Unlike Healdsburg, Sebastapol is still the authentic, laid back Sonoma outpost it was a generation ago. Dive right in beginning at Aubergine Vintage Emporium, a hangar-like space where you might pick up anything from a broken-in aviator jacket to a Soviet Army-issued canvas belt. Hidden behind the clothing racks are a cavernous live music venue and a bar with an open patio. If you’re of a spiritual rather than spirits bent, wander up to Many Rivers Books & Tea, a cozy bookshop stacked high with New Age and philosophical tomes and figurines. In the tea shop at the back, pick up a bag of Monk’s Blend, a smooth malty mix of assam, darjeeling, keemun and nilgiri. For a light lunch, head to The Barlow, a cluster of restored warehouses once home to an apple processing plant. Sit out on the patio at Woodfour Brewing Company and try one of their Belgian farmhouse-style sours, mashed and boiled in the copper-plated tanks right behind the bar. Snack on cheeses from Petaluma, bratwurst, or Miyagi oysters.
Across the street, browse Scandinavian-inspired ceramics at the Passdoor. A small detour to nearby Guerneville would be worth your while, if only to check out Guerneville Bank Club, a historic bank building now housing the INIZI wine tasting room, a corner store specializing in handmade crafts, and the Nimble & Finn's ice cream parlor. Grab a cone of Bulleit Bourbon with chocolate-covered pretzels if it’s available. Take in the Russian River Historical Society’s exhibit at the back of the building, cataloguing Guerneville’s early days as a logging town. For dinner, make your way back to Sebastopol and to Peter Lowell’s for a farm-to-table menu of seasonal, rustic Italian fare. Wrap up your evening with a digestif at the Hopmonk Tavern, a vast space with a red banquette bar, concert venue and a Tuscan-inspired garden strung with lights.
Distance from SF: 1 hour 15 mins