Stir ∙ 3 min ∙ 27.1% ABV ∙
The Chocolate Old Fashioned stirs cherry bourbon with Calvados and chocolate syrup — a dessert-leaning riff on the classic. Rich cocoa coats the palate first, cherry-inflected bourbon and apple-brandy warmth building underneath, finishing dry with a faint bitters snap.
The Chocolate Old Fashioned is a modern flavored variation of the Old Fashioned, one of the oldest named cocktails in America. The Old Fashioned's own history is disputed: cocktail writers trace the underlying style of spirit, sugar, water, and bitters to the early 1800s, with the term "old-fashioned cocktail" appearing in print by 1880 and the earliest known recipe under that name published in Chicago in 1888. A widely repeated club legend, first put in writing by Waldorf-Astoria bar manager Albert Stevens Crockett in the 1930s, credits a bartender at the Pendennis Club in Louisville, Kentucky, with inventing the drink for bourbon distiller Colonel James E. Pepper sometime between 1889 and 1895, after which Pepper is said to have popularized it at the Waldorf-Astoria in New York. Cocktail historians, including David Wondrich, reject this Pendennis Club origin story as a myth, since recipes for an "old-fashioned whiskey cocktail" were already circulating decades earlier in Chicago, Cincinnati, and New York. Despite the dispute, Louisville named the Old Fashioned its official city cocktail in 2015. The Chocolate Old Fashioned itself has no separately documented creation story; it is simply a contemporary twist on this classic template that swaps in chocolate, typically as a liqueur, syrup, or bitters, for part of the sweetening in place of the plain sugar of the original.