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The late 13th and early 14th century probably saw the peak of Chester's prosperity in the Middle Ages. Though there was a corn market in Eastgate Street by the 1270s, and though some corn was undoubtedly grown in the county and by the citizens themselves in the town fields, considerable quantities of wheat and barley had to be brought in from further afield, principally Ireland. The grain was not simply for home consumption: the city also acted as a centre for distribution throughout its region. Although trade with the native Welsh was suspended during Edward I's campaigns, such disruption was more than counterbalanced by the citizens' provisioning of the English armies.
Edward I used Chester as his base for military campaigns against North Wales in 1277 and 1282, and hundreds of masons, carpenters and laborers employed to build the "Welsh" castles had their winter billet in Chester. The city was at the height of its prosperity and wealthy merchants could embark on a building boom with some of the country's most highly skilled craftsmen on hand. The Rows seem to have been largely in place by c1350.
Trade rose to a peak during the campaign of 1282-3, when foodstuffs, including peas, beans, wine, salmon, cheese, and salted meat as well as corn, flowed through Chester in quantities which far exceeded those from any other province apart from Ponthieu. With the establishment of peace Chester resumed its wider distributive role. The extremely high tax income of the Dee Mills throughout the 13th and earlier 14th century perhaps reflected toll income resulting from Chester's role as an entry-port for wheat, oats, barley, and malt.
In the reign of Edward II, when they were first recorded in detail, tolls were levied on the goods of 'foreign' merchants as they entered and left the Chester, the citizens themselves being exempt.
- At the Eastgate, the principal entry for landborne traffic and the only gate at which tolls could be paid in cash, there was a tariff for wool, salt, coal, timber, 'long boards', bark for tanning, turf, knives, cups, dishes, and tankards. Merchandise produced within Cheshire, including corn, malt, lead, iron, steel, and livestock, was exempt.
- At the Northgate the serjeant took toll on a wide variety of sea fish and shellfish, ale, fruit, sheep, timber, shingles, coal, firewood, and turf.
- At the Bridgegate tolls were taken on cattle brought in from Wales, fish and shellfish of various kinds, hops, nuts, firewood, turf, coal, timber, shingles, laths, bark for tanning, knives, cups, and dishes. Levies were presumably also made at the two adjacent gates, the Shipgate and the Horsegate, for which the serjeant of the Bridgegate was also responsible.
- The commodities which passed through the Watergate were similar, and included barley, various kinds of fish, coal, cups, dishes, and knives.
In 1361 the citizens of Chester claimed that they lived by trade. In the later Middle Ages, however, the port suffered from facing west, away from the Continent, and also perhaps from the silting of the Dee estuary, as was frequently alleged. Ships with very heavy cargoes, such as wine and millstones, unloaded at anchorages in Wirral, the goods then being transferred to smaller craft or carts, but the city's own harbour at Portpool handled fish, Welsh slates, woollen cloth, hardware, and malt, and at high tide the smallest vessels could reach the New Tower (Watertower) at the north-western corner of the city walls.