When Leonard Calvert and his original colonists arrived in what is now Maryland in March of 1634, they immediately set about establishing civil boundaries as they had known them in England. The seat of the first county was set up at the town site of the Ybocomico Indians. The county seat and the county itself were named St. Mary’s, in honor of Mary the Mother of Jesus, under whose protection the Maryland venture was placed.
Leonardtown has been invaded twice. The British invaded during the war of 1812 and made off with food supplies. Then, during the Civil War, a Union naval contingent came ashore and searched the houses for weapons and supplies that might be intended for shipment to Confederate forces.