Old Settler Bourbon's history echoes back to the post Civil War whiskey distilling enterprise of Edward J. Curley. Born in Massachusetts, he came to Kentucky as a Union Soldier and, following confederate surrender, began distilling whiskey alongside two partners in an area known as Boone's Knoll. By the late 1860s, Curley’s Blue Grass Distillery had been constructed and began producing whiskey the old fashioned way, with a recipe known only to him, that made use of local spring water, a copper kettle, and its own on-site cooperage. He operated the Blue Grass Distillery for nearly 30 years before being forced to sell at the age of 53. What his future life may have held is shrouded in the mists of time.

The distillery changed hands and continued to produce rye whiskey under new owners until it was shuttered by prohibition. After prohibition's repeal, the distillery reopened with the name Kentucky River Distillery and kept up production until the 1960s when it was purchased by Canada Dry. A fire destroyed much of the property, and what remained of the warehouses were leased to Seagrams. Many years later, any undamaged stone buildings that remained of the distillery were leased to the producers of Wild Turkey.

In 2019, the trademark for Old Settler was purchased by Brindiamo Group LLC and their production began at Boundary Oak Distilling in Kentucky near Fort Knox. A minimum of 12 year old bourbon was sourced for this special release (the original product was 5 years old).