The location of a Roman fort at Watercrook, the pre-10th century church site at Kendal (suggested by the place-name element Kirkby, ‘church settlement’) and the pre-Conquest estate centre just north of the town at ‘Strickland’ (recorded in Domesday Book) all suggest that the vicinity of the later town had become a focal point for the surrounding area long before the borough was founded. On the establishment of the barony of Kendal in the 12th century, the first baron, Gilbert fitz Roger fitz Reinfred, acquired a market charter for Kendal in 1189; it is likely that this, and the borough charter granted to the inhabitants by Gilbert’s son, William de Lancaster III, in the first half of the 13th century, confirmed an existing trading centre. The borough, focused on a market place at the junction of the route from the north over Stramongate Bridge with the main route up the Kent valley, grew up north of the church and close to the seats of baronial power, the Norman motte and bailey castle (now Castle Howe) and its 13th-century successor, Kendal Castle, to the east of the river.
The medieval town would have served as the market, religious and administrative centre for the whole of the barony, though the influence of the barons of Kendal would have been weakened by the partition of the barony between heiresses after 1246. References to a fulling mill in 1274 and a dyeworks in 1310 suggest that the woollen textile industry was well established by 1300.