Charlotte #2 at Oliver's Twist ($9)
Though this drink no longer is printed on the bar's daily menu, you can always order it—and you should. The ingredients seem to lean towards summer: there's Lillet Blanc, Crème de Pêche, and fresh lemon, but it would be a mistake to cast it off as out of season. The weight of the bourbon (it's Maker's Mark) provides balance, and welcomes the other ingredients, helping them to play nicely in this mild-flavored cocktail boasting quite the alcoholic punch.
Draper Point at The Gerald ($10)
"Don Draper meets chemistry," advertises the menu, though it's hard to imagine Draper drinking a cocktail so far from his mid-century classics. Evan Williams Bourbon and Angostura bitters are firmly in place along with Root liqueur from Art in the Age. Complexity is built up with the additions of strong black tea, apricot liqueur, orange peel, and nutmeg. This one's a thought-provoking drink, pleasing the palate while challenging the taste buds to parse out the flavors.
Quinquina Cocktail at Frank's Oyster House and Champagne Parlor ($9)
Bonal (a French wine-based aperitif) storms the simple-cocktail castle, adding complex flavors from gentian and cinchona bark—the same thing used to ward off malaria by early European arrivals in the new world. Evan Williams Bourbon steps aside to share the spotlight with Bonal in this Manhattan-inspired drink, finished with Cherry Heering to round off the bitterness.
Autumn Sweater at Essex ($10)
Drinkers go on a palate-stretching roller coaster, starting with strong bitterness, a combined effort of Averna and the house-made cherry bitters. The cherry flavor is furthered with (also house-made) cherry brandy, which, along with warming allspice dram, brings the contrasting sweet flavors. The over-arching bourbon embrace from spicy 90-proof Old Bardstown Black Label Bourbon makes this wild ride fit together in a single sip.
Pappy Flight at Vessel ($24)
Ok, it's not a cocktail, but it is required drinking. There is no better way to learn the nuances of bourbon aging than with a vertical tasting—the same bourbon, from different years—and if you're going to do that, why not start with one of the most renowned and hard-to-find bourbons in the country? At Vessel, start with the practically-newborn 12-year Pappy van Winkle, move on to the first inklings of round flavors and beginnings of smoothness in the 15-year, and finish with the caramel-scented, viscous 20-year version.