Introduction

One of Northern California’s most picturesque small towns, Healdsburg is the epicenter of northern Sonoma wine country. Built around a leafy central square called the plaza, the town’s quiet side streets are lined with Victorians and white picket fences—like something out of a Norman Rockwell painting. When friends come to visit and want to see Wine Country, I take them to Healdsburg.

For years the biggest annual event was the Future Farmers Parade, with little children riding on flat-bed trucks, proudly holding up newborn lambs, and oddball farmers with muddy boots solemnly carrying the American flag. Times are changing. Some of Healdsburg’s beloved old weirdoes are being driven out as second- and third-home owners arrive in Range Rovers and Hawaiian shirts, come in search of the elusive ‘wine country lifestyle.’ Lately the town feels homogenous, gentrified by the parvenu.

But the news isn’t all bad. Healdsburg has emerged as Sonoma County’s gastronomic capital, with spectacular farmers markets, gourmet food stores, white-tablecloth restaurants, and dozens of top-flight wineries, making it the perfect place for an extended weekend of hedonism. If you’re an old-school boho, fear not: the Future Farmers Parade still happens every year, and there are weirdoes here and there, like at the annual Rock, Paper, Scissors tournament at Roshambo Winery. You just need to know where to look.

See & Do in Healdsburg

Window-shopping the plaza and wine-tasting are the primary activities, but there’s plenty to keep you busy once your teeth have turned purple and you’ve maxed out your credit cards.

Find a winery near Healdsburg to suit your personal taste.

On Tuesday afternoons in summer, the whole town heads to the plaza for the dynamic and wonderful Healdsburg Farmers Market, with food, crafts, and live music. Parking can be tricky, so arrive early. There’s another market on Saturday mornings at North and Vine Sts., but the big fun happens Tuesdays.

Grapes are Sonoma’s new cash crop, but there’s a rich, diverse agricultural tradition beyond winemaking. Pick up a copy of the Sonoma County Farm Trails Guide, which lists everything from u-pick-em organic fruit orchards and flower farms, to cheese makers and beekeepers, all open to the public. Do you love flowers, but suck at arranging them? Bone up on your bouquet-making skills at Dragonfly Farm, using posies grown right outside; the fields explode into color in May, but classes happen all year.

One of the best ways to tour northern Sonoma’s stunningly beautiful landscape is by bicycle or canoe. It’s easier than you may think to pedal between wineries or paddle down the Russian River. Contact Getaway Adventures for top-notch bike and paddle tours, led by savvy guides who love to have fun. If you prefer to go it alone, rent a canoe (or kayak) with River’s Edge Kayak & Canoe Trips and float downriver at your own pace.

If you’re into thrift shopping, you’ll flip out when you see the Healdsburg Salvation Army. Staffed by recovering alcoholics and frequented by an odd mix of hipsters and the down-trodden, the gigantic store stocks some real treasures — if you’re willing to sift. Take the Lytton Springs exit off of Hwy 101, north of town; the store is immediately west of the highway.

Plan the perfect picnic to take winery-hopping: find Healdsburg’s best specialty-food shops here.

Healdsburg Restaurants: The Scene

There’s no shortage of midrange and high-end options, but the local culinary landscape changes fast. Last year stunning Cyrus ($$$$) burst onto the scene and edged out Madrona Manor ($$$$) for top honors in Sonoma County; no word yet on how Madrona Manor is faring, but I’m planning to dine there this spring—will keep you posted.

Your Zagat guide doesn’t say so yet, but once-great Willi’s Seafood and Raw Bar ($$$–$$$$) has gone downhill, as has Manzanita ($$$). Take heart: Santi ($$–$$$$), that outpost of rustic Italian cooking in neighboring Geyserville, is going strong. Once I’ve had lunch on the patio this fall, I’ll give you the latest, but for now consider it a solid choice.

Two years ago Bovolo ($$) set up shop on the Plaza and instantly became one of my new favorites. The order-at-the-counter café imports the clean, bright flavors of rustic Italian cooking to Healdsburg. Also a new favorite, Ravenette Café ($$) serves up stellar Euro-Cal comfort foods, all sensibly priced. Zin ($$–$$$) is the spot for down-to-earth preparations of American-inspired classics—think pot roast, and pork chops with applesauce—all designed to pair well with the local wineries’ specialty: Zinfandel.

And then there’s Cyrus ($$$$), a high-wattage culinary experience on par with the world’s best. From the ballet-like service to the superb artistry on the plate, this is one meal you’ll remember for a long time.

Read full-length reviews of our current favorite Healdsburg restaurants.

Healdsburg Bars & Coffeehouses

By day, the in-the-know crowd heads directly for Flying Goat Coffee, one of Northern California’s premier coffee roasters. Subscribing to the ‘Third Wave of Coffee’ concept, Flying Goat’s organic fair-trade beans are roasted daily, every cup is ground to order, and all the pastries are made in-house. To get jacked on caffeine with local bon vivants, this is the spot.

When you’re dressed up for a night on the town, head to Cyrus for hand-muddled cocktails and bar food from the restaurant’s magnificent kitchen. If you’re not up for being surrounded by socialites in two-thousand-dollar outfits, head to the boho-fancy Barndiva, which mixes some damn good specialty drinks — but they cost twelve friggin’ dollars. (If you’re on a budget, stick to the $7 well drinks.) Barndiva is the only place in town safe for urbanites who want to get hammered and (loudly) feature their urbane wit.

Unlike at the local dive bars. Of Healdsburg’s two slummin’ joints, pick the B&B Lounge. Everyone will stare when you walk in, but the crowd is ultimately friendly—mostly waiters playing pool after their shifts have ended. Skip the bar that fronts directly on the plaza; locals tell me that bartenders don’t break up fights, even when they’re entirely unfair and unjustified – bad news for a cashmere-clad city slicker.

Read full-length reviews of my current favorite Healdsburg hotels and inns.

Healdsburg Hotels and Inns

I’ve seen nearly every place in town, but have only listed those I like best. Read the complete reviews.

The first-choice Hotel Healdsburg & Spa ($$$$) has a decidedly minimalist, fashion-forward decor that blends soft earth tones with hard-edged industrial materials like poured concrete, wood, and tile. Belle de Jour Inn ($$$$) is one of Healdsburg’s original bed-and-breakfast inns, with six acres of lovely hilltop gardens and hideaway cottages perfect for a lovers’ tryst.

Healdsburg Inn on the Plaza ($$$$) got a complete renovation in 2005: everything looks crisp and fresh, with a soothing khaki color scheme—and it’s right on the plaza. The Honor Mansion ($$$$) dates to 1883 and exudes stately charm. Rooms are individually styled with an eclectic mix of European antiques; outside there’s a fabulous pool and vast croquet lawn.

The crown jewel of Healdsburg inns, Madrona Manor ($$$$) sits atop a high hill – a stunning 1881 Victorian mansion, dripping with gingerbread trim and surrounded by eight acres of jaw-droppingly beautiful gardens. You know you’re somewhere special the moment you drive through the gate and up the winding driveway beneath gracefully arcing, century-old trees.

There’s not much budget lodging in Healdsburg; the Best Western Dry Creek Inn ($$) is the best of town’s four motels. Rooms are standard-issue and style-free, but they’re spacious and clean. All were redecorated this past spring.

Vacation Rentals

Whether you’re a budget traveler who can’t afford the double-whammy cost of hotels and restaurants, or a luxury traveler who wants seclusion and over-the-top grandeur, you’ll get more space and privacy for your money by booking a rental property. And you’ll have a kitchen too. Healdsburg vacation rentals.