Planning a trip to Healdsburg this summer? Or maybe you're a local looking for something new to love? Whether you’re into food, wine, art, or just soaking up small-town charm, Healdsburg delivers. Here’s your definitive summer guide—filled with locally loved experiences that showcase why this Northern California gem is one of Wine Country’s most sought-after destinations.
1. Relax at Healdsburg Plaza: The Heart of Downtown
The Healdsburg Plaza is more than a town square—it’s the social living room of the community. Surrounded by tasting rooms, galleries, shops, and restaurants, it’s the perfect place to start your day or wind it down. Pro tip: Grab a cone from Noble Folk or a coffee from Black Oak and claim a bench under the old oaks.
2. Enjoy a Sunset Wine Tasting at Reeve Wines
One of the best wine tasting experiences in Healdsburg, Reeve Wines offers small-lot pours in a dreamy hillside setting. Think outdoor lounges, vineyard views, and a distinctly relaxed, elevated vibe.
3. Float the Russian River
The River's Edge kayaking and canoeing is a Healdsburg summer rite of passage. Launch from Veterans Memorial Beach for an easy, scenic float. You’ll see egrets, turtles, and if you’re lucky, zero emails.
4. Dine at Valette: A Healdsburg Culinary Favorite
When people Google “best restaurants in Healdsburg,” Valette comes up for a reason. Seasonal, local, and run by a pair of brothers who grew up here, it’s a top-tier dining experience without any pretense.
5. Catch Live Music at Healdsburg Plaza
The town’s free summer concert series turns the Plaza into a nightly gathering spot. Bring a blanket, a bite from Oakville Grocery or Bravas, and enjoy live music under the stars.
6. Brunch and Browse at Little Saint
This multi-use space is redefining farm-to-table dining in Healdsburg. Come for the plant-based brunch, stay for the curated shop, rooftop, and art events. A stylish must.
7. Explore Healdsburg’s Art Galleries
Discover why Healdsburg is a rising art destination. Start with the Paul Mahder Gallery and work your way through Erickson Fine Art and upstairs spaces like Stafford Gallery.
8. Sip Margaritas and Savor Tacos at El Farolito
If you’re looking for authentic Mexican food in Healdsburg, El Farolito delivers. Classic tacos, zesty margaritas, and zero frills—just bold flavors and local love. Perfect for an easy evening.
9. Book a Picnic at Jordan Winery
Experience one of the best wine and food pairings in Healdsburg with a picnic at Jordan Estate. It's elegance without stuffiness, surrounded by views that rival Napa.
10. Visit the Healdsburg Farmers’ Market
Held on Tuesdays and Saturdays, the Healdsburg Farmers' Market is a celebration of Sonoma County’s agricultural richness. Pick up produce, pastries, flowers, and more—all grown or made nearby.
Discover Healdsburg Like a Local
Healdsburg is more than just a pretty Wine Country town—it’s a place of layered charm, deep flavor, and relaxed sophistication. At Live Wine Country, we bring you the insider’s guide to everything that makes this place shine. Whether you're booking a stay, buying a home, or just planning the perfect weekend, start here.
