Johannes "Lewis" Castleman was born in 1744 in Stone Arbria, Tryon County, in the English colony of New York. In 1765, he married Jemima Margaret Pearsall in Frederick, Virginia. He first appears in Kentucky records in 1787 in a petition that established Charlestown, and again in 1788 when Woodford County was carved out of Fayette County. He had a farm along Clear Creek, which included a tannery and a distillery that made apple brandy. He enslaved ten persons in 1810 and eighteen persons in 1819.