During no period of the English rule in France were the ties which united England and Gascony more numerous or more powerful than in the reign of Edward III For nearly two centuries their intercourse had been developed by subjection to a common ruler, and the opening of the Hundred Years' War greatly contributed to the same end by necessitating the residence of increasing numbers of English officers in the Duchy, by making it a base for hostilities and a depôt for supplies. The trade with Gascony moreover was not at this period confined to imports, or it would have been less lucrative than it was English ships on the outward journey, and those of Gascons returning carried great quantites of corn, wool, cloth, and fish.
In Toulouse scarcity of corn was very frequent, and could only be remedied by obtaining freedom to seek it in all parts Corn was therefore brought to Bordeaux by sea and conveyed thence by river Bordeaux itself seems to have been very dependent at this period upon supplies from England and the corn-growing parts of the interior, and the latter means of supply was often utilised to the full, as in 1401. Scarcity of corn in Gascony that English nobles and officers visiting those parts in the royal service usually purveyed corn in England to supply their needs in Gascony, the Black Prince reserving two manors for this purpose.
The murage in Gloucester collected in the town in 1394 included that on 101 tuns of wine. One branch of waterborne trade in which Gloucester played a significant role was that in corn where town was evidently a centre for the collection of corn from the Vale of Gloucester and from further up river, to be sent for export or to supply Bristol and South Wales. The cattle trade out of Wales presumably continued throughout the period, though a Welsh cowherd who was listed in the roll of traders in 1396. It has sometimes been suggested that many of the visitors to Gloucester in the late Middle Ages came there on pilgrimage. The tradition that the rebuilding of the New Inn in the mid 15th century was to provide lodging for pilgrims was not recorded before the 18th century. The weavers' company and the tanners' company maintained chantry chapels, and ordinances for the tanners made in 1542 illustrate the various roles played by the companies in addition to regulating their trades.
Gloucester's lack of a large merchant class reflected the fact that it was mainly dependent on Bristol for the trade it conducted with the continent. An order made in 1387, commissioning two Gloucester men to check smuggling, stated that goods were shipped overseas directly from the town, but other evidence, though fragmentary, suggests that the town's merchants usually transhipped their goods at Bristol and some joined Bristol merchants in a venture in the Baltic trade in 1389. In 1401 Tewkesbury was one of several towns in Gloucestershire and Worcestershire which Gloucester complained were interfering with those coming to sell corn in its market. The supply of salt to the town, which was being maintained by Droitwich salters in the 1390s and 1481, may also have come by river.
In 1401 Tewkesbury was one of several towns in Gloucestershire and Worcestershire which Gloucester complained were interfering with those coming to sell corn in its market. In 1401 there was a papal exhortation for alms for the repair of the London road at Wotton, and in 1422 the bishop of Worcester offered indulgences for the repair of the Bristol road between Cambridge, in Slimbridge, and Gloucester. Of equal importance to the town was the road coming from South Wales and Hereford by way of the causeway and bridges west of the town, which attracted many bequests in the late Middle Ages. The roads from Painswick and Tewkesbury were also much travelled and, like the three mentioned above, entered the town by official gateways manned by porters. Roadside chapels outside the town are an indication of the amount of travelling. A hermit occupied a chapel at Saintbridge on the Painswick route in the early 16th century and probably collected alms for road repairs. A chapel at Highnam on the South Wales road was used by travellers at the same period, and there may have been another chapel on the Tewkesbury road at Longford, where a wayside cross attracted offerings from travellers.
In 1411 the townspeople joined Bristol in a complaint that they were being forced to hire at extortionate prices trows belonging to men of Bewdley (Worcs.), Shropshire, and Wales for carrying their goods on the upper part of the river; that was disrupting in particular their supplies of firewood, and a group of Gloucester men bringing wood past Bewdley on some kind of raft had been attacked and their cargo lost.
In the late 14th century Gloucester's trade in corn, wine, and other merchandise enriched a small but influential group of merchants. During the 15th century very few Gloucester men can be identified as merchants. One of the few was Philip Monger, who had the major share in overland trade from Southampton in the 1440s, bringing in woad and madder, used as dyestuffs in Gloucester's clothmaking industry, and some wine. It may be that the grain trade on the Severn suffered a decline in the middle years of the century; that situation could lie behind the Crown's response in 1447 to a request for measures to halt the town's decline— permission to build two corn mills at Westgate bridge. Bailiffs of exports gave a number of religious endowments from Banbury to Gloucester and Horsemarling in Moreton Valence parish where ploughlands, shops, and towns were held by exports and merchants and in 1390s, the chantry was founded by bailiffs of one demesne or another.