Easily Sonoma County's ritziest town and the star of many a magazine spread or online feature, Healdsburg is located at the intersection of the Dry Creek Valley, Russian River Valley, and Alexander Valley AVAs. Several dozen wineries bear a Healdsburg address, and around downtown's plaza you'll find fashionable boutiques, spas, hip tasting rooms, and art galleries, and some of the Wine Country's best restaurants. Star chef Kyle Connaughton, who opened SingleThread Farms Restaurant in late 2016 to much fanfare, has motivated his counterparts all over town to up their game. The celebrity buzz could shift to the art scene if new owners, among them Annie Leibovitz, are able to rehabilitate a former machine shop at 444 Healdsburg Avenue and convert it into a gallery.
Especially on weekends, you'll have plenty of company as you tour the downtown area. You could spend a day just exploring the tasting rooms and shops surrounding Healdsburg Plaza, but be sure to allow time to venture into the surrounding countryside. With orderly rows of vines alternating with beautifully overgrown hills, this is the setting you dream about when planning a Wine Country vacation. Many wineries here are barely visible, often tucked behind groves of eucalyptus or hidden high on fog-shrouded hills. Country stores and roadside farm stands alongside relatively untrafficked roads sell just-plucked fruits and vine-ripened tomatoes.