California's first premium winery, founded in 1857 a mile northeast of the Plaza — the grand destination at the end of the walk. The historic grounds hold the 1862 Press House, hand-dug caves, a wine-tool museum, and a sparkling-focused Bubble Lounge, an easy half-day in themselves.

A wine bar and wine club a few blocks east of the Plaza, built around sommelier Todd Jolly's list of world-renowned wines and top spirits under a full liquor license. A marketplace and deli round out the space, and four cottages offer an overnight retreat. Easy and community-minded.

Winery Sixteen 600 is the family label of Phil Coturri, the viticulturist behind much of Sonoma Valley's organic farming, working from a 120-year-old farmhouse a block off the Plaza. Tastings are seated and comparative — certified-organic Grenache, Zinfandel, and Cabernet poured from antique theater seats while records play. By appointment.

WALT, the Hall family's Pinot label, works a room off the northwest corner of the Plaza, pouring Pinot Noir and Chardonnay from across the Pacific Coast — Sonoma Coast to Anderson Valley to Oregon. The signature flight runs a thousand miles of Pinot, with caviar and charcuterie alongside.

A literal red barn tucked off the Sonoma Plaza, pouring the down-to-earth Highway 12 and Highwayman labels — Sonoma red blends, Zinfandel, Trailblazer — from longtime friends Paul Giusto and Michael Sebastiani. Roadhouse-casual and dog-friendly, with $20 flights, chill tunes, and tented patio seating.

The shared tasting bar of partners Adam Webb and Mike Kuenz, whose 2004 winemaking odyssey yields small-lot Rhône and Iberian varietals — Syrah, Pinot Gris, rosé — raised in French Hogshead barrels. Just off the Plaza, it pours flights with cheese, charcuterie, and espresso on a covered patio.

Winemaker David Rossi's Pinot-centric label, built by cold-calling California's finest growers — small-lot, vineyard-designated bottlings from grand cru sites like Gap's Crown and Walala. The casual-elegant room sits just off the Sonoma Plaza; $35 buys five wines, and Rossi himself is often pouring.

Sosie — French for 'look-alike' — makes California wine in the image of the Rhône, the Loire, and Burgundy: Grenache Blanc and Marsanne whites, Pinot Noir, Syrah, picked early for acidity and restraint. The tasting room sits on Vine Alley, off the square. Built for the table.

An offshoot of the family's Della Santina's Trattoria, opened just off the Plaza in 2007 and built around a 250-bottle "wine wall" of hard-to-find local and international labels. Some thirty pour by the glass alongside the full trattoria menu — Old World, unhurried, and the town's living room.

Sojourn Cellars works from a quiet salon just off the square, pouring single-vineyard Pinot Noir, Cabernet, and Chardonnay side by side so the vineyards can be read against one another. Founded in 2001 by Craig Haserot and winemaker Erich Bradley. Friendly dogs welcome.

Kamen Estate is the downtown bar for Robert Kamen's Moon Mountain vineyard — the screenwriter planted it with the proceeds of his first script and farms it organically with Phil Coturri. The wines are mountain-grown Cabernet and Syrah, dark and structured. A block off the Plaza.

Pangloss Cellars fills a restored 1902 storefront on East Napa Street, named for the optimist of Voltaire's Candide. Winemaker Erich Bradley's Pinot, Chardonnay, and Grenache share the list with the Repris and Texture labels, poured in seated 90-minute flights with small-plate pairings.

SIGH is Sonoma's champagne bar, opened in 2012 by Sonoma native Jayme Powers after years with a California sparkling house. The list runs from grower Champagne to California sparkling and rosé, poured by the glass, the flight, or the occasional frozen slush. Walk in.

A glass-walled corner on the Sonoma Plaza where founder Lloyd Davis leads a seated, food-paired tour through seven Sonoma AVAs — each limited-production pour matched to a bite and explained. Twice named the best tasting room in the U.S. by USA Today readers, and proudly unintimidating.

Anchoring the north side of the Plaza since 1931, the Sonoma Cheese Factory carries one of the Square's largest selections of cheese and charcuterie. Wine flights pair with that charcuterie or house-smoked brisket off the patio smoker, alongside gelato from Italy and, come summer, frosé blended from sparkling rosé.

Three Sticks pours its estate Chardonnay and Pinot Noir inside the 1842 Vallejo-Casteñada Adobe, a half-block off the Plaza and restored by designer Ken Fulk. Tastings are seated, by reservation, and paired with small bites from El Dorado Kitchen. Adults only.