Management of digitized special collections requires ‘special’ curation; integrating Linked Open Data (LOD) into these collections also requires customized approaches different from those used for general library collections. With support from the Andrew W. Mellon Foundation, the Linked Open Data for Digitized Special Collections project is examining challenges and opportunities of LOD for three digitized special collections held at the University of Illinois. We began by transforming legacy metadata into RDF, using schema.org semantics to identify classes of entities conflated in original metadata accounts, e.g., visual artworks, person entities, theater productions, published works, and added links for linked data sources. These new LOD accounts were then embedded as JSON-LD in HTML pages to make the LOD visible to harvesting agents. To provide users more context, client-side JavaScript (relying on JQuery and Mustache.js) generates a mash-up of local descriptions and properties fetched from LOD providers like viaf.org and dbpedia.org in real-time. Links to further context are provided for person entities (playwrights, composers, actors, directors), venues (theaters), works (plays), and performances. This presentation will showcase the challenges of transforming special collection metadata into LOD and the opportunities to meet users’ needs by using LOD enrichment.