in Healdsburg Scopa is right on the plaza and shouldn't be missed. (owned by the same people as Campo Fina)
Bergamot Alley for wine (nothing from the new world though) you can also bring food from campo fino into bergamot.
other places i can recommend are Barn Diva, Chalkboard, Parish (for Po' boys or gumbo), Bravas ) for tapas, The shed for sandwiches or coffee, the french bakery (can't remember the name) right on healdsburg ave is great for lunch, flying goat for coffee.
Bistro Ralph's on the plaza attracts a lot of locals and is kind of an institution in healdsburg. the vibe is fun but th food is pretty average. oddly enough, the wine list is pretty boring.
that should get you started.