Traveler’s Guide to Healdsburg Plaza

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  • on SEPTEMBER 21, 2021
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Courtesy of Healdsburg Chamber of Commerce and Visitors Bureau

While Healdsburg is arguably one of the top wine destinations in California, attracting visitors from all over the world thanks to its world-class Sonoma County wines, luxurious hotels, vibrant dining scene, and stunning setting, it still manages to maintain its charming, small-town vibe.

The historic Healdsburg Plaza – established in the 1850s by gold-seeking Ohio native Harmon Heald – is a vital touchpoint for visitors, with an immense concentration of top restaurants, wine experiences, lodging, and activities all within a few square blocks. In fact, you could spend several days exploring everything that the town of Healdsburg has to offer without ever leaving the central plaza area.

With so much to do and see, it’s easy to feel overwhelmed with options. So, we’ve created a helpful guide of our favorite hotels, restaurants, wineries, bars, and activities in this famous town square.

Where to Stay

Courtesy of Facebook: Camellia Inn

There are plenty of hotels to choose from in the heart of downtown Healdsburg. While they each offer something unique, they all have one key perk in common – being centrally located within walking distance of all that the Healdsburg Plaza has to offer.

For those wanting to stay close enough to shopping and dining, but far enough away from the bustle of downtown Healdsburg, the Camellia Inn is a perfect option. Located just two blocks from Healdsburg Plaza, this charming bed and breakfast features nine guest rooms, a sparkling swimming pool, and gorgeous grounds planted with 50 varieties of camellia plants, which guests are invited to explore during a self-guided garden tour. The hotel also shares spa privileges with sister inn The Grape Leaf, for guests wanting to unwind, Wine-Country-style.

Courtesy of Facebook: Bella Luna Inn

Built in 1909, the Bella Luna Inn is also a five-minute walk from the Healdsburg town square. Guests can enjoy the newly renovated guest suites and cottage, along with a long list of top amenities like complimentary parking and WiFi, a heated pool, walk-in spa showers, microfiber sheets, and lush gardens. Rather than a traditional breakfast, the hotel provides gift cards to use at the nearby, award-winning Costeaux French Bakery and Café.

If staying right on the town square is what you’re after, the Healdsburg Inn on the Plaza is where you’ll want to be. This historic property elegantly displays its past, featuring the exposed brick interior crafted by Italian stonemasons, and the original staircase, amidst contemporary touches. Facing the park, you will find wine tasting, Michelin-starred restaurants, shops, and more, quite literally at your feet the moment you walk out the door.

Ditto for Hotel Healdsburg, whose central location on the western edge of the Plaza belies the almost resort-like amenities, which include lush gardens, a pool, a luxurious spa, and meeting and event spaces. Hungry? You don’t have to venture away from the Hotel Healdsburg to eat well. Just grab a bite at Charlie Palmer’s Dry Creek Kitchen, which is conveniently located on-site.

France meets Sonoma Wine Country at Hotel Les Mars, the 16-room member of the Relais & Chateau family of hotels just a block from the Healdsburg town square. Here you will enjoy luxurious accommodations, premium amenities, European-style service, and perks like complimentary French breakfasts and daily wine and cheese receptions.

Where to Eat

Courtesy of Chalkboard

Downtown Healdsburg is a foodie’s dream, with spectacular restaurants dotting the square and every side street. From independent coffee shops and wine bars to artisanal markets and Michelin-starred fine dining, culinary delights abound.

For starters, breakfast treats at Quail and Condor are an absolute must. Stock up on some of the most heavenly breads, baked goods, and pastries you will ever have in your life, like the light-as-air morning bun filled with bright lemon verbena cream, or the vibrant pistachio croissant, filled with Sicilian pistachio paste and adorned with pistachio flour and gold.

Grab a table on the patio at Campo Fina, and enjoy American and Italian-inspired dishes like housemade soppressata, wood-fired pizzas, and melt-in-your-mouth skillet meatballs, in a laid-back, al-fresco setting. Or, explore the bounty of Sonoma and Mendocino counties at Barndiva, the seasonally-focused farm-to-table restaurant that also features a next door art gallery, event space, and garden.

Courtesy of Facebook: The Matheson

For true on-the-plaza dining, check out the brand-new and buzzworthy dining and drinking behemoth The Matheson. This ambitious concept, with well-known Healdsburg chef and icon Dustin Valette at the helm, offers modern Wine Country cuisine in an exciting dining space that includes a farm-driven restaurant, sushi bar, dining loft, and rooftop cocktail lounge overlooking the square.

Just off the Healdsburg Square is Chalkboard, a lively and casual restaurant focused on sourcing the best local ingredients from Sonoma farmers and ranchers for a daily-changing menu of handmade pastas, crudos, fresh seafood and salads, and thoughtfully-prepared meats.

Celebrating something special, or simply feeling like indulging your senses? Book a reservation at the three-Michelin-starred SingleThread for the culinary experience of a lifetime, delivered via an 11-course tasting menu customized to your preferences.

Still hungry? Stop by Journeyman Meat Co., founded by one of Sonoma’s most famous wine icons, Pete Seghesio, for some handcrafted salumi, sausages, and local wines.

Where to Drink

Banshee tasting room, Courtesy of Banshee Wines

You can’t go to Sonoma County without partaking in a tipple or two! While the region is known for world-class wines made from pinot noir, chardonnay, cabernet sauvignon, and more, there are also plenty of other options if a craft cocktail or an expertly-pulled espresso are more your speed.

Kick off a day of wine tasting at The Drink, starting with a cappuccino or espresso from their adorable custom coffee cart, then moving on to a tasting of wines from Rootdown Wine Cellars and Leo Steen Wines, also under the same roof.

Banshee Wines’ downtown tasting room feels more like you’re hanging out at your best friend’s house over some beautifully-produced Sonoma County wines than it does a classic winery tasting room. Embodying the true community vibe of the Healdsburg Plaza, Banshee is a must-visit for those seeking cool climate, Sonoma Coast pinot noir and chardonnay in a laid-back, urban Wine Country setting.

About a mile from Healdsburg Plaza, the recently-opened tasting collective Bacchus Landing is worth the walk. With a slogan like, “Taste the Day,” one can do just that with the curated group of boutique wineries on-site. Relax in one of five wine tasting rooms, out on the piazza, or on one of the bocce courts as you sip small-production wines made from a variety of different grapes that thrive in the region, and nosh on local artisanal bites.

Check out the pleasantly brooding vibe at Burdock for inventive cocktails made from small batch and artisanal spirits, exotic flavors, and unique ingredients. A selection of equally flavor-packed small bites pairs perfectly with the lineup of spirited beverage concoctions.

Rooftop terrace at Harmon Guest House, Courtesy of Harmon Guest House

Whether or not you’re a guest at the bright and contemporary Harmon Guest House, featuring installations from local artists like Alice Sutro at every turn, a visit to the hotel’s Rooftop terrace is a must. Sip delicious craft cocktails like the Spicy Mezcal Margarita or the vodka-based “Rooftop,” with mixed berries, mint, and lemon, and nibble on appetizers as you take in the gorgeous views of Fitch Mountain, Sonoma Hills, and Downtown Healdsburg.

Where to Explore

Courtesy of Relish Culinary Adventures

With your belly full and a pleasant glow from some local sips, it’s time to hit the shops and stops in and around the Plaza.

Got little ones waiting at home for you? Don’t even think of walking in the door without picking up something from Toy Chest, the Healdsburg Plaza toy shop that brings back memories of what toy stores used to be like. You will find plenty of options for kids of all ages, from educational gifts to games to unique oddities that will surely beat the overpriced souvenirs at the airport.

For wonderful gift ideas or simply to treat yourself after all of that wining and dining, stop in to Mr. Moon’s to explore the dizzying selection of curated gifts, cards, stationery, clothing, jewelry, décor, and bath and body items.

If all of that dining at Michelin-starred restaurants has you feeling inspired to roll up your sleeves and get a little hands-on in the kitchen, book an experience at Relish Culinary Adventures. This state-of-the-art culinary center in downtown Healdsburg offers a plethora of activities and classes, from Wine Country cuisine to ethnic specialties, classes for kids, foraging tours, and more.

Looking for a good book? Be sure to check out Levin & Company on Center Street. This family-owned and operated independent bookstore has been in business in Healdsburg for over 30 years. Bookworms could easily spend hours perusing the shop’s massive selection of fiction, children’s books, and even CDs.

Courtesy of Facebook: Healdsburg Farmer’s Market

Don’t forget the famous Healdsburg Farmer’s Market. Taking place every Saturday and Tuesday from April through the fall and winter months, this is an essential experience for any Healdsburg Plaza visit.

When you’re finally ready to relax and recharge, book a treatment at A Simple Touch, one of the longest serving spas in Healdsburg. A hot stone massage or Organic Natural Herbal Spa Facial is sure to leave you feeling refreshed and ready to take on another day of sipping and savoring your way through Sonoma.

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Devin Parr

Devin Parr is a San Diego-based freelance writer and consultant specializing in wine, travel and lifestyle. In addition to covering the global wine industry, she is the resident expert in Temecula Valley Southern California Wine Country, serving as the region’s ambassador on behalf of the Temecula Valley Winegrowers Association. She holds a certification in wine expertise from the Apicius International School of Hospitality in Florence, Italy, as well as the Wine and Spirit Education Trust (WSET) Diploma. In 2017, she was named one of Wine Enthusiast Magazine's Top 40 Under 40 Tastemakers. Follow her adventures at @thesocalwinegal and