Online photo libraries require a method to efficiently search a collection of photographs, and retrieve photos with similar attributes. Our motivation was to incorporate an existing collection of over 250 photographs of over 200 faculty members and events spanning 7 decades into a library called CS PhotoHistory that is available in hypertext and on the Semantic Web. In this paper, we identify challenges related to making this repository available on the Semantic Web, including issues of automation, modeling, and expressivity. Using CS PhotoHistory as a case study, we describe the process of creating an ontology and a querying interface for interacting with a digital photo library on the Semantic Web.