Kirkham was founded by Walter L'Espec the same man who erected the grand Abbey of Rievaulx. Unfortunately, it did not get off to a good start, for its patron's greater interest in the Cistercian way of life led to many of Kirkham's canons leaving for that order not long after its establishment. They were temporarily installed at Linton and given permission to take all Kirkham's fixtures and fittings with them. Even the stained glass from the windows!

The priory survived, however, and was must patronised by the De Roos Lords of Helmsley in the 13th and 14th centuries. Many of them were buried in the, now ruined, priory church and records reveal the tomb remains on the southern side of the presbytery to be those of Lords William (1343) and Robert (1285).

The monastery is best known for its beautiful gatehouse: an attractive 13th century structure, the north face of which is enriched by De Roos heraldic devices and religious sculptures. Here we have St. George & the Dragon, David & Goliath, a seated Christ and a number of the apostles.