On May 21, 1729, John Wolmer made his last will and testament, bequeathing the bulk of his estate – 2,360 pounds sterling – for the foundation of a free school in whichever parish he happened to die. Wolmer’s Boys School was officially founded on that day, making it the oldest school in the Caribbean. However, it took a few years of amendments and conferences between the House of Assembly and the Council before a law was passed giving effect to the will, and the Wolmer’s Trust which would manage the affairs of the school was established in 1736.
The school was established in downtown Kingston on Church Street, but suffered significant damages in the 1907 earthquake. It was relocated to its present site north of the former Kingston Race Course, which is now the National Heroes Park. The original Wolmer’s School site is now a parking lot and vendors’ arcade beside the Kingston Parish Church. In 1896, the institution was separated and independent heads appointed for the boys’ and girls’ schools.