The menu at Chalkboard, in a building just off of Healdsburg’s main square, features exactly what guests in wine country are hankering for: small plates to accompany their sips of wine. Features of the menu include maple-glazed pork belly biscuits with pickled onions and chipotle mayo and housemade pasta like porcini mac & cheese made with smoked white cheddar, toasted garlic and Calabrian chili. Most dishes include at least one fresh ingredient grown in the nearby Chalk Hill Gardens.

Many claim that this local favorite eatery serves the best pizza in the county. Geyserville is another eight miles north of Healdsburg, but Diavola’s thin-crust pizzas alone are worth the journey to the adorable town. The Sonja pie, with mascarpone, prosciutto and arugula, is a particular favorite.

This retro-chic spot in the center of Healdsburg has two specialties: pie and ice cream. All versions of both treats are homemade in house and range from traditional (summer berry pie) to more funky (jasmine ice cream). The offerings change with the seasons and what’s available, so each visit throughout the year will yield new findings.

For a special night out in Healdsburg, in-the-know visitors and locals head to Valette, a Sonoma restaurant that skews towards the formal with its cuisine and atmosphere. The eatery is family-owned, which adds a personal touch to the place, which can feel a bit overly refined. Exemplary dishes, like the scallops en croute and cacao-nib crusted duck breast, are crowd favorites and pair beautifully with certain local wines.

Though it’s located well off the beaten path, this bakery’s homemade treats are worth the journey. Particular favorites include the sticky buns and scones, which are on offer to eat in or take out along with good quality coffee.