The text below is drawn from a number of places and sites on the internet. See below for main sources. It is intended to be a history for locals and visitors, not historians so it focuses on topical places and sights not the darings and doings of Owain Glyndwr! If anyone feels the need to receive acknowledgement then of course I will do so, please contact me.
There are 3 Grade 1 and 123 Grade 2 listed 'buildings' in Crickhowell, below is a very small selection.
Crucywel refers to Crug Hywel (Mound of Hywel), a reference to the prehistoric fort that occupies the flattened top of Table Mountain above the town. An alternative explanation is that 'Mound of Hywel' refers to the 13th-century Norman castle mound. The name first appears as Crickhowell in 1263.
Above is Table Mountain (to the right of the picture) and an approximation of the old castle from Wikipedia.
The Castle (Listed Grade 1)
The castle (often referred to as Aliby's castle - apparently an early governor) origins go back it seems to 1121when it was built as a motte and bailey castle by a Norman family. There is extensive history available but in short in 1400 it was reinforced ahead of the uprising of Owain Glyndŵr (an early protagonist of Welsh Independence!). His forces destroyed the castle in 1403. Much of the town has been built with the stone from the castle.
The site was gifted to the town by Gwilym C James in memory of his son who died in the first world war. The Dragon is a Grade II listed building dating from the late 1500’s. In addition to the 15 rooms the Dragon boasts a 80 seat restaurant, a function room and a bar.
Wikipedia, Britain Express, Medieval Heritage, Gatehouse Gazetteer, Ancient Monuments