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In the 19th century a shipbuilding industry developed, and the town was also known for the production of clocks, bells, and grindstones.
In 1840 leaders of the Chartist insurrection in Newport were transported from Chepstow to Van Diemen's Land.
The port's trade declined after the early 19th century, as Cardiff, Newport and Swansea became more suitable for handling the bulk export of coal and steel from the Glamorganshire and Monmouthshire valleys.
However, shipbuilding was briefly revived when the National Shipyard No. 1 was established during the First World War and for a short period afterwards, when the first prefabricated ships, including the War Glory, were constructed there.
The influx of labour for the shipyards, from 1917, led to the start of " garden suburb " housing development at Hardwick ( now known locally as " Garden City ") and Bulwark.
The shipyard itself became a works for fabricating major engineering structures.
From 1938, Chepstow housed the head office of the Red & White bus company, on Bulwark Road.

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