This Small Town Is the Jewel of California Wine Country, With Some of the Best Restaurants and Resorts in the World

Here’s what you need to know to plan the perfect trip to Healdsburg, California.

Healdsburg could fairly be described as the jewel of California Wine Country. It’s a special highlight of Sonoma County, which was one of T+L’s 50 Best Places to Travel in 2021. “It’s a charming little town where you can eat incredible pastries on a park bench under redwoods in the morning, taste wine and spirits at the source, grab an organic burger or wood-fired pizza for lunch on a patio, detox with a shrub or tea tasting in the afternoon, and dine on three-Michelin–star cuisine at night before walking back to your hotel — all without getting in a car,” says Sonoma County denizen of 20 years and Healdsburg expert Lisa Mattson, author of “The Exes In My Glass: How I Refined My Taste in Men & Alcohol” and food and wine contributor for Wine Country Table.

It’s the only town in wine country that sits at the epicenter of three different wine regions — Russian River Valley, Dry Creek Valley, and Alexander Valley — each with unique climates and grape varietals, Mattson adds. The distinctive year-round destination with just over 11,000 residents is a true epicurean hot spot with an extremely charming town square, around which some of its best hotels, restaurants, and shops sit, not to mention approximately 40 tasting rooms. “The culinary scene has the kind of diversity you find in a big city, but it's all centered around this quaint town’s park-like plaza,” says Mattson, and includes “Valette, the poster child for what a local wine country restaurant should be.”

In the miles just beyond there are around 80 vineyards, including renowned labels Flowers, Jordan Winery, and Silver Oak. Beyond that, the natural beauty is spectacular and begs visitors to get outside to enjoy hiking, biking, and horseback riding. In Healdsburg, it truly seems there's something for every taste and type.

Related: The Best Wineries to Visit in Sonoma, According to an Expert

Best Hotels & Resorts

Montage Healdsburg

Eight minutes outside of town, this resort nestled among acres of grape vines epitomizes bucolic wine country from its beekeeping experiences and farm-fresh Hazel Hill restaurant to its sumptuous, textural rooms and suites with floor-to-ceiling windows for taking it all in. The five-star  Montage Healdsburg was ranked No. 10 in T+L’s World’s Best Resorts in California of 2023.

Harmon Guest House

There’s no better place to be for sunset than the rooftop of this hotel — named for Healdsburg’s founder — that Mattson calls “artistic and hip.” Its 39 rooms are spacious and the socially oriented property, which includes an outdoor swimming pool, is outfitted with locally sourced art and furniture.

H2 Hotel

“When a hip eco-hotel has one of the coolest bars in town and is located across the street from the other two best bars in town, you know you’re in the right place,” says Mattson of Spoonbar, the drinking and dining destination that spills onto the sidewalk and back green space of this 36-room boutique hotel studded with succulents under a wavy roof.

Hotel Healdsburg

Fantastically located at one corner of the central plaza, Hotel Healdsburg, opened in 2001, is “the grande dame of downtown, though it’s not very big,” says Mattson. It brought luxurious hospitality to the wine-focused town before it was so widely known, and its lobby lounge, Spirit Bar, is where visitors and locals gather for live music and drinks. (“The happy hour menu is one of the best-kept secrets in town,” says Mattson.) The 55 modern, minimalist rooms; sunny swimming pool, fleet of bicycles, and Chef Charlie Palmer's Dry Creek Kitchen feel so very Californian.

The Madrona Hotel

This 1881 estate was reimagined in 2022 by co-owner and interior designer Jay Jeffers in a whimsical palette of antiques mixed with luxurious, colorful quirk. Then The Madrona made Travel + Leisure’s lists of the Best New Hotels and the Readers’ Favorite Hotels in the World in 202. Mattson suggests guests of the 24 glamorous rooms and suites “up your day-drinking game with a Sunday afternoon on the porch of this restored Victorian. The caviar and chips appetizer isn’t bottomless, but you’ll wish it was.”

Best Things to Do

Taste wines at vineyards and tasting rooms.

“I always take out-of-town guests to these three wineries and they are blown away,” says Mattson of Jordan Winery, Silver Oak, and Flowers, all respected producers with beautiful grounds and first-class experiences. There are limitless places to taste vinos from Healdsburg, which include pinot noir, chardonnay, cabernet sauvignon, and zinfandel. Other highly recommended stops include Reeve, Hawkes, Amista, and right in the plaza, Marine Layer and Idlewild.

Take a hike.

With gorgeous weather practically year-round, not to mention redwoods, forests, and rivers, Healdsburg is a pristine place to enjoy being outside. The Healdsburg Ridge Open Space Preserve is beautiful for solo hiking and forest bathing. Some wineries offer guided experiences: Bella Winery has Hike the Hill tours led by a local naturalist and nutritionist; Jordan’s 1,200-acre preserve hosts vineyard hikes on occasion; and visitors can take a half-mile walk at Amista’s Morningsong Vineyard. Two wheels are another way to go, like with Getaway Adventures’ Healdsburg bike and wine tours.

Try a craft class.

Winemaking isn't the only “making” happening in Healdsburg. Visitors can try their hand at skills such as block printing, moss wall art, and Japanese sashiko mending. There’s even a 19th-century North American art form called punch needle that curious types can try at Crafted at Appellation, where classes led by local designers are paired with premium wine and legitimately delicious bites (Chef Charlie Palmer is Appellation’s co-founder, after all). It's a lot cooler than the sip-and-paint sessions of yore.

Practice yoga among grape vines.

Indoor yoga classes will never be the same after you’ve practiced downward dog and warrior amid vibrant green vineyards. Several properties, such as idyllic Bricoleur Vineyards with its Sunday Yoga in the Vineyards, offer classes in true wine-lovers’ paradise. Amista Vineyards’ one-hour session is even followed by a glass of estate-grown bubbly.

Stop by a pop-up for dinner.

Pop-up restaurants and dinners are always on the menu somewhere in this foodie town, and Mattson highly recommends two in particular. Le Dîner is Troubadour Bread & Bistro’s hot French-leaning nighttime spot. And Second Staff puts on pop-up dinners at Marine Layer Wines’ beyond-cool tasting room after hours. “The chefs serve up small plates with Michelin flair without pretentiousness,” says Mattson.

Best Restaurants

SingleThread

“The dining experience of a lifetime,” Mattson calls this three-Michelin–starred 52-seat restaurant that’s also a five-room luxury inn and regenerative farm. Husband-chef and wife-farmer duo Kyle and Katina Connaughton are culinary dynamos who create pure magic on every plate, more than justifying the lengthy waitlist for reservations.

The Matheson + Valette

“Everybody loves Dustin Valette, our local kid who became a top chef and returned home to share his talents,” says Mattson of The Matheson’s chef/owner who opened the two-in-one terroir-celebrating restaurant in 2021 as a follow-up to his perennial fave Valette, across the plaza. (There, “Dustin’s portions and hospitality are as generous as his personality,” says Mattson.) A micro-seasonal, hyper-local menu and 88 wines by the taste or glass are served downstairs and up top, Roof 106 is where Mattson says “fried sweet corn, marinated olives, and pork belly pizza are always on the hit list.”

Barndiva

“A vibe not to be missed,” is how Mattson describes one of her personal favorites for not only the Michelin-starred farm-to-fork cuisine in “a style that is fresh, modern, elevated, and distinctively Barndiva,” but also the garden atmosphere and non-alcoholic libations. The Belly Rub Shrub is made with a turmeric spirit, turmeric-beet shrub, and ginger.

Little Saint + Second Story

Healdsburg's hottest vegan eatery, Little Saint, features a “shrub bar and focus on low-alcohol and no-alc drinks [that] fills a void in our boozy bougie town,” says Mattson, who is especially excited about its new sister fine-dining restaurant upstairs, Second Story (also vegan). It opened in summer 2023 with Executive Chef Stu Stalker, wooed from Copenhagen’s world-famous Noma.

Bravas Bar de Tapas

This year-round indoor-outdoor local favorite is “our beloved tapas bar in an old Craftsman bungalow that serves sparkling wine in coupe glasses,” says Mattson. The chef/owners Mark and Terri Stark are James Beard finalists who have a particularly magical touch when it comes to authentic Spanish paella.

Best Time to Visit

The quintessential time to visit Healdsburg is May through August because of the weekly Tuesdays in the Plaza summer concert and picnic events and the Healdsburg Jazz Festival in June. Visitors, and there are many, can expect hot, dry days and cool nights — think temperature swings of 30 degrees. Mattson says her personal favorite times are the shoulder months of April and November, “when it’s a little less crowded.” That said, she also loves March — the end of late winter’s mustard season, when the wild yellow blooms cover fields — when spring is just making itself known and Chef Charlie Palmer hosts the two-day Pigs & Pinot extravaganza at Hotel Healdsburg. Barndiva’s Fête Blanc each August and Fête Rouge every November are fabulous parties, says Mattson, who also encourages foodies and oenophiles to visit in quiet, cool January and February. “So what if it’s raining? You’ll be inside a tasting room, tea house, distillery, coffee shop, cafe, or restaurant anyway.”

How to Get There

Healdsburg is a fairly scenic 75-minute, 70-mile drive from San Francisco and the Bay Area, though beware of end-of-week congestion as Northern Californians escape to wine country on weekends. From the rest of the country (or world), flying is the way to go. One option is landing at San Francisco International Airport (SFO) or Oakland International Airport (OAK), renting a car, and driving the 83 miles north — it's the same distance from both. Another is flying directly to Charles M. Schultz Sonoma County Airport (STS), a wonderful regional airport serviced by Alaska Airlines, American Airlines, and Avelo. It’s just 15 minutes and 10 miles south of Healdsburg and has a Hertz rental car outlet and Lyft, Uber, and taxi pickup areas.

How to Get Around

While Healdsburg is incredibly walkable, it would be a shame to not visit any wineries, which requires four wheels. Ride-shares are not reliable modes of transportation as there are not many drivers. “I’m not saying you can’t get lucky with ride-share, but you really need to plan ahead and be prepared to wait for a driver,” says Mattson. The safest route: Use your own rental car with a designated driver or book a tour guide or driver service, of which there are many in the area.

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