In Holmes' many trips by steamboat between New York and New Orleans in the early 1850s, the businessman frequently journeyed by the Ohio River and was attracted to Covington, Kentucky, as a rest stop. Holmes bought land in the Kenton County area known as Buena Vista; in 1866, he began to build the home of his dreams. He named the three-story, English-gothic castle as Holmesdale. The 32-room mansion was built on about . Holmes divided his time between Holmesdale, a home in France, and an apartment in New Orleans.