Wine & Food Affair

Every early November, as the last grapes come off the vine and the vineyards turn gold and russet, Wine Road throws open the doors of dozens of wineries across the Alexander, Dry Creek, and Russian River valleys for its Wine & Food Affair. The premise is simple and irresistible: at each stop, a winery pairs a favorite wine with a favorite recipe, from hearty chilis and sliders to cheesecakes. It's been a north-county ritual since the late 1990s, and its signature flourish is the cookbook — the dishes are collected so you can carry the weekend home. Guests roam at their own pace, glass in hand, letting the countryside set the tempo.

Go for the pairings, but stay for the sense of place. Spread across three of Sonoma's great appellations with no single venue, the Affair turns a fall weekend into a self-guided loop through Healdsburg and the valleys around it — arguably the prettiest time of year to drive them. A single wristband and keepsake glass carry you from winery to winery, where the pours come with genuine cooking rather than crackers, and every recipe lands in Wine Road's online cookbook for later. Buy the designated-driver ticket for a non-drinking companion, come hungry, and pace yourself; the event routinely sells out, so tickets are worth securing in advance.