What it cannot convey is how strange and contested the ground beneath all of that had been for the previous two centuries. By 1415, the town had been burned by neighbouring Irish forces, and the Crown was moved to grant its people the right to collect tolls for forty years, on the condition that they use the money to wall their own streets and build their own defences, with accounts rendered not to the Treasury but to the Earl of Ormond. This was not a prosperous market town with an orderly past; it was a frontier settlement, repeatedly threatened, repeatedly rebuilt, and shaped at every stage by the anxious politics of the Anglo-Norman march.

The place had significance long before any of that. Bealach Ghabhrain, the pass that gave Gowran its name, was a key route between Ossory and Leinster, and the chief rulers of Ossory kept a royal residence here before the Anglo-Normans arrived. In 1172, following Strongbow's acquisition of the Kingdom of Leinster, Gowran passed to Theobald fitz Walter, Chief Butler of Ireland, who likely raised a motte and bailey castle, the form of fortification favoured by Norman lords, consisting of an earthen mound topped by a wooden tower beside an enclosed courtyard. Before his death in 1206, fitz Walter had already granted a charter of incorporation to his free burgesses. By the mid-thirteenth century, the Knights Templars held rights over the rectory, and around 1307 to 1310, oak timber from their woods at Athkilton was being used to repair houses in the town. The parish church became a burial place for the Butler family: Edmund Butler, Earl of Carrick, who died in London returning from a pilgrimage to Santiago de Compostela, was interred there in 1321, and his son James, the 1st Earl of Ormond, followed him in 1337. A further castle, built around 1385 by James Butler, the 3rd Earl of Ormond, no longer survives, though its site was still being marked on maps as late as 1900, approximately seventy-five metres northeast of the later Gowran Castle built by Viscount Clifden in 1816.

The town's street plan, partially captured in a 1710/11 map, reveals a settlement of some complexity. A mid-sixteenth-century rental account names seven gates in all, including the Magdalen Gate to the east, the West Gate, a Castle Gate, and one called Tibirdowanis barr, probably derived from the Irish Tobar an Domhnaigh, meaning Sunday's Well. By 1501, the townspeople were petitioning the Earl of Ormond to be relieved of coyne and livery, the obligation to billet and feed troops at their own expense, a burden that had been outlawed within the Pale since 1488 but persisted in the march lands. The cobbled surface of what may have been Haggerd Street, a lane running outside the southern town wall, was uncovered in excavations as recently as 2006, a quiet reminder that a great deal of the town's medieval fabric is still underfoot.