Cruise the plaza for shopping and wine tasting
A great spot in the square for oysters, seafood and small share plates.
If you’re up for rooftop vibes and killer cocktails, Roof 106 at The Matheson is a must. You’ll find a glowing copper bar, fire pits, plenty of greenery, and a menu of wood-fired small plates and seasonal pizzas.
If you’re in the mood to taste your way through Sonoma in small sips, check out The Matheson’s Wine Wall — it offers 88 wines on tap, so you can explore flights, half-glasses, or full pours without the commitment.
Where I met Jordan! Located in the Healdsburg Plaza, Bravas Bar de Tapas is a celebrated spot serving Spanish small plates and sangria in a modern space.
Folia is the new restaurant at the Appellation Hotel by chef Charlie Palmer—fresh, seasonal, and beautifully done. It’s an upscale farm-to-table spot with a relaxed wine country feel, perfect for gathering over great food and good wine.
If you’re feeling a little swanky and want to kick off Friday night with something special, we recommend heading up to Andy’s Beeline Rooftop Bar at the new Appellation Hotel by Charlie Palmer. With sweeping views over Healdsburg’s hills and vineyards, it’s the perfect spot for cocktails, wine, and soaking in that golden-hour wine country magic.
Quail & Condor is an absolute must—everything they make is incredible. It’s a grab-and-go bakery, and while the line can get a little long, it’s totally worth the wait. Recently named one of the Top 20 Bakeries in America by The New York Times, it’s a perfect stop for your morning coffee and pastries.
Home of the best morning buns around. Worth the early stop.
If you’re craving a laid-back morning spot, Acorn Cafe in downtown Healdsburg is a go-to. With creative brunch fare (hello tiramisu French toast and shakshuka), and patio seating, it’s perfect for fueling up before the wedding afternoon!
If you’re looking for something relaxed and delicious, Troubadour Bread & Bistro is a top pick. They bake fresh sourdough daily and make big, seasonal sandwiches (great either to grab and go or eat outside).
If you’re in the mood for a peaceful wine tasting with stunning views, we recommend visiting MacRostie Estate House (4605 Westside Road). Their guided tastings spotlight Chardonnay and Pinot Noir set against sweeping panoramas of the Russian River Valley—relaxing, immersive, and completely worth it. Be sure to make a reservation ahead of time <3