Healdsburg is renowned as one of California’s premier wine destinations, drawing visitors globally with its exquisite Sonoma County wines, luxe accommodations, vibrant restaurant scene, and picturesque surroundings, all while preserving its quaint, small-town atmosphere.

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

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.

Built in 1909, the Bella Luna Inn is a five-minute walk from the Healdsburg town square. Guests can enjoy the 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, acclaimed restaurants, shops, and more, quite literally at your feet the moment you walk out the door.

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, enjoy luxurious accommodations, premium amenities, European-style service, and perks like complimentary French breakfasts and daily wine and cheese receptions.

Where to Eat

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.

Grab a table on the patio at the newly opened Molti Amici, in the former Campo Fino spot, and enjoy beautifully executed Californian and Italian-inspired dishes, like handmade pastas and wood-fired pizzas, in a laid-back 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.

For true on-the-plaza dining, check out the 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, dining loft, and rooftop cocktail lounge overlooking the square.

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 a 10-course tasting menu customized to your preferences including specific dietary restrictions. There’s a reason why it’s one of Sonoma’s best restaurants year-after-year.

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

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 wines in a laid-back, urban Wine Country setting.

About a mile from Healdsburg Plaza, the newish 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 seven 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.

Back in town, you don’t have to be a guest at the bright and contemporary Harmon Guest House to visit the hotel’s Rooftop terrace. Sip delicious craft cocktails like their Espresso Martini and nibble on small bites as you take in the gorgeous views of Fitch Mountain, Sonoma Hills, and Downtown Healdsburg.

Where to Explore

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. 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 independent bookstore has been in business in Healdsburg for over thirty years. Bookworms could easily spend hours perusing the shop’s massive selection of fiction, children’s books, and even CDs.

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 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.

Conclusion

Healdsburg offers an enchanting blend of small-town appeal and world-class experiences, making it a must-visit destination in Sonoma County. Whether sampling exquisite wines, savoring Michelin-starred cuisine, or just meandering around the historic Healdsburg Plaza, you can bet you’ll be charmed by this burgeoning destination.