Aotearoa-New Zealand’s legal, ecological and social perspectives are composed of combined Pākehā (NZ European) and Māori identities, values, perspectives and traditions. These two very different cultural perspectives are reflected in the conversations and dialogues occurring with regards to the landscape, and also in the lands forms and features itself. The separation between traditional Māori values and prevailing European developments and design approaches promotes regional landscapes that lack place and a sense of place within the wider Aotearoa-New Zealand context. South Wairarapa, in Aotearoa-New Zealand’s lower North Island, presents such a collision; the land bears the imprints of its colonising rural pedigree, and blatantly and unashamedly disregards the undeniable Indigenous Māori connection. This paper explores how landscape architecture can overlay past cultural conversations to restructure and enhance the presence of a defined regional and cultural identity and therefore promote a re-emergence of placed identity. Cultural signatures are written onto the landscape to be read and interpreted, and can be re-written, corrected and modified so to further reflect Indigenous and intrinsic connectedness with one’s landscape and its associated processes. The design, management and development of rural regional landscapes can evidence cultural values and landscape heritages while maintaining their obvious need for economic and regional prosperity, and sustainability. The apparent disconnect most modern populations have with their landscape is palpable internationally; the processes and management techniques of old are insufficient. There is a need in Aotearoa-New Zealand for an alternative approach to regional planning and design practices, which evidence our cultural pedigrees. Prominent landscape signatures should be reworked, new ones written, and the old rewritten, to create an inter-relatedness and interconnectedness between humans and ecosystems to protect past places and placements, enhance new ones, and promote the sustainable management and stewardship of the landscape.