This paper presents a longitudinal mixed methods study tracking 11 children (aged 5-7 on entry), defined as disadvantaged in multiple ways, i.e. social, behavioural and economic. They attended weekly Forest School and outdoor learning sessions over three years. The study investigates the project's impact on the children in terms of their academic attainment, wellbeing and connection to nature. The children's attendance and academic attainment improved in comparison to their non-participating peers at school. The findings emphasize the importance of how social free play outdoors and relationships with a particular place can establish emotional resilience and self-regulation. The children's social development and emotional wellbeing were supported by regular outdoor sessions alongside skilled practitioners. The outcomes demonstrate important links between emotional learning and wellbeing developed in outdoor settings and academic development, raising questions about interventions for young children with disadvantaged backgrounds.