Earlier sites The first fortification at Longtown was a
Roman fort, close to a
Roman road that ran along the borderlands. The fort was square, and protected by a ditch and a timber palisade. The Roman defences were reinforced, probably in 1055, after a Welsh attack on
Hereford. Following Welsh attacks, Walter abandoned Pont Hendre and instead started to build a castle at Longtown, on the site of the old Roman fort. Longtown Castle was designed as a
motte and bailey castle, on high ground alongside the
River Monnow. More defensible sites on higher ground existed nearby, but this location was strategically well located close to the river, an important transport route. It had a high motte and an unusual rectangular bailey design around by , divided into three parts, two baileys in the west and one in the east, each capable of being defended independently and enclosing around in total. The 12th-century castle was built primarily of timber with at least some stone in its design, but this stone was then reused when the castle was rebuilt in the 13th century. Two circuits of earthworks to the north and south of the castle, possibly with wooden
palisades, enclosed the early settlement of Longtown. The region was troubled for the rest of the century, with revolts by the local Welsh against Anglo-Norman rule. The de Lacys lost their lands in the region after conspiring against
William II, but around 1148, Gilbert de Lacy regained the estates. The stone keep was constructed in the form of a circular great tower, with walls thick and three turrets spaced evenly around the outside and a hall on the first floor. This circular design is particular to the Welsh Marches, and is also seen at
Skenfrith and
Caldicot. The reason for this choice is unclear, as it appears to have carried few military advantages. The stonework is made up of
sandstone rubble with cut
ashlar detailing; the walls are around thick, but the keep's foundations are extremely shallow. An inner gate to the western baileys was built to a simple design with two small turrets, and seems to have been fitted with a portcullis, while a thick wall encircled the rest of the inner western bailey; another stone wall seems to have protected the outer half of the bailey. Inside the inner western bailey appears to have been the castle's great hall and other service buildings.
Expansion and decline The de Lacy family controlled Longtown Castle until
Walter de Lacy's death in 1234.
John Fitzgeoffrey then acquired the castle, during a period of increased conflict and tension between the Welsh princes
Llywelyn the Great and
Dafydd ap Llywelyn and the English marcher lords. The castle reverted to the de Lacy family and became part of the inheritance of Margery (or Margaret) de Lacy, daughter of Gilbert de Lacy, who had predeceased his father Walter de Lacy, Lord of Meath, and his wife Isabel Bigod, daughter of Sir
Hugh Bigod, 3rd Earl of Norfolk. Marjory married John de Verdun of
Alton, son of
Theobald le Botiller and
Roesia de Verdun. The de Verduns struggled with local lawlessness and the Welsh revolts which continued until the end of the century. The
Nevilles acquired the property in the 15th century and it remained in the control of the Lords of
Abergavenny until the 1970s. It is unclear if the castle and town played any part in the
English Civil War between 1642–45, although cannonballs from the period have been discovered within the castle. Stones from the castle were used for local building work by the 17th century onwards, and by the 18th century a house and shop had been constructed in the eastern bailey of the castle, along with a yard and garden. It was in a poor condition and extensive restoration work was carried out, including the removal of many of the buildings that had encroached on the walls. In the 21st century, the central parts of Longtown Castle, including the ruined keep, the internal gatehouse and fragments of the curtain wall, are maintained by
English Heritage as a tourist attraction, although the wider earthworks lie on common land. In 2016, the Longtown and District Historical Society obtained
Heritage Lottery Funding for a community archaeology project to research Longtown Castle over the next two years. The castle is protected as a
scheduled monument. ==See also==