The earliest reference to an ale house in Castleton was 1577 - when Richard Lea and Richard Altfield had 'Alehowsis'. It was one of these that was probably on the site of Ye Olde Cheshire Cheese Inn. However, the present building was built in 1660 by the Hall family, one of the villages most prominent benefactors.
Their origins remain a mystery but we do know that they have lived in Castleton since medieval times. The building passed down through various members of the family and was at that time a farmstead. In 1748 the building was in possession of a full license and was known as the Wagon and Horses which would remain the name of this inn until 1847 when it became known as the Cheshire Cheese.
 
 During the early 19th century two fairs were established here on the 21st April and on the first Wednesday in October for the sale of cattle, horses, cloth, cheese and agricultural produce. The entire parish of Castleton including the chapel of Edale contained in 1821, 1428 inhabitants.

In February 1849 George Hall became the publican here. The Wagon and Horses was one of five inns that existed here at this period, the others being the Bulls Head, the Nags Head, the Butchers Arms and the George and Dragon kept by another member of the Hall family. By 1845 the farm land around the inn had been reduced to 14 acres.

Castleton's famous Garland ceremony (Oak Apple Day) takes place on 29th May each year in commemoration of the restoration of Charles II to the throne. The ceremonial parade starts from Ye Olde Cheshire Cheese.