Criccieth Castle a distant relation of Llywelyn ap Gruffudd, began an uprising against English rule that spread quickly through Wales. Several English-held towns were razed and Criccieth (along with Harlech Castle and Aberystwyth Castle) were besieged that winter. Its residents survived until spring when the castle was resupplied. In the 14th century the castle had a notable Welsh constable called Hywel ap Gruffydd, known as Howell the Axe, who fought for Edward III at the Battle of Poitiers in 1356. The castle was used as a prison until 1404 when Welsh forces captured the castle during the rebellion of Owain Glyndŵr. The
Gruffudd ab Owain Glyndŵr Gruffudd, and another rebel Captain Rhys Gethin. They were defeated by Prince Henry of Monmouth, later to become King Henry V or possibly John Talbot, 1st Earl of Shrewsbury. The exact place and date of this battle is subject to dispute, but the Annals of Owain Glyndwr call it the Battle of Pwll Melyn, near Usk. The result appears to have been a major Welsh defeat, the capture of Gruffudd ab Owain Glyndŵr, and the deaths of Tudur and Rhys Gethin. Before being taken to the Tower of London he was first imprisoned at Nottingham. He was sent from there