This paper examines the relationships between an individual’s self-reported connection to nature (CTN) and aspects of their personal well-being (PWB) and environmental awareness. Specifically, it addresses (i) the relationship between CTN and PWB; (ii) the external variables which influence trait-level CTN over a person’s life course and (iii) how individuals feel about CTN. A mixed methodology is used, with qualitative data adding depth and insight into the statistical associations recorded. The results are drawn from a sample of 222 respondents living in the City of Bath, UK. This study uncovered a significant relationship between CTN and some aspects of PWB which did not always align with research undertaken in other countries. Demographic variables, childhood experiences of nature, usual frequency of nature contact, and nature-related hobbies were all found to affect CTN. A number of barriers to CTN were also identified. Although the literature already provides considerable evidence of positive relationships between contact with nature and a range of mental and physical health benefits, the nature and mechanisms behind these relationships are not well understood, particularly for the UK population. As these associations are increasingly being used to underpin both health and environmental interventions and campaigns it is important that we better understand these relationships.