Horseback riding is a unique activity for Rumsey Hall students to participate in during the fall and spring terms. Classes take place at Fox Crossing Equestrian in Morris Connecticut, one of Litchfield County's premiere riding and boarding facilities since 2008. The activity is open to students in the IVth, Vth, VIth, and VIIth Forms regardless of previous riding experience.

Horseback riding has been shown to increase mental health by reducing stress and encouraging relaxation. While Rumsey students become proficient at walking, trotting, and cantering in small groups, they are also training their minds and bodies to interact with an animal in a responsible way.

Riders strengthen their base of support and help stabilize their hand and arm positions, all the while focusing their minds to settle down from the digital world they are accustomed to. They learn how to effectively monitor their horse's pace and practice eye control. Riders develop techniques that enable them to practice mindfulness while increasing the awareness of their sense of self in relation to the natural world around them.