The Enology Wine Lounge sits in the lobby of Hotel E, the restored 1906 Beaux-Arts Empire Building on Old Courthouse Square. It's a loose, easygoing pour — Sonoma County wines (much of it the Wilson Artisan collection), local beer, and cheese boards, with indoor and sidewalk seating right on the Square. Come for the daily 5–7pm happy hour and its complimentary tastings; there's live music and Friday-night music bingo, too.

Not technically a tasting room, but Wilibees checks every box: a downtown bottle shop, taproom and gourmet deli where partners Vikram Badhan and Gagan Boparai pour $20 themed flights, 30-plus wines by the glass, and $5 happy-hour pours daily. Pull a bottle from the shelves, pay a small corkage, and pair it with a Brie-and-fig sandwich or a Journeyman charcuterie board. The most affordable, unfussy stop on the walk.

4th Street Cellars is a restored 1913 storefront steps from Railroad Square, where third-generation grower-winemaker John Bambury pours his Bambury collection — Bonneau, Egret and Opal Moon. Settle in by the gas fireplace, at a high-top, or out on the patio, where outside food is welcome and live music plays Thursday through Saturday. It's a Santa Rosa tasting bar built to stay open late.

Stonemason Cellars is the slate-trimmed brick room husband-and-wife team Timothy "T.J." and Francesca Elam opened a few blocks from Railroad Square, on the corner of Davis and Fifth. Working with French-born winemaker Maxime Gautier, they pour small-batch Sonoma County reds alongside a $30 five-wine flight paired with playful bites — chocolate blueberries with a red blend, caviar with a sparkling cuvée. It keeps some of the latest hours in town.