A metropolitan area has yearn been settled. Old Oswestry is the site of the big Iron Age hill fort with evidence for occupation dating back to the 550s BC.

A Battle of Maserfield is thought to have been fought on this button within 642, between the Anglo-Saxon kings Penda and Oswald. Oswald's person was hung from either the tree, which became called "Oswald's Tree", which evolved into "Oswestry". A spring '''Oswald's Swell''' is supposed to use at times originated in which the raven dropped one of Oswald's arms.

Offa's Dyke runs nearby to the west.

A Domesday Book records a castle 50'body of work belonging to Rainald, a Sheriff of Shropshire. A Normans built a castle in the 12th century (which was reduced to a pile of rocks when a English Civil War), & a town changed mitts between English and Welsh a total of days in the period of the Middle Ages.

A town was however involved to border combat fallowing a Civil War, & built bulwarks for protection, however these were raze in the 18th century, leaving just a Newgate Pillar seeable now.

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

A previous local football club, Oswestry Town F.C., was one of the few English teams to compete in the Welsh football league. Oswestry Town folded due to fiscal difficulties around 2003 and merged with Total Network Solutions F.C. of Llantsaffraid, a village eight miles (13 km) away on the Welsh side of the border. TNS is building the recently ground withinside Oswestry which is scheduled to open in 2005.

Notable Oswestrians

Walford Davies, composer Alexander Macmillan, 2nd Earl of Stockton, Chairman of Macmillan Publisher Ltd. Wilfred Owen, poet Barbara Pym William Henry Griffith Thomas George Williams, Michigan State Senator Ian Woosnam, golfer