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 to stay in is Healdsburg, which is experiencing a spate of openings and remodels as new, locally owned businesses move into spaces that have been left vacant for years (such as Bear Republic Brewing Co., which left in 2019, and Shed, which closed the doors on its iconic space in 2018).
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.
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 come with lounge-worthy reading nooks and petite outdoor 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 it is helping to restore the natural habitat at Foss Creek, which runs behind the property.
- 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. As if that weren’t enough, the property’s restaurant, Hazel Hill, overlooks an expanse of rolling hills ideal for enjoying dinner and drinks at sunset.
- 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.
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.
For lunch with a view, head to Roof 106, a rooftop bar and restaurant that’s part of the newly opened Matheson, 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 fresh Ahi Tataki with puffed rice and sesame snow. In the evenings, the downstairs space becomes a bustling fine dining restaurant, and the bar area includes a serve-yourself wine wall featuring 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 at Dry Creek General Store, a popular deli and market on Dry Creek Road, in between winetastings, 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.
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 (indeed, many of the 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.
One of the most anticipated additions to Healdsburg’s dining scene, Little Saint, from the SingleThread team, opened in what used to be the Shed building in April 2022. Perfect for a visit at any time of the day, this new multipurpose space includes a coffee shop, bar, vegan restaurant, market, and event space that hosts live music every Thursday. (A surprise concert by Phoebe Bridges was recently hosted here.) Highlights include its cocktail and mocktail menu (don’t skip the M.E.T. Gala mocktail, a refreshing, nonalcoholic, hibiscus concoction) and seasonal dip trio with crudités from the nearby Little Saint farm.
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 current mayor of Healdsburg.
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. To sample the area’s best vintages, it’s absolutely worth venturing out to the wineries for a tasting among the vines.
Start your day 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 Co 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 a upscale food and wine pairing or a casual, prepared picnic basket (both with wine, of course), it makes an excellent stop around lunch time.
Back in Healdsburg, continue winetasting at one of the 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 an added 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.
If you’re done with wine entirely, head over to the open-air Fogbelt Brewing Co., which opened in the summer of 2022 and 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.
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 backroads. 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 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.