Calraet probably trained with Aelbert Cuyp, whose works are also well represented in Dulwich’s collection. Due to the fact that Calraet signed his works with the same initials as his master's (although with a rather distinct cypher), Calraet’s pictures were regularly misattributed to Cuyp - in this case up until 1953.
The theme of the riding school was also inspired by Cuyp, as were the poses of some of Calraet’s horses. The chestnut horse in this painting is nearly identical to one which appears in Cuyp’s An Evening Ride near a River, also in Dulwich’s collection.