The origins of of Stokesley’s traditional fairs can be traced back to the granting of royal charter by Henry III to John FitzRobert in the year 1223-4. The date of the inception of the fair of 1224 is confirmed by the entry in the Online Gazetteer of Market Fairs in England and Wales to 1516. Further, a fair is quoted as being held on the Saturday before Trinity Sunday (around Easter time) in the 6th edition, dated 1770, of Owen’s Book of Fairs.
Stokesley Fair is now held in September each year. Its timing is now determined by the date of Stokesley Agricultural Show. The show was founded in 1859 at a meeting held at The Golden Lion (now Chapters Hotel) High Street, Stokesley and first held on the third Thursday of September in the same year. This remained its traditional timing through to 1967. In 1968 the decision was taken to move the show to a Saturday and it is now held on the Saturday after the third Thursday in September. Stokesley Agricultural Society who organise the show claim that it is the North's largest one day agricultural show.
Crowds of up to 20,000 attend the town’s annual showpiece event and Stokesley Show attracts exhibitors and spectators to the town from around the country, with events running in the main ring throughout the day including show jumping in addition to a wide range of produce tents as well as the animal classes.
Stokesley Fair is held from the Wednesday preceding Stokesley Show to the day of the show. It is open from early evening on Wednesday to Friday inclusive and all day on the Saturday.
The fair takes over most of the open space in the town centre. It is held on the Stokesley Manorial Lands and stretches from West Green and covers the cobbles on both sides of the High Street before extending to full occupy The Plain and then College Square at its eastern extremity.
The fair pays rent to Manorial Lands Trust. The income gained from the fair helps to support the Town Hall Trust and to maintain the manorial lands and the structures built upon them as well as assisting in the promotion of other charitable events for the benefit of the residents of Stokesley.
In 2016 the fair will take place from Wednesday 15 September through to show day on Saturday 17 September.