Contemporary Romania has been subject to several major social and institutional shifts that have had implications for the connectedness of humans with their environment. Four major governance eras have influenced human-nature connections: (1) formal and informal institutional governance after the World Wars and before socialism (before 1947), (2) top-down governance during socialism (1947–1989) and (3) during sovereign state governance and transition to European Union (1990–2006), and (4) multilevel governance since European Union accession (after 2007). We analyzed two cultural landscapes in Transylvania with respect to changes in human-nature connectedness. The two systems were similar at the beginning of the 20th century, but developed differently in their intensity of landscape management in the 21st century. Drawing on 41 semi-structured interviews, we examined changes that influenced landscape management and human-nature connectedness, considering five dimensions of connectedness: material, experiential, emotional, cognitive and philosophical. Material connections have weakened as a result of changes in food production and rising consumerism. Experiential and emotional connections were influenced by socio-economic and landscape management changes. Cognitive connections reflected changes in the knowledge system on the environment. Philosophical connection was influenced by changes in ideologies and globalization. Our findings highlight the central influence of social and institutional change on perceived human-nature connectedness. Understanding this influence provides important pointers for how to reconnect humanity to nature in the coming decades.