Downtown Healdsburg is entirely walkable. The central plaza, tasting rooms, restaurants, and most of the shops occupy a compact grid that takes about ten minutes to cross on foot. Nearly everything worth doing in town is within a five-minute walk of the plaza.
Beyond downtown, a car is essential. The wineries of Dry Creek Valley, Alexander Valley, and Russian River Valley are spread across 20 to 40 km of back roads, and the distances between them make walking or transit impractical. Most visitors rely on their own car or hire a driver for the day if they plan on tasting seriously.
Cycling is viable in parts of Dry Creek Valley, where the valley floor is relatively flat and the traffic light. Bike rentals are available from several shops in town. Westside Road along the Russian River is scenic but narrow and can feel uncomfortable on summer weekends when traffic picks up.
Rideshare services (Uber, Lyft) operate in the area but coverage is thinner than in a city — during peak times and late evenings, waits can be long. Several wine country shuttle and taxi services operate out of Healdsburg for groups who prefer not to drive.