Making wine from ground to glass, by hand and heart in Rancho Santa Ynez for three generations, Carhartt is a family-owned winery where you’ll actually meet the people doing the work. The tasting room sits just one block north of the Flagpole in downtown Los Olivos, which means it’s walkable from the other shops and galleries that line the main drag. Don’t expect a sprawling facility—this is literally called the “World’s Smallest Tasting Room,” and that’s part of its charm. It’s an intimate space where you can taste their full range of current wines and chat directly with Brooke, Mike, and Chase about what they’re making.

Dogs are completely welcome here, which makes sense in a town where you’ll see them wandering in and out of other businesses. The casual, no-reservations first-come, first-served setup means you can drop by whenever you’re exploring Los Olivos, though you’ll want to check their website for current hours since they’re not open every single day. There’s something refreshing about a winery that doesn’t require advance planning or feel overly formal—you just show up, and if they’re open, you’re in.

If you fall in love with something while you’re there, you can also order through their website store. But honestly, the point of visiting is to taste with the people who actually made the wine and get their take on what’s in your glass. Los Olivos itself is dog-friendly enough that you could easily spend an afternoon wandering around, hitting a few tasting rooms or picking up lunch, and your dog will fit right in. The town has that relaxed, walkable vibe where dogs are just part of the scene.