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School-based outdoor learning can offer a valuable means to reach a wider range of children than through community-based health and wellbeing projects as the majority of children regularly attend school. This is especially important now as the time children spend outside has decreased over recent years with access most restricted for low socioeconomic and minority ethnic groups and the COVID-19 pandemic has placed increasing pressures on how to maintain educational outcomes and health. The challenges to contemporary health and wellbeing include both physical and mental health, with rising levels of childhood obesity and declining mental health in youth. In this chapter, we describe research that has looked at pupils’ physical activity levels during the school day, and children’s and teachers’ wellbeing as a result of school-based outdoor learning. We reflect on how these key outcomes—health and wellbeing—may best be supported for this and future generations.