1586 – Sir Francis Drake and over 1,000 men left St. Augustine after burning the settlement to the ground on this date. The raid was part of a much larger Anglo-Spanish War between England and Spain which spilled over into the new world. Although the city was destroyed and much of their supplies had been plundered by Drake’s forces, the people of St. Augustine were able to slowly rebuild with the help of the Spanish government, and eventually began construction on a permanent stone fort after subsequent attacks from others, now known as the Castillo de San Marcos.