Julian P. “Pappy” Van Winkle was a travelling salesman for W.L. Weller and Sons. He created the Stitzel-Weller distillery by merging the A. Ph. Stitzel and Weller distilleries. His recipe for wheated bourbon—where wheat replaces rye as the second grain—was a massive hit. His son Julian Van Winkle II later revived the Old Rip Van Winkle brand using stocks from the distillery, which was sold in 1972 and closed by United Distillers 20 years later. Julian Van Winkle III turned to Buffalo Trace to continue production, first using the last casks of Stitzel-Weller, then Buffalo Trace's casks. Pappy Van Winkle is considered the best bourbon to have ever existed due to its recipe, quality and high age. The range includes bourbons aged from 10 to 25 years, and 13 year old and vintage rye whiskeys.

Although produced in smaller quantities than the bourbons of the same brand, Van Winkle’’s rye whiskeys are no less popular. The oldest versions are thought to have been distilled at the Glenmore distillery in Owensboro, which closed in 1993. They were matured in American oak until 2004, always for a minimum of 13 years. In 2004, the last casks were mixed in a stainless steel vat, along with Cream of Kentucky Rye from the Old Bernheim distillery, which had closed in 1988. The newest editions also contain whisky distilled at Buffalo Trace.