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There are records that there was a church at this location of current St Mary's Church before the Norman conquest of Wales as it is mentioned in Domesday Book and by a charter from King John of England. However, there is nothing surviving in the current church building from that period. This is reportedly because of Augustinian canons from Llanthony Secunda visited and built the church on top of the older church that was dedicated to St Bride dating from around AD 900 at the behest of Walter of Gloucester after the construction of Caldicot Castle. The earliest part of the church is the base of the tower, which comes from the 14th century, along with the nave and chancel, which was part of an enlargement programme at the time. The tower was not fully completed until the 16th century.
In the 1850s, the 15th-century north aisle was rebuilt by Henry Woodyer, as well as most of the stained glass windows being replaced. In 1905, the chancel was refitted and many of the Victorian additions were changed.
References:Kakesbeck is one of the largest medieval fortifications in Münsterland and the oldest castle in Lüdinghausen. The imposingly grown complex originated in 1120 as a motte, a small hilltop tower castle. After numerous changes of ownership, the castle was extended onto two islands, but it was not until the 14th century that it underwent significant alterations and extensions under the von Oer family. The estate experienced its heyday in the middle of the 18th century, when it covered an area of almost one square kilometre and consisted of five further outer castles in addition to the core castle, which were secured by ramparts and moats.
The well-maintained condition of the castle today is thanks to the late Wilfried Grewing, the former lord of the castle. The foundation named after him has been particularly committed to preserving the property since 2020.