Esquire Tavern: Classic, Straight Up

Oldest bar on San Antonio's River Walk serves up a cowboy-class/speakeasy vibe

Time seems to stand still at The Esquire Tavern. Opened in 1933 to celebrate the end of Prohibition, The Esquire remains the oldest operating bar on the River Walk and brings a touch of cowboy class to its swanky speakeasy atmosphere.

Mosey up to Texas’ longest wooden bar (108 feet long!) and throw back a house cocktail ... or three. There is a wealth of local beers on tap, including those from hometown brewery Ranger Creek, along with a selection of creative, handcrafted cocktails. Try the Capone’s Revolver, a spirited combination of rye whiskey, coffee liqueur and Fire & Damnation Bitters, or the Buchanan Daisy: a classic Hemingway daquiri laced with the herbal liqueur known as yellow chartreuse.

When happy hour spills over, request a spot on the patio overlooking the River Walk. The menu’s varied flavors reflect the bar’s locale, mixing Southern staples and Mexican favorites. Appetizers like fried pickles and deviled eggs are complemented with diverse main courses, including a scrumptious chile relleno and a hearty bison burger. Stick around for the chocolate mousse or fried apple pie, served with a scoop of Justin’s vanilla bean ice cream.

155 E. Commerce St., 210.222.2251