Of the greatness of Southampton in the Middle Age, however, there can be no doubt.  It was the best exit out of that England into Normandy, the natural port of the capital Winchester, and its whole record is full of glory.  It was in a very real sense the gate of England.  Hither came the great ships from the South and the East, from the ports of Normandy and Anjou, from Bayonne and Venice, with wine and Eastern silks, leather from Cordova, swords and daggers from Toledo, spices from India, and coloured sugars from Egypt.  Here the merchants disembarked to trade in the capital or to attend the great fair of St Giles; hither came the pilgrims, thousands upon thousands, to follow the old road from Winchester to the Shrine of St Thomas at Canterbury; while out of Southampton streamed the chivalry of the Crusades; hence “cheerly to sea” sailed the fleets of Coeur de Lion for Palestine, of Edward III. for France, the army that won at Crecy, the army that won at Agincourt.  All the glory of mediaeval England Southampton has seen pass by.

That the abandonment of Guienne and Aquitaine by the English was a severe blow to Southampton is certain, but still it had the Venice trade, the “Flanders Galleys” laden with the spoil of the East, the wines of the Levant, the “fashions of proud Italy”; and the real decline of Southampton dates from the moment when Venice too was wounded even to death by the discovery of the Cape route to the East and the rise of Portugal.

As it happens we have at the time of her greatest prosperity a description of the town from the hand of Leland.  “There be,” he writes, “in the fair and right strong wall of New Hampton, eight gates.  Over Barr Gate by north is the Domus Civica, and under it the town prison.  There is a great suburb without it, and a great double dyke, well watered on each hand without it.  The East Gate is strong, not so large as Barr Gate, and in its suburb stands St Mary’s Church, to the South Gate joins a Castelet well ordinanced to beat that quarter of the haven.  There is another mean gate a little more south called God’s house gate, of an hospital founded by two merchants joined to it; and not far beyond it is the Water Gate, without which is a quay.  There are two more gates.  The glory of the Castle is in the dungeon, that is both fair and large and strong, both by work and the site of it.  There be five parish churches in the town.  Holy Rood Church standeth in the chief street, which is one of the fairest streets that is in any town in England, and it is well builded for timber building.  There be many fair merchants’ houses, and in the south-east part was a college of Grey Friars.  Here was also an hospital called God’s House, founded by two merchants, appropriated since to Queen’s College, Oxford.”