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Healdsburg

Healdsburg
Sonoma County’s oasis of glamour

This flawless-at-every-turn town, at the north end of Sonoma County, was recently listed as the No. 2 “Best Small Town to Visit” in the U.S. by Smithsonian magazine. Indeed, Healdsburg is a pretty small town—with a population of a little over 11,000—but many of the names here have become pretty big. Take, for example, the lavish luxury lodgings like the Relais & Chateaux Hotel Les Mars, local celebrity chef Charlie Palmer’s Dry Creek Kitchen in the heralded Hotel Healdsburg, and Valette restaurant from local hero chef Dustin Valette.

Still, even with some relatively recent arrivals, like market SHED—a modern “Grange hall” for farmers—there are longtime favorites. Downtown Bakery & Creamery, for instance, has been a staple for savory breakfasts since the café opened in 1987, and still attracts a loyal following for its sumptuous sticky buns, jam pockets, donut muffins, and cheddar cheese and thyme scones. Another excellent breakfast option is Singletree Cafe, home to a $4.95 breakfast special of eggs, potatoes, and toast, and its lunch menu features a burger that Charlie Palmer has called the best anywhere.

It’s easy to spend an entire day just wandering the environs of Healdsburg Plaza, lined with dozens of tasting rooms, each with their own vibe. Check out the big-city chic Cartograph with wines on tap, the stylish funky Banshee with its record player spinning vinyl, and the groovy Thumbprint Cellars with for-sale artwork on nearly every inch of wall.

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Spotlight: Sonoma County

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Spanning more than one million acres from the Pacific Ocean to the rugged Coast Range, this slice of wine-country bliss defies typecasting. Yes, it's increasingly famous for its premium wines, sharing the pedestal with Napa Valley for luxury cult collectibles like the wait-list-only bottles from Kistler Vineyards, A. Rafanelli, and Cirq.

But in Sonoma County you’re just as likely to stumble across extraordinary wines being crafted out of a backyard setup. Take Forestville’s Joseph Swan, which has been around since 1967 and still serves its award-winning wines out of a tasting room that’s really an old wood-barrel barn. Intimacy abounds at Sonoma County wineries. Often, it will be the actual winemaker who’s filling your glass, with his or her faithful winery dog sitting nearby.

Start your explorations with a quick geography lesson. There’s the town of Sonoma, with its historic Sonoma Plaza. Then, there’s Sonoma Valley, referring to the area between Santa Rosa and the town of Sonoma (and known as the Valley of the Moon), featuring individual wine regions such as Kenwood and Glen Ellen. And the then there’s the entire region encompassing it all, officially known as Sonoma County.

In Sonoma County, it’s often the actual winemaker who’s filling your glass, with the faithful winery dog sitting nearby.

An easy hour’s drive north of San Francisco, the journey through Sonoma County begins in the historic town of Petaluma, with its classic stone buildings. You could zip straight up U.S. 101 to arrive at the county’s northernmost town, the poshly perfect Healdsburg, but that would be missing the essence of this nook-and-cranny wine region—like the towns of Sonoma, Sebastopol, Santa Rosa, and Guerneville. It’s all about slowing down here, mingling with winemakers and locals, and knowing that it doesn’t get much better than this.

When to visit? Until a few years ago, agriculture-rich Sonoma County was primarily a summertime destination. But now the towns buzz year-round, thanks in part to festivals like January’s month-long Olive Festival, spring’s winery open houses, and autumn’s harvest events. Or come during the holiday season and you can ring in the New Year at boisterous parties at the county’s restaurants, wineries, and storybook inns.

—Carey Sweet

Eric Wolfinger

Single Thread

Single Thread
A husband-and-wife team marry California product with Japanese technique in this sumptuous Healdsburg establishment

Sonoma County offers travelers an embarrassment of riches but until recently gourmands seeking a world-class dining experience often felt compelled to venture east to the Napa Valley or south to San Francisco. Thanks to Kyle and Katina Connaughton, those days are over. The husband-and-wife team—he’s the executive chef; she’s the head of culinary gardens and farm manager—opened Single Thread in late 2016, instantly transforming the local food scene with their exquisite take on farm-driven, Asian-inspired haute cuisine. The 52-seat restaurant, which also features an upscale five-room inn, is worthy of making a special trip to Healdsburg.

The evening begins on the rooftop garden, where snacks are served, beverages are poured, and the day’s stresses soon melt away. From this vantage point, just one block off Healdsburg Plaza, you can see where the farm is located—about 10 minutes away on the banks of the Russian River. You are then escorted to the downstairs dining room, a stylish space that provides foodies with a clear view into the kitchen and offers design aficionados a master class in understated elegance. From the hand-carved wooden spoons to the custom sake cups (you get to pick your own!) to the Zalto stemware, every detail oozes excellence.

And then the food begins to arrive. Single Thread features three 11-course tasting menus—vegetarian, pescatarian, and omnivore—and the Connaughtons’ love of Japanese culture shines throughout. The first course is a collection of intricately crafted single bites—hyper-local selections of impeccably plated vegetables and seafood. The bulk of the seasonal menu is constantly in flux but Dungeness crab, Mt. Lassen trout, Monterey Bay abalone, Sonoma Grains, and assorted treasures from the Connaughtons’ farm feature prominently. Every bite marries California product with Japanese technique, and the results are uniformly magnificent without being the slightest bit fussy.

Excellence comes at a cost, of course. Dinner will set you back $225 per person, exclusive of service, and head sommelier Evan Hufford’s two wine-pairing options go for $155 and $295. (The wine program features many local favorites, including some hard-to-find bottles, and is worth every penny.) You’ll want to book your reservations at least several weeks in advance of your visit; new seats are released on the first of each month.

For the full Single Thread experience, book one of the rooms upstairs ($700–$1,000 per night) where you’ll find the latest Teforia tea system, Matouk linens, heated floors, and a Japanese toilet that may startle you the first time you encounter it. You can help yourself to the goodies in the room, which include candies created in the restaurant below and even a bottle of Pliny the Elder, the acclaimed (and hard-to-find) double IPA brewed down the road in Santa Rosa. Best of all, your overnight stay includes a high-end breakfast that somehow manages to build on your dinner experience from the night before and will prompt you to plan a return visit.

John Godfrey

“Across Sonoma Mountain, wisps of sea fog are stealing. The afternoon sun smolders in the drowsy sky. I have everything to make me glad I am alive.”
Jack London
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Sonoma County Wines & Wineries

Sonoma County Wines & Wineries
Toasting the region’s star sips

Given Sonoma County’s broad range of soils and microclimates, a most amazing thing happens. Roughly 40 grape varieties thrive here. If there’s dirt, it seems, an ambitious grapevine will find a way to make its home in that nourishing bit of earth.

As a result, there are more than 400 wineries across 17 appellations in Sonoma County. While wine grapes may not grow on the rock cliffs that line the Pacific Coast of Bodega Bay, you will find superb Chardonnay, Viognier, and Pinot Noir at the chilly, fog-enshrouded Peay Vineyards estate just four miles from the ocean. You can taste wines surfside too, at Gourmet au Bay overlooking Bodega Bay, with flights of boutique wines served on a little wooden surfboard.

In any tasting-based travels around Sonoma County, you’ll quickly encounter the Wine Road. It’s not actually a road in the sense of a single, continuous stretch of highway, but rather an association of wineries, which dates back to 1976 and now boasts nearly 200 wineries nestled among the Alexander, Dry Creek, and Russian River Valleys.

The Dry Creek Valley climate is Mediterranean, characterized by hot, dry summers with cool nights.

While Dry Creek Valley is home to more than 30 grape varieties, it’s best known for its Zinfandels, the black-skinned grape that brings hints of big brambly blackberry, blueberry, tobacco, and cracked black pepper. The climate here is Mediterranean—hot, dry summers with cool nights—which is a lot like the Italian peninsula. As a result, the local winemakers have taken a cue from the area’s early Italian settlers by using sustainable, organic, and biodynamic grape-growing methods, all similar to what those pioneers once used. You can taste the results at Papapietro Perry Winery’s tasting room and winery in Healdsburg, whose grapes are sourced from several nearby vineyards in Sonoma County.

For a taste of the famed Russian River Valley, go to the MacRostie Winery and Vineyards, which salutes owner Steve MacRostie, a legend for his superb wines from his original Wildcat Mountain Vineyard in the Petaluma Gap region of the Sonoma Coast. This estate winery and tasting room is set on a Healdsburg hillside and channels Sonoma County’s luxurious side with its polished oak tree trunk stools, leather chairs, and spaceship-globe chandeliers.

Alexander Valley is another must-visit spot, home to the 1,200-acre Jordan Vineyard & Winery. The stone and stucco castle focuses on Cabernet Sauvignon and Chardonnay, served with small bites from estate chef Todd Knoll and showcasing the property’s culinary garden.

Indeed, a lot of good Sonoma wineries make food a prime part of the wine tasting experience. In Sonoma Valley, Hamel Family Wines impresses with sophisticated small bites and cave tours, while St. Francis Winery offers a sumptuous multicourse small-plate lunch with guided wine pairings. And the Palate Play immersion at Ram’s Gate in Carneros-Sonoma is nearly a full meal, beginning with a backstage tour of the Howard Backen–designed winery and followed by a seated, guided pairing of wines and dishes.

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Sonoma County Luxury Lodgings

Sonoma County Luxury Lodgings
From luxury resorts to B&Bs, beautiful places to relax between tastings

With its varying array of landscapes, Sonoma County offers lodgings that range from luxury resorts to quaint B&Bs, all framed by spectacular surroundings. Consider Madrona Manor in Healdsburg, which is a historic 1881 Victorian mansion modernized with plush suites, Michelin-starred dinners, and extravagant service—all befitting its setting on eight acres of English gardens and wooded hillside. Take your gourmet buffet breakfast in the estate parlor, if you can bear to leave your room outfitted with antiques, pillow-top mattresses, and feather-soft linens.

Or perhaps the ocean is calling, in which case Bodega Bay Lodge beckons as the only AAA Four Diamond hotel on the Sonoma Coast. The seaside perch offers a luxury escape, in rooms snug with fireplaces, down comforters, and private balconies for stargazing. But plan time to dine too, at the resort’s Drakes Sonoma Coast Cuisine (the seafood on the menu comes from the same ocean glittering outside the windows). Or indulge in a sea-inspired spa treatment like the massage using warm tiger clam seashells.

Other notable retreats include the Fairmont Sonoma Mission Inn & Spa, with its 40,000-square-foot spa built atop a natural underground hot spring. Forestville’s Farmhouse Inn and Restaurant, meanwhile, offers a ravishing mix of gorgeous guest rooms and a Michelin-starred restaurant fed by farm-fresh food. Its seasonally inspired spa uses massage oils enriched by herbs and even heirloom apples grown right at the inn.

The spa treatments at Forestville’s Farmhouse Inn use herbs and heirloom cider apples grown right at the resort.

If a quaint, historic B&B or private bungalow is more your style, you’ll find joy amid the vineyards at spots like the Raford Inn, an 1880 Victorian plantation where breakfast brings stuffed French toast soufflé, and evenings glide in with complimentary wine tastings from neighboring wineries. For help-yourself luxury, the Victorian Auberge on the Vineyard offers a butler’s pantry stocked with complimentary drinks and baked goodies. At the Landmark Vineyards Cottage in Kenwood, you can choose between the two private cottages built on the edge of the vines, but happily they both overlook an award-winning winery estate in the foothills of the Mayacamas Mountains.

Since 1989, wine grapes have been Sonoma County’s top economic crop, replacing dairy, grain, and fruit.
Sonoma County Annual Events
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Sonoma County Annual Events

Sonoma County Annual Events
Mark your calendar for festivals, fun, and even grape-stomping

Every weekend, it seems, there’s another terrific festival or flat-out party going on in Sonoma County. One of the best comes in March, when Petaluma hosts California’s Artisan Cheese Festival, featuring farm and creamery tours, hands-on lessons in cheesemaking, and tastings of local cheese, wine, beer, and cider.

In May, you can feed your appetite for art with open studio tours during the annual Salmon Creek ArtWalk in Bodega Bay. And in June, the annual Days of Wine and Lavender, at Matanzas Creek, invites you to experience the fragrant plants in full bloom across the 100-acre Bennett Valley estate, with lavender-scented spa and culinary products available for purchase and chefs cooking up lavender-infused dishes for you to sample.

Sonoma County locals don’t require that all of their festivals be so fancy, though. They celebrate local fruit at August’s Gravenstein Apple Fair with tractor rides and pie eating, and rock out at September’s Russian River Jazz & Blues Festival, held at Johnson's Beach in Guerneville.

All year long, different Sonoma County wine regions hold open houses, such as April’s Passport to Dry Creek Valley, and Taste Alexander Valley in May. For the crown jewel, visit over Labor Day weekend for Sonoma Wine Country Weekend, when thousands of guests join chefs, wineries, and artisan food purveyors for three full days of wine tastings, elaborate meals, and the Sonoma Harvest Wine Auction.

Harvest time is one of the best times to visit a winery, to embrace the energy of sorting, stemming, and wine-crafting.

Still, harvest season is one of the best times to visit Sonoma County, when you can embrace the energy of sorting, stemming, and wine-crafting—and sometimes even participate in grape stomps. During this time of year, workers converge on the vineyards from dawn to dusk in late summer and early fall. For many wineries, the work actually runs around the clock, with innovators like Jordan Winery in Healdsburg picking fruit through the chilly nights. After all, keeping grapes cold protects their delicate flavors, as well as the pristine skin and pulp.

Some wineries celebrate the season by hosting pre- or post-crush parties with wine tasting, food, and live music. The Dry Creek Valley region hosts a slew of classy tastings and events, such as the Wine and Food Affair, when more than 100 wineries pair special wines with dishes they prepare and serve on-site. To really dive in, Sonoma Valley Crush invites guests to get hands-on over a September weekend at 15 area wineries, with one-of-a-kind, behind-the-scenes looks at every aspect of winemaking, from picking grapes and juicing to fermentation.

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Special Tours & Tastings Around Sonoma County

Special Tours & Tastings Around Sonoma County
How to give your wine country vacation an active flavor

Tour companies abound in Sonoma County, which are great for helping you visit a variety of wineries, with knowledgeable guides at the wheel who can pepper your journey with insights and fun tidbits.

Yet Sonoma County encompasses such a broad range of terrains that the mode for exploration happily goes beyond a mere shuttle or even a limo. You can go horseback riding, for instance, at Chalk Hill Winery or along the coastal bluffs of Bodega Bay at Chanslor Ranch. For more speed, go zip-lining through the redwoods with Sonoma Canopy Tours, hiking or biking with Getaway Adventures or Sonoma Valley Bike Tours, or kayaking along the Russian River.

Plenty of folks, of course, would rather just explore on their own. The free Sonoma County Vineyard Adventures program offers no-appointment, self-guided vineyard tours at top wineries (check its site for options, then pick up maps at participating wineries). Options include Matanzas Creek Winery, with its blooming lavender fields, or the 156-acre Paradise Ridge Winery and its stunning sculpture gardens. Happily, the strolls typically end at a tasting room, where you can toast your enhanced appreciation of the great outdoors.

California’s first commercial winery, Buena Vista, was founded in Sonoma in 1857 by Agoston Haraszthy, a Hungarian count.
Courtesy of Jack London State Historic Park

Sonoma County State & City Parks

Sonoma County State & City Parks
Embrace Mother Nature in wine country

Romp hand-in-hand on the beach. Stroll across grassy meadows. Savor a picnic in a mountaintop forest. Such fantasies can easily become reality in Sonoma County. An oasis stretching from the gorgeous Mayacamas mountain range to the Pacific Ocean, the region boasts so many parks, preserves, beaches, and vast open agricultural areas that you’re never more than a few minutes away from another outdoor adventure.

Salt Point State Park, for instance, features a marine conservation area and 20 miles of hiking trails along the rugged coastline, making it a prime spot to watch gray and blue whales. Grab a perch at Ocean Overlook to see the gentle giants traveling south to Baja California in January, heading from the Chukchi Sea near Alaska—then watch them travel back north in April or May for the summer feeding season.

Head inland to Glen Ellen’s Jack London State Historic Park, and you’ll see history, romance, and nature intermingle so harmoniously that it’s no surprise the famous author called the area his Beauty Ranch. Hikers and horseback riders share the 26 miles of trails to see a 2,000-year-old redwood tree and the centuries-old terraced gardens (the old-style version of sustainable farming). Don’t miss the ruins of the huge Wolf House that the London family had built, but which burned down before they could ever move in.

Annadel State Park in Santa Rosa offers more than 40 miles of trails for walking, biking, or horseback riding.

Even Sonoma County’s largest city, Santa Rosa (with fewer than 200,000 residents), is anchored by an enormous park. Annadel State Park spreads out over more than 5,500 acres of rolling hills, lakes, streams, meadows, and woodland. Hikers, equestrians, mountain bicyclists, and runners are all drawn here for more than 40 miles of trails. Keep your eyes peeled for a sight of the rare California red-legged frogs, popularized in Mark Twain’s short story “The Celebrated Jumping Frog of Calaveras County.” In Guerneville, you can hike the trails at Armstrong Redwoods State Natural Reserve, home to a grove of majestic coast redwoods—including one tree that is taller than a football field is long.

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Family-Friendly Sonoma County

Family-Friendly Sonoma County
From kid-friendly wineries to canoe trips and Snoopy sightings

This relaxed stretch of California wine country can be a surprisingly family-friendly getaway. For starters, a number of wineries, including the sprawling Francis Ford Coppola near Geyserville and Bella Vineyards and Wine Caves in Healdsburg, not only welcome kids but offer fun activities for the smaller set.

Sonoma Valley’s family-friendly attractions go well beyond wineries, too. Grab a few paddles at Burke’s Canoes in Guerneville for a day trip down the Russian River, with redwood-shaded picnic spots along the banks. Smaller kids, or grown-up train fanatics, love Sonoma TrainTown Railroad, a 10-acre park with quarter-scale replicas of classic locomotives and train cars. A 20-minute ride on the train travels through tunnels and over bridges and finishes near the park’s petting zoo and six carnival rides.

Other kid favorites include General Vallejo’s 1836 working ranch at Petaluma Adobe State Historic Park, where special events include special sheep-shearing days and living history performances about pre–Gold Rush California. (Check the park’s schedule for details.)

In Santa Rosa—which was the longtime home of celebrated Peanuts cartoonist Charles Schulz—let the kids clamber onto statues of Snoopy and his pals on the grounds of the Charles M. Schulz Museum. Inside, kids (and grownups) can enjoy thousands of original sketches and cartoon strips, sign up for special lessons on how to draw cartoon characters, or watch screenings of 1965’s A Charlie Brown Christmas and other Peanuts classics in the museum’s theater. Afterward, strap on some skates and take a spin at the adjacent Snoopy’s Home Ice, a Swiss chalet–style ice rink (be sure to have a cocoa at the rink’s Warm Puppy Café).

Also in Santa Rosa, consider a visit to the Luther Burbank Home & Gardens, where kids can smell roses, learn about growing vegetables, and look for birds in the famed horticulturist’s one-acre homestead.

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Petaluma

Petaluma
Sonoma County’s gateway to wine country and the Pacific Ocean

If you’re wine tasting in central Sonoma County, you’ll likely hear the phrase “Petaluma Gap” at some point. It’s a curious term, since there are only a few wineries in Petaluma—like Keller Estate and Kastania Vineyards—but the unique geographic region here gives many surrounding vineyards a famous, distinctive character. The 15-mile-wide "gap" flows from the ocean between Tomales Bay and Bodega Bay, through the coastal range mountains, then blows into San Francisco Bay—delivering wind, fog, and soil enrichment to the local grapevines.

As a town, Petaluma was built on its own river, which made it easy to deliver goods, like its world-famous eggs and chickens, to Oakland and San Francisco. Today, it’s still known for world-class food, like Cowgirl Creamery cheese, McEvoy Ranch olive oil, and both ROCKY the Free Range Chicken and ROSIE the Original Organic Chicken (both from Petaluma Poultry, founded in 1969 and still immensely popular).

No wonder Michelin has given so many nods to Petaluma restaurants—like Central Market, Cucina Paradiso, Luma, and Risibisi. Locally produced ingredients star on plenty of restaurant plates around town, like the roasted chicken, avocado, mozzarella, and mixed greens on hearth-baked pain de campagne at the beloved Della Fattoria’s artisan bakery. Or try the buttermilk fried chicken and roasted beet hash at Bistro 100, where all ingredients, including beer and wine, come from within 100 miles of the eatery.

Nightlife is another hallmark in this stretch of normally sleepy wine country, at top-rated micro-brewpubs such as Lagunitas Brewing Company, or the historic McNear's Mystic Theatre, famous for its live music. But first, spend a day shopping at the top-notch antiques stores lining Petaluma Boulevard.

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Downtown Sonoma

Downtown Sonoma
The historic heart of Sonoma County

In the mid-1800s, the town now known as Sonoma was just a collection of ranchos, governed by Mexico. Even though the U.S. government and the State of California took over the territory not too long after that, you can still sense its heritage. The centerpiece of town, Sonoma Plaza , is still anchored by the northernmost Franciscan mission in California—and it’s even the birthplace of the California State Bear Flag, created by Americans rebelling against Mexican rule. Today, however, Sonoma Plaza is lined with charming shops, tasting rooms, and popular restaurants.

To get better acquainted, take one of the cool historic tours of still-standing monuments. For starters, explore the parish-turned-museum Mission San Francisco Solano de Sonoma, the Sonoma Barracks military post and cannon arsenal, and the former home of Lieutenant Colonel Mariano Guadalupe Vallejo, commander general of the Northern Alta California's frontier forces and founder of the town of Sonoma.

You can get a Sonoma history lesson while wine-tasting at Three Sticks at the Adobe, set inside a historic 1842 home.

You can also find a history lesson at the tasting room of Three Sticks Wines at The Adobe: It’s actually set inside the historic 1842 Vallejo-Casteñada Adobe home, and features artifacts like an 1800s horse stirrup, delicate china, and tools. The nearby Pangloss Cellars Tasting Lounge, meanwhile, revels in a historic stone property built over a century ago, offering wine flights paired with bites like caviar, Cowgirl Creamery crème fraîche, and capers on crackers. And don’t miss Bartholomew Memorial Park nearby, home to Bartholomew Park Winery: Its on-site museum details the long history of Sonoma winemaking since the park’s first villa was built in 1861, and features a display of primitive agricultural tools.

For a wine-infused dinner, go to classic spots like B&V Whiskey Bar & Grille, which creates delights like an American Kobe brisket that’s been smoked over French oak barrel wine staves for 12 hours. For more contemporary fare, check out OSO, offering eclectic dishes like pickled shrimp tossed with kale-spiced peanut slaw and tomato-horseradish aioli.

Sometimes tasting pairs well with shopping too. Highway 12 Vineyards & Winery is tucked inside a home-accessories boutique, so you can sample Carneros Chardonnay while browsing hand-stitched stuffed toy dogs and embellished picture frames.

The eight-acre Sonoma Plaza, built in 1835, remains the largest plaza of its kind in California.
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Sebastopol

Sebastopol
This former hippie town has serious wine and food credentials

Once considered just a “hippie” town, Sebastopol is now arguably the arts and creative center of West Sonoma County. Its hotspot these days is The Barlow, a $23.8 million culinary, wine, and arts center that spans 12.5 beautifully landscaped acres. You can explore its wine tasting rooms, craft breweries, art galleries, and even fashionable, garage-style restaurants. But Sebastopol still has its earnest hippie soul, so banish any thoughts of chains: All tenants must be locals, making their own products. It’s so producer-driven that even much of the landscaping is edible, used in the restaurants’ food and cocktails.

This is still a small town too, with a downtown area a few blocks long and a scattering of outlying antique, ranch, and clothing stores where all the owners (and most of the customers) are straight from the neighborhood. Residents are fiercely proud of their offbeat and intimate burg, evidenced by spots like the tie-dyes of Cali Kind Clothing Co. and the wondrous insect-eating plants found at the California Carnivores nursery (those hungry flowers add flair and function to any home).

A day of wine tasting in Sebastopol is like a celebrity tour, sampling the works of big-name but tiny-production vintners.

Otherwise, small-production wineries and vineyards sit amid the maritime-fog-enveloped hillsides here, like Kosta Browne, Iron Horse, Dutton, and Cirq. A day of tasting is like a celebrity tour, sampling the works of big-name but tiny-production vintners such as Paul Hobbs, Merry Edwards, and O’Connell (the latter the winner of the acclaimed 2016 Pinot Cup for its stellar Pinot Noir).

Sebastopol is also where you come for inventive, handcrafted, and sustainable dining, like Ramen Gaijin and the French-meets-hyperlocal K&L Bistro, where most ingredients are from Sebastopol (on Sunday mornings, be sure to wander the downtown farmers’ market). Non-vegetarians, meanwhile, will love Zazu Kitchen + Farm from The Next Iron Chef contender Duskie Estes, who offers up bacon, bacon, and more bacon—all from her own sustainably raised pigs.

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Santa Rosa

Santa Rosa
Sonoma County’s biggest small city

Even though this is Sonoma County’s largest city (with 174,000 residents), Santa Rosa still feels pretty cozy. Certainly, you never forget you’re in wine country, with tasting rooms right in the heart of the city. One good place to start is Santa Rosa Vintners Square, a collection of wineries set in an industrial area on Cleveland Avenue next to U.S. Highway 101. It’s home to spots such as D’Argenzio Winery, Sheldon Wines, Krutz Family Cellars, and Fogbelt Brewing Company—all set around a lovely playground.

The SOFA arts district on South A Street is another off-the-radar gem, which has developed into a fashionable island for creative types like chef Liza Hinman and her Cal-Mediterranean Spinster Sisters restaurant (think ricotta-nettle gnocchi with hedgehog and black trumpet mushrooms, prosciutto, and green garlic). Stroll the historic neighborhoods around here too—like McDonald Avenue, where Alfred Hitchcock filmed Shadow of a Doubt in the summer of 1942.

Stroll historic neighborhoods like McDonald Avenue, where Alfred Hitchcock filmed Shadow of a Doubt in the summer of 1942. 

This is also where you’ll find some of Sonoma County’s best shopping. The Railroad Square Historic District sits on the west side of Highway 101, stretching from the Hyatt Vineyard Creek Hotel to the ranch supply shop West End Farmers Market, and all centered around the restored 1903 Northwestern Pacific Railroad train depot. Browse longtime favorites like Hot Couture, with its vintage ball gowns, or the delicate china teacups perfect for pinky-lifting at Whistlestop Antiques.

You’ll also notice several larger-than-life statues of Snoopy around town, as well as statues of Charlie Brown, Woodstock, and Lucy. That’s because Charles Schulz lived and worked in Santa Rosa from 1969 until his death in 2000, claiming Sonoma County as one inspiration for his iconic Peanuts comic strip.

Robert Fried/Alamy

Guerneville

Guerneville
This burgeoning destination still has a quirky heart

Back in in 2008, Guerneville was a sleepy Russian River hideaway best known for spectacular natural wonders like primeval redwood forests, year-round waterfalls, and the backcountry wilderness spanning the nearly 6,000-acre Austin Creek State Recreation Area. Today, the tiny town of less than 5,000 people is still a shining jewel of Sonoma’s County West Coast vibe, but it’s also become a hip dining destination and a burgeoning resort retreat.

Boon Hotel + Spa, for instance, is an intimate, eco-chic retreat on the edge of the 805-acre Armstrong Woods State Natural Reserve. Its sister restaurant Boon Eat + Drink sits a few blocks away on Main Street, near Big Bottom Market (best biscuits ever) and El Barrio bar, which brings tequila, mezcal, and bourbon to wine country. But don’t think fancy attitudes: The town’s heart is still an eclectic mix of dark but convivial bars, so-tacky-they’re-fun souvenir shops, quirky art galleries, and modern hippie types looking to escape big-city bother. There’s also plenty of flair from the drag queens and alt-lifestylers who’ve made Guerneville their home.

To see how down-to-earth culture translates into wine, taste the certified biodynamic wines from the mountainside Porter-Bass Winery, inhabited by winemaker and Earth child Luke Bass, his heritage chickens, tail-wagging coonhound, and saluki dogs. Before you leave town, kick back with the locals at Johnson's Beach, a slip of sand beckoning beneath Guerneville’s entryway bridge with rentable beach chairs, canoes, kayaks, and pedal boats. 

When morning fog rolls up the Russian River, it provides natural air conditioning that is a key factor in growing superb grapes.