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We try not to play favoritesand with so many lovely towns in Napa Valley and Sonoma County, you certainly don’t need tohowever, Healdsburg holds a special place in our heart. It’s beyond charming, walkable and really hip. Local shops, cafes, restaurants and boutique hotels thrive. There’s tons of opportunity to get out into nature (beyond just wandering through the verdant vineyards. Though, you can totally do that.) Healdsburg also has a dynamic dining scene with some of the most highly anticipated openings in the area and stalwart establishments that continually win praise from diners, chefs and critics. And, of course, the reason (most) people come to this part of Northern California—the wine really is some of the best in the world. And it’s not just the final product that’s so exciting but also the way grapes are being grown using recycled rainwater and regenerative farming practices. All this to say that Healdsburg earns our love time and time again, and if you do even a handful of the awesome things on this list, it will easily win your affection too.

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Courtesy of Black Oak Coffee Roasters

1. GET CAFFEINATED AT BLACK OAK COFFEE ROASTERS

Whenever there’s a destination that cares a lot about food and wine, great coffee is rarely far behind. Black Oak Coffee Roasters makes frothy lattes and also does single origin pour overs for java purists. All the baristas are super friendly, and it's good for people watching while waiting for your cup of Joe.

Emma K Morris

2. TRY THE BAKED GOODS AT QUAIL & CONDOR

Walk a few minutes past the main drag and you’ll find Quail & Condor, a neighborhood bakery that specializes in both sweet and savory treats, from asparagus and halloumi danish to almond croissants. Whatever you order, it’s sure to be the carby goodness required before (or, we suppose, the morning after) wine tasting.

Courtesy of Healdsburg Ridge Open Space Preserve

3. HEAD TO HEALDSBURG RIDGE OPEN SPACE PRESERVE

A quick 10-minute drive north of town sits Healdsburg Ridge Open Space Preserve. Whether you’re in the mood for a leisurely stroll or want to hit one of the easy to moderate hiking trails, it’s a lovely place to take a break from gourmet endeavors and see nature up close.

Courtesy of Marine Layer Wines

4. DO A TASTING AT MARINE LAYER WINES

Have you ever walked in somewhere and it’s just so unmistakably cool? That’s exactly what it’s like to step inside Marine Layer Wines, the most Instagrammable tasting room in Healdsburg. The wine—complex, cool-climate Chardonnay and Pinot Noir made from grapes grown on the Sonoma Coast—is almost too easy to drink.

Courtesy of Flowers Vineyard & Winery

5. BOOK A GUIDED FLIGHT AT FLOWERS VINEYARD & WINERY

Continue the Chardonnay and Pinot Noir party at Flowers Vineyard & Winery. The outdoor tastings happen at private tables in the gorgeous gardens. It’s truly one of the prettiest spots to sip wine and sample seasonal bites in all of Healdsburg (and that’s saying a lot).

Mariah Harkey

6. WANDER AROUND DOWNTOWN

Healdsburg Plaza is a shopper, wine lover and food mecca with dozens of boutiques, tasting rooms and restaurants concentrated in just a few blocks. If you walk a few minutes further in any direction, there are many more small businesses to patronize, including some excellent art galleries that showcase local talent and a sprawling, multi-room antique store.

Courtesy of Forager

7. SHOP FOR HOMEWARES

Home goods in a town that’s known for wine? Oh yeah! Forager, a modern mercantile, sells unique treasures like hand-forged steel gardening tools and garlic gourd baskets handwoven in Zimbabwe. Be sure to stop by Lime Stone to pick up some pretty things to elevate your table such as placemats, flatware and platters.

Courtesy of Barndiva

8. HAVE LUNCH AT BARNDIVA

Barndiva has a long-standing reputation for gastronomic excellence. Everything on the menu is made with the freshest ingredients and truly delicious. Sitting outside in the sun-drenched pebbled courtyard, drinking a glass of local wine and watching the burbling fountain, you might forget you’re in Healdsburg and not some pastoral town in Provence.

Courtesy of Healdsburg Farmers' Market

9. CHECK OUT THE HEALDSBURG CERTIFIED FARMERS' MARKET

Founded in 1978 the Healdsburg Certified Farmers' Market takes over the West Plaza Parking Lot every Saturday. It’s a great way to see all the fruits and veggies that are in season. Besides fresh-picked produce, stock up on flowers, cheeses, honey, olive oil, bread, fresh eggs, wild-caught fish, grass-fed meat and yummy baked goods.

Courtesy of Truett Hurst

10. PLAN A PICNIC AT TRUETT HURST

After hitting the Healdsburg Certified Farmers' Market, bring your haul over to Truett Hurst, a holistic vineyard and farm nestled in the heart of the Dry Creek Valley. Grab a red chair by the creek, open up a bottle of jammy Zinfandel and watch the salmon swim upstream. Before leaving, go say hi to the goats.

Courtesy of Spa Montage

11. SPLURGE ON A SPA TREATMENT

What exactly does a wellness sanctuary look like in wine country? At Spa Montage Healdsburg, it’s a serene space that’s elevated above grapevines. True to its roots, services are inspired by the natural beauty that’s all around. That means body wraps with honey from nearby apiaries and signature massages featuring cold-decanted local olive oil.

Emma K Morris

12. SWING BY LITTLE SAINT

We say “swing by” Little Saint but, fair warning, it’s not a place that's easy to leave. That’s because this highly anticipated eatery and community hub does everything oh-so right—a tasty plant-focused fare, music, art and an uplifting atmosphere that makes patrons want to stick around well past when the plates are cleared.

Courtesy of Chalkboard

13. MAKE A DINNER RESERVATION AT CHALKBOARD

It's true that kitchens across Healdsburg have access to some of the best ingredients. But it's the chefs who make them shine in thoughtful ways. Diners at Chalkboard get to savor Sonoma-style small plates in a cozy indoor dining room or outdoor terrace. As to be expected, the wine list is stellar, too.

Courtesy of Rooftop 106

14. GRAB A COCKTAIL AT ROOF 106

Want to switch up your libations for the evening? Roof 106, the trendy and atmospheric open-air lounge above The Matheson, has creative cocktails like the Roof One-Oh-Spritz, a tantalizing combination of prosecco, rosé, Aperol and pomegranate. Don’t worry, there’s still plenty of vino on the menu if a night out in wine country without Chardonnay feels too sacrilegious.

Courtesy of Harmon Guest House

15. SLEEP IT OFF AT HARMON GUEST HOUSE

After a day filled with food, wine and fun, you’re bound to be at least a little tired. The perfect place to rest up and recharge? Located just steps from Healdsburg Plaza, Harmon Guest House is a stylish and contemporary boutique hotel with rooms that flaunt huge soaking tubs, snuggly robes and ultra-comfy beds.

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