Some archaeologists date the town to the Roman occupation, when it may have been a military fortification. Discovery of a few Roman artefacts support this. Gighesbore is recorded in the Domesday Book. The ruined Gisborough Priory dates from the 12th century.
Guisborough market, held every Thursday and Saturday with a few stalls on Tuesday, has long been a focal point for the surrounding area. Originally selling cattle and other livestock, the market developed into a general market for fruit and vegetables, clothing and flowers. It is open from early morning to late afternoon on the recently restored cobbles of Westgate, the principal shopping street.