Montgomery is a small town that nonetheless has been of strategic importance for centuries owing to its position close to a narrow crossing on the River Severn. Whichever group held this region on the Welsh-English border controlled the passage of armies and trade into and out of Wales. This is one of the most fortified regions in Britain, with several iron age hill forts (NPRN 92480), a Roman fort(NPRN 94012), Offa's Dyke (NPRN 92494) and several castles, including Montgomery Castle (NPRN 92482), built c.1223, around which the market town of Montgomery developed. The town was given borough status on 15 February 1227, at which time the Parish Church of St. Nicholas was begun (NPRN 152865), and the town walls (NPRN 306412) were constructed.
The town was the scene of frequent contests between the Crown and Llewellyn the Great, and was sacked in the early fifteenth century by Owain Glyndwr, but was rebuilt and continued to flourish as a trading centre. In 1649, despite the town surrendering to the Parliamentarians, an order was passed that the castle be destroyed. This has, however, contributed to the appearance of the town, many buildings in which were constructed from materials plundered from the ruined castle. It includes cobbled streets and timber-frame houses, with traditionally placed central Town Hall (NPRN 32055) which also served as the Market Hall.

Source: Lewis, A Topographical Dictionary of Wales, 1833

K Steele, RCAHMW, 20 January 2009