It is believed that, in 642, the Battle of Masefield was fought there. It occurred between two Anglo Saxon kings, named Oswald and Penda. Oswald died in the battle and was then dismembered. One legend claims his arm was carried by an eagle to an ash tree and now miracle are contributed to the tree because he was a saint. It is believed the town got its name from this tree, Oswald's Tree. Oswald's Well, a spring, is said to have started where the eagle dropped his arm from the tree.
Feudal barony of Oswestry was given to a Breton knight, Alan FitzFlaad, by King Henry I. Soon after the King's accession, FitzFlaad was asked to come to England, with other Breton knights, to receive fortified Norfolk and Shropshire lands. These lands included areas that had once belonged to Ernoulf de Hesdin, who died while on crusade in Antioch, and Robert de Belleme. The duties that FritzFlaad given by the Crown, in part, was to supervise the Welsh border.
He founded, in Norfolk, the Sporle Priory. His wife was the daughter of Hesdin, Adeline. In 1131, King Stephen made their oldest son, William, was made High Sheriff of Shropshire. William then married Robert of Gloucester's niece. Walter and Simon, the couple's youngest sons, went to Scotland to in King David I's train. Walter eventually became the first High Steward of Scotland by hereditary ways with ancestry from the Stewart Royal Family.
Since the town is located so close to Wales, may of the streets and place names, are Welsh. Also, in Welsh the town's name is Croesoswallt or Oswald's Cross. The castle is recorded in the Domesday Book at being built by a Norman Sheriff of Shropshire, Rainald. It was given the name L'oeruvre, or "the work" in French. The castle was later destroyed in the English Civil War with just a pile of rocks being left.
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