Its principal feature, a square great tower, was built during the reign of Henry II in 1160 and the castle was extended between 1166-1174.

The castle was partly slighted in 1645 and in 1646, Cromwell’s Roundheads arrived with orders to take Bridgnorth for the Parliamentarians from the garrison led by Sir Robert Howard.

[7] Following a three-week siege starting on March 31, 1646, Cromwell was successful and he ordered that the castle be demolished, but before this, they tried a strategy that failed.

A team of men led by engineer Colonel Lavington dug a 21 meters (69 ft) long tunnel into Castle Hill known as Lavington's Hole to try and blow up the gunpowder stored inside the Church of St. Mary Magdalene but the tunnel was abandoned after the Royalists surrendered to Cromwell.

[2] The Parliamentarians left it much as it is today, the stone from the castle being taken and used to repair the town's damaged buildings starting from 1647.

It was planned to be kept standing but later that year, the bailey gate was demolished by being blown up with gunpowder as it heavily obstructed traffic.