Chalk Hill Estate is a sprawling 1,477-acre property in Healdsburg where you can bring your dog along while tasting wine among oak woodlands and natural streams. The estate has 350 vineyard acres divided into 60 different small vineyards, each producing distinct wines. It’s the kind of place where you can actually walk around and see the landscape rather than just sitting in a tasting room.

The setting itself is what makes a visit here different from many other Sonoma County wineries. You’re surrounded by heritage oak trees and riparian streams, so there’s real terrain to explore. Your dog will appreciate the space to move around, and honestly, so will you after being in the car. The vineyard layout means the wines reflect different aspects of the property’s terroir — elevation changes, soil variations, exposure — so there’s something genuinely interesting to understand about what you’re tasting.

Dogs are welcome throughout the estate, which means you’re not confined to a single tasting area. You can move through the property with your dog at a pace that works for you both. This matters more than it sounds — some wineries feel cramped or stuffy, but Chalk Hill’s scale and open layout give you room to breathe and let your dog move naturally without feeling like you’re disrupting other guests.

The wines themselves have a reputation for being well-made and substantial rather than trendy. They focus on Chardonnay, Pinot Noir, and Cabernet Sauvignon, among others, so you know what to expect quality-wise. A visit here works well if you want to combine some serious wine tasting with actual time outdoors. Plan to spend a few hours rather than rushing through — you’ll get more out of the experience and your dog will be noticeably more content than if you’d left them at the hotel. Head to their website to check current tasting reservations before you go.