At the ripe young age of nineteen, Henry McKenna left his native Ireland to make his mark in the new world. McKenna was a wanderer, eventually arriving in Kentucky, where he toiled as a road worker under the sweltering summer sun. He eventually established his own grain mill in Fairfield, Kentucky. In 1855 McKenna began using the mill's excess grain to produce his now famous double distilled Bourbon. To McKenna, making Bourbon was an art. Starting with less than a barrel a day, he focused solely on the quality of the spirit.

McKenna's Double Distilled Kentucky Straight Bourbon was quickly recognized as the best and purest ever made. Throughout the latter part of the nineteenth century and the early 1900s, McKenna Bourbon was savoured by a privileged circle of American Whisky enthusiasts who demanded nothing but the best. Following the dry days of Prohibition, word of the double distilled, extra smooth Bourbon quickly spread, and urban bars snapped up all he could supply. Capacity was pushed to twenty barrels per day, but demand still outstripped supply. McKenna remained adamant that his Bourbon would not be compromised by mass production. It remains to this day, one of the great Kentucky Whiskys