Cloverdale

At Sonoma's northern edge, where 101 begins its climb toward Mendocino, Cloverdale is the threshold town: a restored 19th-century main street that once ran on railroads and citrus. Wine here lives on the boundary between two counties, a slower sensibility than the corridor to the south. Stay in an independent inn, taste across the upper Alexander Valley, and use the town as a launch point for everything further north. To explore the north, you start right here.