After the Norman conquest of England and parts of south Wales, Chepstow developed as an important port and trading centre within the Marcher Lordship of Striguil.

He was also responsible for the building of the Port Wall, usually dated at 1274–78, and the Town Gate; and, in 1294, for granting to his close associate, John ap Adam of Sedbury, the right to hold a regular market at Chepstow.

[1][2] The Town Gate building is square in plan, with battlements on top, and originally could be blocked with a portcullis, no longer extant.

[4] Tolls were collected at the Gate on animals and goods taken into the market place, and by people who bought livestock at the town's fairs.

A full restoration of the building took place in 1985–86, when an internal doorway apparently dating to the thirteenth century was discovered.

A plaque to mark the building's restoration, designed and decorated by local artist Keith Underwood in the style of the eroded coats of arms to either side of it, was unveiled in April 1988 by the 11th Duke of Beaufort.

[5] Road access through the single carriageway arch is controlled by traffic lights in three directions: east, north and west.

[2] On the outer side of the Town Gate, the George Hotel was originally built on this site by Margaret Cleyton in about 1620.