Healdsburg Plaza

Healdsburg is the small town that wine lovers fall for, and its plaza is the reason. About ninety minutes north of the Golden Gate Bridge, this town of around eleven thousand people is built around a Spanish-style square of lawns, redwoods and palms with an outdoor bandstand, a plaza that Travel and Leisure once named among America's most beautiful town squares. On the streets around it you will find more than two dozen winery tasting rooms within walking distance, alongside some of the best restaurants, bakeries and bars in Sonoma County, and a stylish run of galleries, antique shops, clothing boutiques and bookstores. Beyond town, more than a hundred wineries and tasting rooms are a short drive away in three very different valleys: Dry Creek Valley, famous for Zinfandel and Sauvignon Blanc; the cool Russian River Valley, home of Pinot Noir and Chardonnay; and Alexander Valley, known for rich Cabernet Sauvignon. That combination makes Healdsburg the most rewarding base in Sonoma County if you want to walk to dinner and still reach serious wineries in ten minutes. Breakfast at Costeaux French Bakery, in business since 1923, is a local ritual; Barndiva is known for farm-sourced cooking; Willi's Seafood and Raw Bar and Bravas Bar de Tapas are favorites for small plates; and Spicy Vines pairs tastings with small bites and live music on many Saturday nights. Free concerts and antique fairs fill the bandstand in summer. The catch is price: Healdsburg has gone upscale, and hotels, restaurants and tasting fees reflect it. But for a walkable, food-focused wine weekend, it is the best small town in California.

How Healdsburg grew. The town was laid out in the 1850s by Harmon Heald, an Ohio-born settler who opened a store on the road north, and for a century it was a farm town of prunes, hops and grapes. The modern boom came as the surrounding valleys earned international reputations for wine, and the plaza, once a quiet country square, became the region's social center. Today it mixes old-timers and weekenders, farm trucks and design hotels, and the scale is still small enough to walk everything in an afternoon.

Tasting on and off the plaza. If you are staying in town, the plaza tasting rooms let you sample wines from many of the surrounding valleys without driving. Some stay open later in the evening, which is rare in wine country. For a deeper day, hire a guide or join a bike tour: local outfitters run cycling trips into Dry Creek Valley, where quiet roads link family wineries, and a ten-person party bike is a lively option for groups. Reservations are recommended at most wineries, especially on weekends and in harvest season.

Making a day of it. Start with pastries and coffee on the plaza, taste through the morning, and eat a long lunch before heading out to one or two valley wineries in the afternoon. In warm weather, the Russian River is close for a paddle or a swim, and Armstrong Redwoods near Guerneville is about thirty minutes southwest. Evenings are for dinner on the square and a nightcap at one of the cocktail bars nearby. If you are driving between wineries, pick a designated driver or book a car service; country roads and tasting pours do not mix.