Nestled 90 minutes north of San Francisco lies the idyllic town of Healdsburg, the heart of California Wine Country. With its charming plaza boasting around 40 tasting rooms, and many more throughout the three surrounding wine regions, Healdsburg beckons visitors to unwind and savor the region’s finest varietals. A relaxed atmosphere envelops you as you wander through the picturesque town of Healdsburg, flanked by acclaimed restaurants, world-class wineries, and eco-conscious hotels.
Healdsburg’s unique blend of urban energy and small-town charm sets the scene for an unforgettable happy hour experience.
Must-Try Happy Hour Sports in Healdsburg
Arandas
The newest restaurant in Healdsburg offers a great Happy Hour menu all week long! From classic chips and guac and $5 margaritas to unique finds like their Mexi-Mule, Arandas brings the soul of Mexican cuisine to downtown Healdsburg (and at a great price during Happy Hour!).
Happy Hour: 2 PM – 6 PM Wednesday – Sunday
Goodnight’s Prime Steak + Spirits Local’s Hour
Happy Hour: 4 PM to 5:30 PM, Tuesday – Saturday
The Rooftop at Harmon Guest House
Soak in the breathtaking views of Healdsburg from the Rooftop at Harmon Guest House. Their happy hour features enticing drink specials and small plates, perfect for an elevated after-work experience.
Insider Tip: Visit on a Monday for $1 oysters! Pairs beautifully with their The Rooftop namesake cocktail.
Spirit Bar at Dry Creek Kitchen
Nestled inside the luxurious Hotel Healdsburg, Spirit Bar offers a relaxed and cozy atmosphere. Unwind after a day of wine tasting with creative cocktails and inventive bar bites from their Happy Hour menu.
Insider Tip: Be sure to check out their website for their live jazz nights by the fireplace!
Happy Hour: 5 PM to 7 PM, Sunday – Thursday
Pizzando
Nestled in the heart of Healdsburg, Pizzando offers a lively happy hour experience with a focus on wood-fired pizzas and craft cocktails. Gather with friends and savor the flavors of their signature pies, like the Margherita with fresh basil and creamy mozzarella, or the Salsiccia with spicy Italian sausage and roasted peppers. Pair your pizza with a selection from their extensive wine list or a refreshing cocktail made with locally sourced ingredients.
Insider Tip: Don’t miss their Aperol Spritz, a perfect balance of bittersweet Aperol and sparkling wine.
Happy Hour: 3 PM – 5 PM, Monday through Friday
Little Saint
For a lively and social atmosphere, head to Little Saint’s happy hour. This local favorite offers handcrafted cocktails alongside delicious light bites, perfect for sharing with friends. Their plant-based menu with fresh ingredients from the Little Saint Farm will leave your plates and cocktails looking like works of art. Pair your drinks with savory snacks like our trio of dips: smoked carrot, cultured cashew, and artichoke hummus. Reservations available to lock in your spot and skip the wait. Little Saint offers $8 Classic cocktails or Wine (including NA options) and $7.50 Cold Draft Beer.
Insider Tip: Check out their free concerts upstairs every Thursday!
Happy Hour: 3 PM to 6 PM, Thursday through Monday
The Matheson
Enjoy the bar and Wine Wall at the Matheson everyday during their Happy Hour. From small bites like Furikake Popcorn and Duck Confit Empanadas, to their iconic Broccolini Pizza, this is the spot to be from 4 – 6 pm.
Insider Tip: Stop by for their Winemaker Wednesdays where a different winery is featured every week with complimentary tastings and a live recording of Sonoma County Vintners’ Vine + Wine + Dine radio show.
Happy Hour: 4 PM to 6 PM, Everyday
Costeaux French Bakery – NEW!
Join Costeaux French Bakery for a curated happy hour experience, featuring a range of culinary delights. Indulge in savory selections such as tangerine marinated olives, delicate pâte à choux bites, petite tartines, flavorful beef sliders, crispy pomme frites, grilled Parisian sandwiches, and classic deviled eggs. Finish your culinary journey with petite rum crème éclairs. Enjoy local beer and wine by the glass or bottle.
Happy Hour: 3 PM to 6 PM, Wednesday through Friday
BONUS: Reverse Happy Hour at Roof 106
Wind down (or turn up!) with our Reverse Happy Hour, offered daily at Roof 106. Enjoy after-hours specials on cocktails, wine, pizza frittas, smash burgers, and more—ideal for a late-night bite or casual nightcap. Available Monday through Sunday. Parooze the menu HERE.
