Chepstow Town Gate, City gate in Chepstow, Wales.
Chepstow Town Gate is a square stone structure topped with crenellations, positioned at the western end of High Street to mark the main entrance to the medieval town. The gate connects to remnants of the Port Wall, which extends about 700 meters through western Chepstow.
The gate was built between 1272 and 1282 under Roger Bigod's direction and controlled access to the town's market area. It also functioned as a toll collection point where traders paid fees to enter.
The western side shows two heraldic angels from 1524, added by Charles Somerset, the First Earl of Worcester, reflecting how local nobility shaped the structure to display their power and status. These carved figures reveal how important families left their mark on the town's physical appearance.
The gate sits at a central location in town and is easy to reach on foot along High Street. The open space around it provides clear views from multiple angles.
The gate witnessed intense fighting in 1648 when Royalist defenders clashed with Oliver Cromwell's troops during the English Civil War. This violent episode left its mark on the structure during a turbulent period in British history.
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