From Seven Cutters to Seven Hundred Boats The Cowes story began on 10 August 1826, when seven cutters gathered off Cowes Castle to compete for a gold cup worth the princely sum of £600 — a fortune at the time. There were no racing rules, no handicaps, and no race committees — just wind, tide, and nerve. At the firing of the start gun, they weighed anchor and tore off down the Solent.