Prehistoric activity in this area is attested by the discovery of Neolithic and Bronze – age axes in fields at Brandesburton in the 19^th and 20^th century. Iron Age and Anglican pottery has also been found in areas to the east of the Village.

The settlement is recorded in the Domesday Book in AD 1086 as Bortun, referring to a ‘fortified farmstead belonging to Brandr’. This was part of the lands of the Archbishop of York and Drogo de Brevere, held by Sveinn, Ulfr, Ketilfrothr, and Earnwine. A cleric, villagers and a soldier are also mentioned.

A number of fields surrounding the village preserve evidence for ridge and furrow, a distinctive characteristic of medieval farming activity. The character of the medieval settlement itself appears to have been of an irregular plan with several nucleations.

Remains of this medieval settlement are sparse, although the Church of St Mary preserves 12^th-14^th century elements in the chancel, nave aisles, tower and porch.

On Cross Hill, at the centre of the small village green stands the medieval market cross which is designated as a scheduled ancient monument. This comprises a very weathered, octagonal shaft about ten feet high on square, stepped plinth. In 1840, Poulson recorded that there appeared to be two standing figures, back-to-back surmounting the cross, their hands joined in an attitude of prayer.

It is alleged that stocks once stood near to the market cross, although there is no trace of these surviving.