Explore all of the amazing wineries in Dry Creek Valley along Dry Creek Valley Road right outside of the Healdsburg Square. Some of our favorites are Dry Creek Vineyard, Lambert Bridge, Truett Hurst and Unti. Don't forget to stop into the Dry Creek General Store (on Dry Creek Road) to pick up some sandwiches - Josh's favorite is the Bark Shark. You can eat at the General Store or pack a picnic and take it to one of the vineyards (most allow picnics!).
Only 30 mins south of Healdsburg is Lagunitas Brewing Company. It is also right on the way to Healdsburg when you are driving up from SF. There is a awesome outdoor area where you can enjoy good beer and food and often times live music.
If you are looking to do something active in between drinking wine, take a drive to Lake Sonoma (only 20 mins from Healdsburg) and explore some of the beautiful trails.
Healdsburg Square is filled with countless shops, restaurants and wine bars. We are big fans of Willie's Seafood and Raw Bar, The Shed, Duke's Common and Bravas de Tapas.