Big, bold Sonoma reds since 1984, still family-run with a take-nothing-seriously-but-the-wine spirit. The Healdsburg room hides behind a gate beside Longboard Vineyards, a few blocks off the Square — pours in a working cellar, a tucked-away patio, and that hand-painted Handprint Merlot. Walk-ins welcome.

One of the West Sonoma Coast's most revered estates, planted on a remote ridge above the Pacific and farmed biodynamically. The estate is closed to the public, so this appointment-only room at Old Roma Station is where you taste its acclaimed Pinot Noir and Chardonnay. Book ahead; seats are few.

Truett Hurst's Tasting Barn fills the 1903 French-American cellar at Old Roma Station, opened in late 2024 under founder Phil Hurst and vintner Ken Wilson. The flight runs Dry Creek and Russian River wines — a Zinfandel-rooted range — in a vintage-modern room steps from the river. Closed Tue–Wed.

A cooperative tasting room "where the river meets the tracks," in the 1890 cellar of one of Healdsburg's first wineries. Since 2006 it has gathered a handful of small family producers under one roof, pouring limited-production reds, whites, and rosés side by side. Walk-ins welcome; picnic area out back.

A historic cluster of 1870s–90s brick winery buildings on Hudson Street, "where the river meets the tracks," a short walk from the Healdsburg Plaza. Today it's a one-stop tasting hub — Holdredge, Sapphire Hill, Pezzi King, the Hudson Street co-op, and more — with bikes, shops, and easy parking.

Healdsburg's standard-bearer for Zinfandel, planted by Edoardo Seghesio in 1895 and farmed by five generations since. A few blocks northeast of the Plaza, the room opens onto The Grove — a shaded lawn with bocce courts made for a glass. Worth the short walk for the Zin.

A New California Wine pioneer dreamed up behind Spago Beverly Hills — restrained, oak-free Chardonnay plus Pinot, old-vine Carignan, and Valdiguie, all from organic, dry-farmed ranches. The Lickliders' sleek, retro-cozy room just off the Healdsburg Plaza pours flights and small plates, with live music and industry nights.

Chemist-turned-vintner Bob Mueller founded his label in Healdsburg in 1991, chasing small-lot Russian River Pinot Noir and Chardonnay. His acclaimed "Emily's Cuvée" Pinot leads a lineup that includes old-vine Zin and Syrah. The intimate room — Bob often pouring — is open weekends or by appointment.

A sprawling, light-filled hub a block off the Healdsburg Plaza — wine lounge, bottle shop, 100% plant-based restaurant, and live-music venue in the former SHED. Owners Laurie and Jeff Ubben pair farm-driven bites with thoughtful pours, plus free Thursday-night music upstairs at The Second Story.

The "Cal-Ital" winery of married founders Jane Portalupi and Tim Borges, on the Healdsburg Square since 2011. Don't miss Vaso di Marina — wine in a milk jug, honoring Jane's Piemontese grandmother — alongside Zinfandel, Barbera, and Charbono in a sleek, warehouse-chic room. Open daily.

Hartford's downtown salon is the in-town counterpart to its secluded Green Valley estate near Forestville, pouring the same expressive, single-vineyard wines off the square. The focus is Russian River Pinot Noir and Chardonnay plus old-vine Zinfandel — 'high personality' wines, as the family puts it. Dogs welcome on the patio.

Named for the Babylonian goddess of wine, Siduri is built on one obsession: cool-climate, single-vineyard Pinot Noir. The relaxed Healdsburg lounge is its home — cozy seating, a vinyl collection, and a signature flight that travels a thousand miles of coastline in a single sitting.

David Ramey is one of California's most respected winemakers, and the family's urban winery near Memorial Bridge is where you taste why — elegant, balanced wines built to age. Tastings are seated and by appointment in an upstairs parlor over the cellar, six wines across about ninety minutes.

Marine Layer is named for the fog that makes its wines possible — authentic, cool-climate Chardonnay and Pinot Noir drawn from windswept coastal vineyards. The light-filled room on Center Street pours flights by day and shifts to wines by the glass after 5pm. Reservations recommended; walk-ins welcome when there's room.

Founded in 2012 by Texas-raised Erin Brooks, Ernest makes cool-climate, single-vineyard Chardonnay and Pinot Noir from the far West Sonoma Coast, low-intervention and bright. Its chic Healdsburg lounge, steps from the Plaza, pours current and library flights, plus the exploratory Edaphos label.

Selby is the oldest tasting room downtown, owned and run start-to-finish by Susie Selby a half-block off the square. The wines are well-made and unpretentious — and have been poured in the White House since 1995, across four administrations. A quiet, friendly stop with a small patio.

Celebrated natural winemaker Martha Stoumen — a Sebastopol native farming for healthy soils and minimal intervention — opened her first tasting room steps from the Healdsburg Plaza in late 2025. The copper-toned, open-late room pours six-taste flights of southern-Italian varietals and her playful Post Flirtation blends.