• Oswestry - 'Oswald's Tree'. The name Oswaldestre did not appear until 1272.

The area has long been settled. Old Oswestry is the site of a large Iron Age hill fort with evidence of 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 Oswald. Oswald was killed in this battle and was dismembered; according to a legend, one of his arms was carried to an ash tree by a bird, an eagle, and miracles were subsequently attributed to the tree (as Oswald was considered a saint). Thus it is believed that the name of the site derived from a reference to "Oswald's Tree". The spring Oswald's Well is supposed to have originated where the bird dropped the arm from the tree. Offa's Dyke runs nearby to the west.

Alan FitzFlaad (d. c1114), a Breton knight, was granted the feudal barony of Oswestry by King Henry I who, soon after his accession, invited Alan to England with other Breton friends, and gave him forfeited lands in Norfolk and Shropshire, including some which had previously belonged to Ernoulf de Hesdin (killed at Antioch while on crusade) and Robert de Belleme.

Alan's duties to the Crown included supervision of the Welsh border. He also founded Sporle Priory in Norfolk. He married Ada or Adeline, daughter of Ernoulf de Hesdin. Their eldest son William was made High Sheriff of Shropshire by King Stephen in 1137. He married a niece of Robert of Gloucester. But two of their younger sons, Walter and Simon, travelled to Scotland in the train of King David I, Walter becoming the first hereditary High Steward of Scotland and ancestor of the Stewart Royal Family.

The town, being very close to Wales, has many Welsh street and Welsh placenames and the town's name in Welsh is Croesoswallt, meaning Oswald's Cross. The Domesday Book records a castle being built by Rainald, a Norman Sheriff of Shropshire: L'oeuvre (meaning "the work" in French) (which was reduced to a pile of rocks during the English Civil War), and the town changed hands between English and Welsh a number of times during the Middle Ages. In 1149 the castle was captured by Madog ap Maredudd, and remained in Welsh hands until 1157. Later, Oswestry was attacked by the forces of Welsh rebel leader Owain Glyndwr during the early years of his rebellion against the English King Henry IV in 1400; it became known as Pentrepoeth or 'hot town' as it was burned and nearly totally destroyed by the Welsh. It eventually became known as Oswald's Tree in English, from which its current name is derived.

Oswestry - Historic buildings in the town centre, October 2008.In 1190 the town was granted the right to hold a market each Wednesday. After the foot and mouth outbreak in the late 1960s the animal market was moved out of the town centre. In the 1990s, a statue of a shepherd and sheep was installed in the market square as a memorial to the history of the market site. With the weekly influx of Welsh farmers the town folk were often bilingual. The town built walls for protection, but these were torn down by the Parliamentarians after they took the town after a brief siege on 22 June 1644, leaving only the Newgate Pillar visible today.

Park Hall, a mile east of the town was one of the most impressive Tudor buildings in the country. It was taken over by the Army in 1915 and used as a training camp. On 26 December 1918 it burnt to the ground following an electrical fault. The ruined hall and camp remained derelict between the wars. For decades following World War 2, Oswestry was a prominent military centre for Canadian troops, later British Royal Artillery and latterly, a very successful training centre for 16-18 year old Infantry Junior Leaders. This long and proud military connection came to an ignominious end in the mid-1970s, shortly after some local licensed wildfowlers were shot by the young military guard one winter's night, mistaken for an attacking IRA force, as the locals discharged their shotguns at some passing ducks. The area previously occupied by the Park Hall military camp is now mainly residential and agricultural land, with a small number of light industrial units.

Attractions in and around Oswestry include: Whittington Castle (in nearby Whittington), Shelf Bank, and the Cambrian Railway Museum, located near the former station. The town is famous for its high number of public houses per head of population; there are around 30 in the town today, many of which offer real ale. A story incorporating the names of all of the pubs once open in Oswestry can be found hanging on the walls of The Oak on Church Street.

St Oswald's Church, the parish church is almost 1,000 years old, with the Norman tower dating from 1085. There is a new window in the East nave designed by prestigious stained glass artist Jane Grey in 2004. There are also 12 other churches in the town, including a Welsh Presbyterian in Victoria Road.