A fall drink is not hot: No need to invoke winter quite yet. A fall drink is not especially cool: This is tweed weather, no matter how warm Tom Skilling predicts the temps will be. A fall drink is the Woolworth Flip at the Violet Hour (1520 N Damen Ave, 773-252-1500): Buffalo Trace bourbon, laced with notes of cherry and vanilla (from Carpano Antica sweet vermouth), bitter chocolate (Cynar), sarsaparilla and sassafras (from housemade root-beer bitters), and shaken with a whole egg. “It looks like a rather bizarre drink,” says the Violet Hour's Toby Maloney. But the idea is simple: “It’s all the flavors you could find at a soda fountain a hundred years ago.”
Sometimes a little tweak is all it takes. At the Whistler (2421 N Milwaukee Ave, 773-227-3530), Paul McGee adds one part Leopold Bros. New York Apple Whiskey to three parts Old Overholt rye, and with a dash of Angostura bitters, there you have it: the Orchard Old Fashioned. At the Bristol (2152 N Damen Ave, 773-862-5555), Debbi Peek loads a classic gimlet (Plymouth gin, fresh lime juice and simple syrup) with fresh basil and tons of Bitter Truth Aromatic and Jerry Thomas bitters, giving it “lots of head-spice flavor like cinnamon and clove,” Peek says. “Being a gimlet, it’s not heavy,” she adds. Rather, the Autumn Gimlet is wistful. Smelling the basil recalls the last vestiges of summer; drinking it is an affirmation of the pleasures of fall.