In the mid- to late-1950s, Homer befriended Alex Jordan, creator of the House on the Rock. Homer, Alex, friend Edgar Hellum, Homer's brother Roger and members of Roger's work crew traveled to New York in March 1964 to landscape the Wisconsin Pavilion exhibit at the 1964-65 New York World's Fair. Homer had been hired by Wisconsin's Lieutenant Governor, Jack Olson, to do the outdoor landscaping and to construct an indoor waterfall.