, such as supporting volunteers at the annual Russian River Watershed Cleanup.
Or head straight for Quail & Condor, a bakery from SingleThread alums Melissa Yanc and Sean McGaughey. The pair is lauded for their long-ferment croissants and handmade sourdough breads, but you can’t go wrong with any choice. On a recent visit, highlights included parmesan and onion biscuits, black sesame calamansi cake, and a to-die-for gluten-free cookie. Their merch game, such as a sweatshirt emblazoned with the phrase “weirdough,” is strong, too.
Second Story’s vegan tasting menu comes with delicious starters, including skewered roasted veggies.
Photo by Emily Dorio
For lunch with a view, head to Roof 106, a rooftop bar and restaurant that’s part of the Matheson restaurant, located in the building that used to house the now-shuttered Snowflake Bakery. Not coincidentally, Snowflake was founded by Honoré Valette, the great-grandfather of Matheson chef and owner, Dustin Valette, who wanted to keep the space a lively part of the Healdsburg community. While best known for its pizzas, you won’t want to miss the Asian chicken salad with shaved cabbage and togarashi puffs. In the evenings, the downstairs space becomes a bustling fine dining restaurant, and the bar area includes a serve-yourself wine wall with an incredible selection of vintages from around the world, including hard-to-find local and foreign wines, like Opus One from Napa.
If you’re on the go, grab a sandwich in between winetastings at Dry Creek General Store, a popular deli and market on Dry Creek Road, or stock up on picnic goods at Italian market Ciao Bruto before you head out for the day.
For a predinner cocktail, you can’t go wrong with the lively, garden-adjacent patio at the Madrona, or the sweeping sunset views at Hazel Hill. But if you don’t feel like venturing outside of the town center, hunker down at locally loved Lo & Behold for cocktails and fried chicken. All three have a full dinner menu (Hazel Hill’s set tasting menu is a real treat) and are excellent options if you’re hankering for more than just a bar bite.
Or head to Le Diner Troubadour, where one of Healdsburg’s best sandwich spots—owned by the team behind Quail & Condor—transforms into an intimate 20-seat bistro at night. The menu changes constantly with the season, and it’s always fantastic: Think mussels with onion and chervil, an herb salad with black sesame and cultured cream, pork with persimmon and nasturtium. The oat porridge sourdough (which you can also find at the bakery) is not to be missed, especially with the butter they make in house—chef’s kiss.
Try house-made pastas and wood-fired pizzas at the Wes Anderson–inspired Molti Amici.
Photo by Aislyn Greene
For something a little more casual, check out Molti Amici, an Italian spot with a very Wes Anderson vibe. From the gold lettering on the door, to the green-and-white-striped bench cushions, to the mirrored bar with a neon sign that says “many friends,” (or “molti amici”), the restaurant feels both elevated and inviting. The food does too: beet salad with labneh, house-made pastas like gnocchetti with spring peas, and excellent wood-fired pizzas (try the polpetta & pepperoni). Naturally, it has a bocce court in the back patio.
No list of places to eat in Healdsburg would be complete without a mention of SingleThread, a 52-seat restaurant with three Michelin stars that has garnered much critical acclaim since opening in 2016. Chef Kyle Connaughton, who studied in Japan, pairs ancient Japanese techniques with a hyper-local, farm-to-table mentality (many ingredients come from the farm he and his wife, Katina, operate) to create a sublime series of small bites. SingleThread also operates a luxurious five-room inn above the restaurant—book both for a truly decadent getaway. Dinner reservations open on the first of the month prior and sell out quickly.
Vegans (and honestly, nonvegans), take note: Little Saint, from the SingleThread team, opened in what used to be the Shed building in April 2022. Perfect for a visit any time of the day, this new multipurpose space includes a coffee shop, bar, market, and event space that hosts live music every Thursday. (Surprise concerts featuring notable names like Phoebe Bridgers are a common occurrence.) But the real treat is the tasting menu at Second Story, which is, yes, on the second floor of the building, with a lovely view of the town’s treetops. Settle in for the evening and watch a parade of vegan dishes appear: poached beets with marigold and hops, confit squash with chestnut, potato terrine with preserved truffle. The menu is always changing, but you’re guaranteed a creative and eye-opening experience.
End your night with a cup or cone at Noble Folk Ice Cream, a popular, LGBTQ+-friendly ice cream spot owned by Christian Sullberg and partner Ozzy Jimenez—who also happens to be the former mayor of Healdsburg.
The Setting Wines at Bacchus Landing offers snack boards and pizza as part of its tastings.
Photo by Aislyn Greene
Where to drink
Healdsburg is close to two main AVAs: Dry Creek, which is known for its zinfandels, and Russian River, best known for its pinot noirs and chardonnay. And it’s absolutely worth it to explore beyond the main town. But you could also spend an entire weekend tasting within the borders of Healdsburg. Start at Bacchus Landing, a new Tuscan-style complex with five different tasting rooms. Highlights include the Setting Wines, a collaboration among three friends that highlights some of the most prestigious vineyards in the region (it’s nearly impossible not to leave with a least one bottle of winemaker Jesse Katz’s cabernets), and Smith Story, run by a wife-and-husband team and highlighting vineyards in Sonoma and Mendocino counties. Make sure to say hi to winery pup Lord Sandwich. In the main Bacchus Landing courtyard, you can also find live music and a wood-fired pizza oven that keeps guests grounded—and full—between tastings.
The design at Marine Layer Wines’ tasting room is almost (almost) as delightful as its wines.
Photo by Jessie Beck
Continue winetasting at some of the other newer tasting rooms in town. With an indoor tasting room and patio, BloodRoot is a hip establishment pouring high-quality, affordable wines made from grapes sourced throughout Sonoma County. Although the somms won’t reveal where exactly (the secrecy is part of why they’re able to keep prices down), we promise: Their sourcers know how to pick a great grape. A few blocks away at Marine Layer, guests are treated to both a visual and olfactory experience while sampling wines sourced from the Sonoma coast. In its fresh and youthful tasting room, designed by L.A.-based firm Hommeboys, stylish patrons sip on delicately balanced, slightly saline pinot noirs while lounging in yellow velvet chairs. As a bonus, both are open until 7 p.m. (most tasting rooms close at 5 p.m.), making them ideal for an end-of-day glass of wine.
Also new to the scene are the Society and Maison Wine Bar. The Society features wines from the Foley Family portfolio of wineries in what feels almost like a posh wine club, with wood-paneled walls and a leather couch. Try one of its pairings, which range from caviar and bubbles to chocolate and wine. To truly nerd out, spend an evening at Maison Wine Bar. It’s a little hard to spot on the main drag, but once you’re in, owners and sommeliers Evan Hufford and Ryan Knowles can walk you through their favorite California wines, or even beer and sake. It’s both a wine bar (that’s open until 2 a.m.!) and a retail shop, plus they host semi-regular wine dinners in partnership with groups like Second Staff.
To venture beyond Healdsburg proper, start by exploring the Dry Creek AVA at Bella Vineyards, a family-owned and family-friendly winery on expansive property with rows of old vines and even older redwoods. While you could opt for a straightforward tasting on its olive-tree dotted lawn, we recommend trying one of the immersive tour options, such as its wine and hike option, or a truly unique tour of the vineyards in a decommissioned Swiss military car, which includes a stop for wine in a redwood grove. However, Bella is not the only one pairing wine with nature: Nearby Amista Vineyard and Sutro Wine also offer wine and hike tours.
For a sampling of Russian River Valley wine, make your way next to Bricoleur Vineyards. With the option to eschew a standard tasting for an upscale food and wine pairing or a casual, prepared picnic basket (with wine, of course), it is an excellent stop around lunch time.
If you’re done with wine entirely, head over to the open-air Fogbelt Brewing Co., which opened in the summer of 2022. It has been a much welcome addition to Healdsburg’s wine-heavy drinking scene.
Things to do—besides winetasting
Visit the Healdsburg Farmers’ Market and local farm stands
On Saturday and Tuesday mornings, don’t miss a stroll through the Healdsburg Farmers’ Market next to Foss Creek Parkway. Grab a coffee and a pastry, then wander around checking out the array of local produce and products, like artisanal mushroom jerky and deliciously fresh peaches that locals line up for.
If you’re not able to catch the farmers’ market, several farm stands, such as Preston Farm and Winery (open every day) and SingleThread Farm at Dry Creek (open Thursday–Monday) are great alternatives for a sampling of local produce.
As part of a Farm to Pantry volunteer shift, you’ll visit farms like this to help harvest produce that would otherwise go to waste.
Photo by Aislyn Greene
Learn how to make something—or how to glean
Appellation is one of the most interesting projects underway in Healdsburg right now. Helmed by local chef Charlie Palmer, it’s a series of new food-and-wine focused hotels, with the first opening in Healdsburg in mid-2025 (Petaluma, Sun Valley, and Pacific Grove will soon follow). The brand is all about celebrating the local bounty, so guest rooms will feature large, comfortable balconies, public spaces with retractable walls to allow the outdoors in during the spring and summer months, and a chef’s table in an orchard. In the meantime, the Appellation team has partnered with several local companies to run a series of classes (Crafted at Appellation) on everything from wreath-making—hosted at the Setting Wines in Bacchus Landing—to making cocktails or succulent terrariums.
Farm to Pantry is a local organization dedicated to gleaning—rescuing food that would otherwise go to waste. Founder Melita Love was on a walk when she noticed that fruit was rotting beneath her neighbor’s trees—so she debuted a solution. Now the team and volunteers (like you!) work with local farms, gardens, or really anyone who has a tree full of fruit to rescue that produce and send it to local food banks. In 2023 alone, they rescued more than 400,000 pounds of produce.
Join a kayaking or cycling tour
For a little adventure before your next glass of pinot noir, join a cycling tour at Russian River Adventures. Although it has been operating river trips for over 20 years, it recently added a relaxed, three-hour e-bike tour through vineyard- and forest-lined back roads. The electric bikes make pedaling a breeze, and Bluetooth-enabled radios in each helmet allow riders to hear details about each landmark they pass from experienced tour guide Bruce Kramer.
Also in Healdsburg, Getaway Adventures offers bike rentals (including e-bikes) as well as a selection of cycling, kayaking, and combination tours. For those who can’t decide, its pedal-paddle tour is an excellent way to get a taste of both. Highlights include a picnic lunch stop in a beautiful grove of redwoods between activities and, if you’re lucky, a chance to spot otters, egrets, and other native Russian River wildlife.
Spend a day swimming at a pool or on the river
A surprising rarity in Sonoma wine country, Francis Ford Coppola Winery has a pool adjacent to its tasting room that’s open to the public (for a fee; cabines start at $220 for four people). Open from June to October, visitors can rent a bungalow or pool chair (if you can score it) and while away an afternoon sipping rosé or piña coladas while splashing in Coppola’s sunny space. No luck on reservations? Head to Healdsburg Veterans Memorial Beach or Steelhead Beach for a more nature-filled, BYOB day of swimming in the Russian River.
How to get there
From the Bay Area, Healdsburg is best reached by car and is a 90-minute drive north of San Francisco. By public transportation, the SMART train runs from the Larkspur ferry terminal to Sonoma County Airport, which is a 15-minute taxi or car share ride away from downtown Healdsburg—though plans to extend the line to Healdsburg are in the works.
Sonoma County Airport (aka Charles M. Schulz Airport) is also the closest airport for anyone coming in from outside the Bay Area, and it has direct flights to and from Seattle, Portland, Los Angeles, Denver, Dallas, Palm Springs, and Las Vegas.
