Gilpin made her earliest dated autochrome in 1908 when she was 17 years old. This photography technique had only become widely available that year, which is a testament to Gilpin's early dedication to photography. In 1915, she traveled to the Panama-California Exposition in San Diego and the Panama-Pacific International Exposition in San Francisco expositions as a companion for a friend of her mother's. At these expositions, Gilpin developed an interest in sculpture, architecture, and native cultures. She later recalled that "There was practically no art interest in Colorado Springs in those early days...I remember Harvey Young was the only painter in town and I don't think there was a sculptor. I knew "nothing" about sculpture." Gilpin took a large quantity of photographs here, some of which became the first she had published. Her photograph of the Cloister at the San Diego Exposition became her first prize-winning photograph. She won a monthly competition that was sponsored by "American Photography" magazine in May 1916.