Healdsburg, CA

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, 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 as second- and third-home owners arrive in Range Rovers and Hawaiian shirts, come in search of the elusive ‘wine country lifestyle.’ 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.