The town is well-known as an educational centre, and Pocklington School, an old foundation, dating from 1514, is famous as the school which educated William Wilberforce, whose exertions were successful in abolishing slavery throughout the British Empire.

The founder, John Dolman or Dowman, was, it is believed, a native of Pocklington, of the Manor of which his family were lessees; and he obtained a licence to found in the church of Pocklington, a fraternity, or "Guild of the name of Jesus, of the Blessed Virgin Mary, and Saint Nicholas," for a master, two wardens, and a number of brothers and sisters. He obtained permission to grant lands, etc., of the value of 20 marks, to the said Guild, for the maintenance of a learned man to teach Grammar to all scholars resorting to Pocklington for such instruction. When all such religious societies were abolished in 1547, the property originally left to the Guild was, through the exertions of the Founder's family, preserved for the benefit of the school. In 1552 the endowment was transferred to the Master and Fellows of St. John's College, Cam­bridge, the School being re-constituted under the patronage of that College; and the Master and Usher formed a Corporation called the "Corporation of Master and Usher of the Free Grammar School of Pocklington."

The founder devised by will certain lands in Yorkshire and Derbyshire to the Master and Fellows of St. John's College, for the purpose of maintaining in the College five scholars from this School, those of his name and kindred to have the preference.
In 1875, the School was entirely re-organised by the Endowed School Commissioners, who removed the patronage from St. John's College, and appointed a representative Governing Body. This Governing Body was enlarged to 17 members in 1911 when the East Riding County Council assisted the School financially. This assistance came to an end in 1944 when the School was reorganized by the Ministry of Education as a Direct Grant School, and in 1955 the number of Governors was raised to 21 to include representatives of two Yorkshire Universities, the Lord Lieutenant of the East Riding and the Vicar of Pocklington.

In the 1960’s the School was represented on the Headmasters' Conference and the Governing Bodies' Association and provided up to 50 per cent, of Free and Reserved Places to boys sponsored by the East Riding Education Authority, whether Boarders or Day Boys. In 1951 a new Junior School of some 60 boys aged 8 to 12 (over half of whom are Boarders) was opened at Lyndhurst on the Kilnwick Road. In  1960 there were four Boarding Houses in the School with 235 boys out of a total of 405. The School has very fine level playing fields of over 30 acres, with gardens round the Houses, and the buildings include an Assembly Hall built in 1928, Gymnasium, Swimming Bath and Science Block.

The Honours List of the School is lengthy and varied and contains the names of the Most Rev. J. C. H. How, sometime Primus of Scotland, and Lord Moran, personal Physician to Sir Winston Churchill. Among younger Old Boys are two Headmasters of distinguished schools and Richard Annand who was awarded the V.C. for gallantry in Belgium in May, 1940. Many others are found in distinguished positions in the Services, the Law, Commerce and Industry.

From 1890-1910 the School shared with one other Public School most of the University Prizes and Scholarships for the study of Hebrew. Though this is not now taught, Classics form a strong feature of the School's curriculum and in recent years open awards and State Scholar­ships at Oxford and Cambridge have been won in Classics, Modern Subjects, Mathematics and Natural Sciences. The School continues its close association with St. John's College, Cambridge, and has four Dolman Exhibitions tenable there.

The names of those who died for their country in the two World Wars are recorded in the new Memorial Pavilion which was built and presented in 1955 by Old Boys of
the School and looks across the new Memorial Playing Fields to be completed in 1957.

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