Welsh names frequently have different meanings and origins. This adds to the difficulty in doing genealogy for those of us not familiar with the "landscape" surrounding such words. For example, the word Oswestry can mean a borough, a market town, a parish, a hundred, or a lordship. When the name Oswestry is given today, you automatically assume it is referring to the town located in the county of Salop. [ 17 miles N.W. from Shrewsbury, and 180 mile N.W. from London.] However, when listed in a historical document, it may mean any one of the items listed above. Thus, determining these distinctions may make the difference in shaking the correct family tree branches!
First called "Maes Usswalt" after Ussa, the son of Cunetha Wledic (Cunedda, known as Cunedda "The Lion".] , it became called Maserfield. This meaning "the field" of Ussa. On August 5, 642 AD, a battle was fought here between Penda [pagan king of Merica 632-654 AD], and Oswald [Christian king of Northumberland]. The story goes that Oswald was slain near a tree, and his body was divided, and fixed to three crosses. [ Derision of Christianity by a Pagan king!] The Welsh called it "Croes Oswald" and a monastery was formed coming to be called "Oswald's Cross" = Oswestry! It was annexed to the Kingdom of Mercia following Offa's Dyke, and a castle was built 1149 AD by Madog ap Meredydd. By this time "Oswestry" had become a "borough" [Norman influence], a "market town" [trade influence], a "parish" [Church influence], a "hundred" [state influence], and a "lordship" [monarch influence]! Thus, "The Lordship of Oswestry", was located as "The Hundred of Oswestry", in the "Parish of Oswestry", as a "borough" and "market town". The "Hundred of Oswestry" contain the townships of "Llan-forda", "Maesbury", "Middleton", and "Weston".
Wow! Who would have thought that the name Oswestry could have such a meaning?
A helpful reference is: A Topographical Dictionary of England, by Samuel Lewis, Vol. II, p. 458-460. [Originally published in four volumes, London, 1831.]