Equestrian media is showing an increasing interest in the impact of mental health on performance and general wellbeing of equestrian athletes. This study explores the awareness of mental health difficulties and psychological wellbeing within equestrian sport from the perspectives of equestrian athletes, instructors/coaches and parents. The exploratory nature of the research offered opportunity to use a dual approach including e-surveys and semi-structured interviews. Analysis of the qualitative data identified five key themes (Emotional Wellbeing in Balance; Emotional Wellbeing Imbalance; Wellbeing Imbalance—Impact on Equestrian Sportspeople; Impact of Equestrian Sport on Wellbeing; Regaining Balance) and 22 sub-themes. The findings determine a compelling need for education, promotion of sharing experiences, facilitation of specialist (clinical and sport) professional training and intervention as well as a review of regulations from equestrian Governing Bodies.