This spurred the landowners to develop extensive city walls, enclosing a large part of the settlement into what is now termed the "old town." Although the actual wooden gates into Tenby no longer exist, the Five Arches at the edge of old town give an insight into what the merchants would have marvelled at as they entered.
During the Wars of the Roses Henry Tudor, the future King Henry VII of England, sheltered within Tenby before sailing into exile in 1471. Consequently, in the Late Middle Ages, Tenby was awarded various royal grants which financed the maintenance and improvement of the town walls and the enclosure of the harbour. The harbour during this period became a busy and important national port. Originally based on fish trading, traders sailing along the coast to Bristol and Ireland, and further afield to France, Spain and Portugal. Exports from Tenby included wool, skins, canvas, coal, iron and oil; while in 1566 Portuguese seamen landed the first oranges to be brought to Wales.
Two key events caused the town to quickly and permanently decline in importance. Firstly, in the English Civil War, the town declared for Parliament and resisted two attempts by Charles Gerard, 1st Earl of Macclesfield to capture it for the King, Charles I. In 1648, the Royalists captured the castle for ten weeks before surrendering to Colonel Thomas Horton, who welcomed Oliver Cromwell to the town shortly afterwards. In the following year, 1650, a plague epidemic
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