The town of Montgomery lies below an outcrop of rock upon which stands the castle built by the English King Henry III around 1223. The castle is one of a number built along the line of the English /Welsh border which for many hundreds of years was an area of conflict and political tension. Just a couple of miles to the west lies Castell Dolforwyn , a Welsh castle, built just a few years after Montgomery, this area must have been one of the most militarised parts of the British Isles for many generations. Within 5 miles of Montgomery there are the remains of several iron age hill forts, a large Roman fort (probably called Lavobrinta and one of the most important Roman military establishments in Wales), Offa’s Dyke ( the huge earthwork built by the Mercian king Offa in the 8th Century AD which runs the entire length of the English/Welsh border) and one Welsh and two Norman Castles! The whole reason for all this strategic interest in the area comes from a narrow crossing of the River Severn about 2 miles from the modern site of the town. The ford at Rhydwhiman was of great strategic importance to many generations of both English and Welsh as the Severn Valley (then and now) was the major communications route into Mid Wales from England. Whoever controlled this river crossing controlled the flow of armies and trade.
The name Montgomery comes from the Norman lord who was given this area by William I after the Norman Conquest in 1066. Roger de Montgomery (1030-1094) originally came from the town of Montgomery in the Pays d’Auge in Normandy and was one of William’s most trusted followers. He was given the job of administering the vital Welsh Marches and the existing Saxon hanes were stripped of their lands in his favour. Roger and his descendants built two castles to defend the ford, the original castle at Hendomen was a wooden affair on a mound near to the crossing, the later stone castle was built about 150 years later. The modern town of Montgomery began to grow up around the newer stone castle as it provided protection and business.
Montgomery was sacked at the beginning of the 15th century by the rebel Welsh prince Owain Glyn Dwr (Owen Glendower) , the castle being at the time under the control of the Mortimer family (the hereditary Earls of March). he estates eventually came into the hands of King Edward IV after the death of the last Earl of March in 1425.
With the defeat of King Richard III at the battle of Bosworth in 1485 the royal estates including Montgomery and its castle passed into the hands of the new King, Henry VII, the first Tudor king, and a Welshman! Under Tudor patronage the castle was given to another powerful Welsh family, the Herberts, in 1541.
The castle saw action in 1644 during the English Civil War when it was first held for the King and then Parliament by the Herberts, culminating in a siege and battle during which 3000 parliamentary soldiers defeated a larger force of 5000 royalists under Lord Byron (not the poet!).
After the end of the war the castle was viewed by parliament as a danger and an order for its demolition was executed in 1649. The castle ruins are now in the care of Cadw , but it is likely that a large proportion of the older houses in the town can thank the destruction of the castle as it provided a ready source of building materials.
Montgomery was for some time the administrative centre for the old county of Montgomeryshire and hence has many old and interesting buildings in the town including an old gaol and a fine market square, the houses around which appear to be Georgian in style, but are in fact often much older with Georgian facades. There are also many examples of houses in the traditional Montgomeryshire style of half-timber (black and white) construction.
Montgomery by Gordon Cragg