This chapter offers theoretical considerations and reflections on technological solutions that contribute to digitally supported documentation, access and reuse of localised heritage content in public spaces. It addresses immaterial cultural heritage, including informal stories that could emerge and be communicated by drawing hyperlinks between digitised assets, such as songs, images, drawings, texts and more, and not yet documented metadata, as well as augmenting interaction opportunities with interactive elements that relate to multiple media stored in databases and archives across Europe. The aim is to enable cultural heritage to be experienced in novel ways, supported by the proliferation of smartphones and ubiquitous Internet access together with new technical means for user profiling, personalisation, localisation, contextawareness and gamification. The chapter considers cyberparks as digitally enhanced public spaces for accessing and analyzing European cultural heritage and for enriching the interpretation of the past, along with theoretical ramifications and technological limitations. It identifies the capacities of a proposed digital environment together with design guidelines for interaction with cultural heritage assets in public spaces. The chapter concludes with describing a taxonomy of digital content that can be used in order to enhance association and occupation conditions of public spaces, and with discussing technological challenges associated with enriching public spaces with localized cultural heritage material.