Photograph: Martha Williams
Photograph: Martha Williams |

Autumn Gimlet from the Bristol (left), Orchard Old Fashioned from the Whistler (center) and Woolworth Flip from the Violet Hour (right)

Fall cocktails

Between summer and winter lies the perfect season for cocktails.

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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.

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