Our prevailing image of Astley’s is the 1808 Thomas Rowlandson-Auguste Pugin engraving in Rudolph Ackerman’s The Microcosm of London in which a rider, standing upright on the back of a capering horse (as a clown-to-the-horse stands by) performs before a packed auditorium of fashionable ladies and gentlemen. Our account precedes that moment by more than four decades when, in 1759, the teenage Philip Astley, escaping family poverty, enlists in the Earl of Pembroke’s 15th Light Dragoon regiment. Sent for cavalry training to Wilton House (near Salisbury in Wiltshire) and in the Earl’s indoor manège, young Astley was trained in military equitation and use of cavalry weapons by Pembroke, Col. George Eliot, and Pembroke’s riding master Domenico Angelo, the trio advocating and enforcing a style of riding which sharply differed from conventional cavalry horsemanship. This style and the very choice of horses on which he was trained would thereafter be the basis for Astley’s great skill, his feats in battle, the horses employed in his arenas, and the approach to riding which he would demand of his actors and performers. Astley returned a war hero from the Seven Years’ War, rising to the rank of sergeant major and displaying exceptional equestrian skills. His feats in battle earned the patronage of George III which Astley was to repeatedly exploit. Discharged c .1768, Astley, now married, busked in the public parks, showing some of his trick-riding feats before opening a riding school in Lambeth. In this essay, we discuss how the vogue for riding amongst the emerging middle classes made the teaching of equitation a profitable enterprise, and we look closely at Astley’s riding school, his pupils, and the displays of horsemanship and other acts demanding physical skills at that school. These performances, initially in an outdoor venue subject to the vagaries of weather and to the hostilities of the Royal Patent holders, led to Astley’s enclosed Royal Grove Theatre and, after a 1794 fire, an even grander structure on the same site, just south of Westminster Bridge. We identify how Astley acquired his patent.