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The area has long been settled. Old Oswestry is the site of a large Iron Age hill fort with evidence for occupation dating back to the 550s BC.

The Battle of Maserfield is thought to have been fought here in 642, between the Anglo-Saxon kings Penda and OswaldOswald (c. 604 August 5, 641/ 42) was the King of Northumbria from 633 or 634 until his death. The son of AEthelfrith of Bernicia, King of Northumbria, he is best remembered as a Christian martyr. After his father was defeated and killed by Raedwald of Ea. Oswald's body was hung from a tree, which became known as "Oswald's Tree", which evolved into "Oswestry". The spring Oswald's Well is supposed to have originated where a ravenSee text Many large black birds of the genus Corvus are called ravens . Other birds in the same genus are the smaller crows, jackdaws, and rooks. With its black plumage, croaking call, and carrion-eating, the Raven was considered a bird of ill omen long b dropped one of Oswald's arms.

The Domesday BookThis article is about the 11th century census. See BBC Domesday Project for the multimedia project. Domesday Book (also known as Domesday or Book of Winchester , was the record of the great survey of England completed in 1086, executed for William the Con records a castle L'oeuvre belonging to Rainald , a Sheriff of Shropshire. The NormansThis article talks about the Norman people. There is also a city named Norman, Oklahoma in the United States. The Normans (lit. Northmen") were Scandinavian invaders (especially Danish Vikings) who began to occupy the northern area of France now known as built a castle in the 12th century11th century 12th century 13th century other centuries) As a means of recording the passage of time, the 12th century was that century which lasted from 1101 to 1200. Events Song dynasty loses power over Northern China The Kamakura Shogunate deprives the (which was reduced to a pile of rocks after the English Civil WarThe English Civil War is the period of conflict in the kingdoms of England, Scotland and Ireland between 1639 and 1651, and also refers specifically to the two wars ( 1642 1645 and 1648 1649) between the Royalist supporters of Charles I of England and the), and the town changed hands between English and Welsh a number of times during the Middle AgesThe Middle Ages formed the middle period in a schematic division of European history into three 'ages': Classical civilization, the Middle Ages, and Modern Civilization. It is commonly dated from the end of the Western Roman Empire ( 5th century) until th.

The town was still exposed to border fighting after the Civil War, and built walls for protection, but these were torn down in the 18th century, leaving only the Newgate Pillar visible today.

Notable natives of Oswestry include the composer Walford Davies, poet Wilfred Owen and writer Barbara Pym.

Attractions of Oswestry include Whittington Castle (in nearby Whittington), Shelf Bank and Oswestry School.

The local football club, Oswestry Town F.C. is one of the few English teams to compete in the Welsh football league.