Kentucky Owl was founded by Charles Mortimer Dedman, a local pharmacist, in 1879. After marrying his wife, Dedman was given a large parcel of land on the banks of the Kentucky River, as a wedding gift from his adopted father who was a local town judge. C.M. Dedman Distillery was established here on the banks of the Kentucky River, producing "The Wise Man's Bourbon" under Distilled Spirits Plant Designation "No. 16," one of Kentucky's original distilleries and part of a booming industry.

In 2008, while aboard the ship of fellow Kentucky native and OCEARCH founder Chris Fischer, Jefferson's Master Blender Trey Zoeller got a wild idea. As he and Chris watched the whiskey swirl in their glasses, compelled by the constant rock of the waves, they pondered: what might happen to a barrel of bourbon if it were aged at sea? The rest, as they say, is history. The constant movement of the ocean and extreme temperature fluctuations as the OCEARCH traversed the globe completely transformed the whiskey. The result is a hyper-aged, darker, richer and caramelized bourbon with incredible depth and complexity. Since this discovery, Trey has sent hundreds of barrels around the world, with each voyage seeing (on average) over 25 ports, 5 continents, and 2 equator crossings.