Born in 1799 in North Carolina, James Washington Cockrum purchased land in Gibson County in 1818 and, with Jacob Warrick Hargrove, laid out the town of Oakland, now Oakland City, on January 15, 1856. Cockrum and his son William Monroe Cockrum, along with sympathizers in Warrick, Gibson, and Pike counties, aided enslaved blacks seeking freedom. James W. Cockrum's barn, originally located on this property, was used to hide freedom seekers. The Underground Railroad was a widespread network of diverse people in the nineteenth century who aided slaves escaping to freedom from the southern U.S. Cockrum died on November 19, 1875.