This paper addresses sustainable development processes based on biocultural heritage, sense of place, and socio-cultural innovation and inclusiveness in the rural context, particularly focusing different scales of endogenous/neo-endogenous rural regeneration processes. Ethnographic and grounded case studies allow a critical analysis of different forms of rural development from a multidisciplinary perspective based on old and new rurality, rural and local communities’ participation, resilience and regeneration processes, sense of place, belongingness, and “restanza”. The three cases are situated in three areas of Italy: the ecomuseum of pastoralism in Pontebernardo in the northern region of Piedmont as a driver of local shared development pathways; the municipality of Castel del Giudice, in the Central-Southern region of Molise, enabling different and integrated local regeneration actions; and the Association “Casa delle AgriCulture”/Green Night Festival in Castiglione d’Otranto in the Southern region of Puglia as a performative opportunity to define innovative and transversal as well as community-oriented activities. In these contexts, different local regeneration programs were applied in order to provide a critical evaluation of the knowledge and practices of sustainability in terms of their entanglements with biocultural heritage and socio-cultural innovation. The present analysis insists on the impact of biocultural heritage in regeneration processes in rural regions and endogenous/neo-endogenous factors in rural sustainable development.