The gastronomic capital of Sonoma County, Healdsburg is where artisinal bakers, cheese-makers, farmers, and winemakers showcase the best in seasonal-regional Northern California products. Cafés and specialty-food stores line the plaza, making it a snap to pack a picnic—and you can walk from shop to shop. Unlike in Napa, nearly every winery in Sonoma County allows on-site picnicking, so if you’re planning to winery-hop in Healdsburg, bring a goodie basket. And buy a bottle of your host’s wine—it’s only polite.
Everyone rushes to the Oakville Grocery, and with good reason: their selection of crispy-crust, pizza-like flatbreads, fat sandwiches, and fancy cheeses is spectacular, and it’s fun to sit on the giant outdoor patio and watch the world go by as you sip a glass of local zin. But Oakville is wickedly expensive and everybody goes here—if you’re feeling lazy and rich, this is the spot, but for my money, it’s more fun to make an adventure of assembling a picnic basket by visiting other shops around the plaza instead of the obvious one.
For some of the best artisinal salumi in Wine Country, head to Bovolo, a stellar Italian trattoria that will pack a picnic-ready rustic charcuterie plate to take away—they composed the plate in the above photograph. Before you leave, sample the housemade, fruit-dense gelato, worthy of a return trip at the end of the day.
Around the corner, pick up crusty loaves of bread and perfect pastries at the old-fashioned Downtown Bakery & Creamery. Town’s top bakery, it uses only locally sourced organic ingredients, from berries to butter. The counter staff could benefit from finishing school, but with so many wonderful creations to distract you, you’ll hardly notice the lackadaisical service. Be sure to pick up some of the stellar mint-chocolate cookies, and if you’re here in the morning, try the gooey-delicious sticky buns.
One of the best places to buy cheese in northern Sonoma County is the Cheese Shop, just north of the plaza in a strip mall. Service is perfunctory, downright terse even, but keep your eye on the prize: the best of the best European and domestic cheeses, including a great local selection by Bay Area producers.
If you’re heading toward the Alexander Valley, plan a stopover at the Jimtown Store, an old-fashioned country store that makes sandwiches using house-made condiments like fig-and-olive spread. Save room for chocolate pudding—if it’s not already sold out—and be sure to see the fabulously quirky antique shop in back, where you can pick up Mexican oilcloth, little wooden toys, and one-of-a-kind gifts to bring back home and remind yourself that yes, you actually do get out of town once in a while.