Upscale and chic without jumping to pretentious, visitors and locals alike head to Healdsburg when they want to dine in world-class restaurants, shop stylish boutiques, or sip wine while touring fashionable galleries. The action revolves around the historic Healdsburg Plaza, a one-square-block park in the heart of town with a pretty fountain, walkways for promenading and a gazebo bandstand that hosts frequent free concerts.
There’s always something happening on the Plaza or a short stroll away. The Second Saturday Artwalk links receptions at some 30 galleries, giving art aficionados an opportunity to meet featured artists. Cooking classes teach what to do with delectables from the Farmers Market, just a couple blocks west. Outdoor events like the biannual Healdsburg Antiques Fair attract enthusiastic collectors, and excellent live performances make the Raven Performing Arts Theater popular year-round. Because this is Wine Country, there’s no shortage of in-town tasting rooms. But Healdsburg is happily situated where three top appellations intersect -- Russian River Valley, Dry Creek Valley and Alexander Valley – and that means plenty of wineries are nearby.