In recent years, riding schools have opened their activities for younger children. The activities consist of riding, but also chores in the stable (Thorell, 2017; Hedenborg et al, 2021). Equestrian sport is not alone in offering activities for this age group. Other sports have also opened the doors for the younger children (Lindroth, 1991; Hedenborg, et al, 2020). Activities for this age group are also offered by commercial actors (Karlsson, 2022). Although more and more activities are offered, research on what goes on in these activities and how they are experienced by both parents and children is scarce (Hedenborg & Fransson, 2011; Calero, Beesley & Fraser-Thomas, 2018; & Safari, 2018; Harlow et al., 2018). In this article, the aim is to deepen the understanding of riding school activities for preschool children in Sweden and Norway by analyzing riding instructors’ and accompanying adults’ the perceptions of the activities. To deepen the understanding of the challenges that riding instructors and accompanying adults face in riding school activities for the younger children, we use the interpretive framework ‘dilemmatic spaces’ (Fransson & Grannäs, 2013). In previous research, ‘dilemmatic spaces’ have been used to increase understanding of the complexity of teachers’ work. But the interpretive framework has also been used in other fields. Childhood researcher Magnus Kilgers uses ‘dilemmatic spaces’ in a study that shows how fathers juggle between what is expected of fatherhood and coaching in sports (Kilger 2020). Based on a source material consisting of 21 semi-structured interviews with representatives from riding schools and parents, and ten observations from six different riding schools, we have identified the following ‘dilemmatic spaces’: ‘Accompanying adults are both a requirement and a challenge’ and ‘Knowledgeable mothers are an asset but mustn’t be pushy’.