There has been a long tradition in the digitization and manual documentation of cultural heritage data, yet the need for indexing and retrieval that goes beyond mere bibliographic information has only recently been recognized. This chapter reports on completed work aimed at highlighting textual cultural resources that, as of yet, remain under-exploited by creating the necessary infrastructure with the support and customization of Language Technologies (LT). The ultimate goal was to promote the study of cultural heritage of the neighboring areas of Greece and Bulgaria and to raise awareness about their common cultural identity, the focus being on literature, folklore and language. To this end, a bilingual collection of literary and folklore texts in Greek and Bulgarian was developed along with a number of accompanying resources. The authors present the methodology adopted for the automatic annotation of the textual data at various levels of linguistic analysis elaborating on the Greek and Bulgarian text processing tools that are integrated in the cross-lingual search and retrieval mechanisms, and discuss issues and problems encountered in the course of the project life-cycle.