We highly recommend walking around Healdsburg Plaza. There are many cute shops, restaurants, etc. Most Healdsburg recs below are in and around the Plaza.
Troubador Bread & Bistro (sandwiches)
Bravas (Spanish-style tapas)
Guiso Latin Fusion
Little Saint (vegan)
Quail & Condor (baked goods)
LIOCO
Marine Layer Wines
Williamson Wines
*These are not on the square and a bit of a drive*
Ridge Vineyards
Iron Horse (sparkling)
Ryme
Russian River Brewing Company