The active use of modern technology has affected the relationship between people and place. The “digital environment” and the “digital community” are becoming an increasingly important factor in people’s daily life, leading to a loss of belonging to a place, an entire neighbourhood, and a community. In the long run, this poses risks to the unification of values and the loss of identity. In this context, the involvement of the local community in the identification and preservation of historical heritage and defining the specific values of each site is particularly important. Thus, both the attraction of the local community to specific places and the revealed potential of local tourism are promoted. Digital placemaking enters urban regeneration as a logical approach to mixing digital and physical environments and involving the local community. Several GIS-based platforms and other tools are used to identify heritage values, both tangible and intangible. Although digital placemaking is emerging worldwide, its manifestations are closely related to specific local circumstances. The article focuses on the key characteristics and configurations of the digital placemaking tools within particular communities. The study tests digital placemaking practice in the historical districts of three cities: Taipei (Taiwan), Riga (Latvia), and Kaunas (Lithuania).