The name "Chailey" allegedly derives from the Saxon word "chag", which referred to the gorse and broom, which grew in the area. It has changed numerous times over the years, probably owing to mis-pronunciation and the poor literacy of those who recorded the name. Between 1087 and 1100, it was known as "Chagleigh" and pre-1609, Chagley. It was therefore only a small further step to become the present "Chailey".
Geographically, Chailey lies either side of the A275, and is reputedly the very centre of the county of Sussex. It is said that an ancient yew tree, beside the windmill on North Common, marks the exact centre. Other claims include being the largest parish in Sussex and historically one of the poorest.
There are numerous references to parishioners being given relief in the County Poor Law records between 1601 and 1835. The original Chailey Workhouse was situated on North Common, but in 1833, after the amalgamation of several other village Poor Houses, it moved to the "Pouchlands" site. Workhouses were abolished in 1933 and the premises then became a Hospital. The original North Common site was acquired by Brighton Borough to be used as a Technical School, but eventually was taken over to become the now famous "Chailey Heritage". It is here that children with special needs, many of whom are resident, receive education and treatment to enhance the quality of their lives. Recently Chailey Enterprise Centre has been established, which uses computer technology to produce a wide variety of consumer goods, the sale of which supports projects within the Heritage. The Enterprise Centre also employs past pupils of the school.
In the 'Last Will and Testament' of Thomas Thompsett, published on 8th February 1769, the sum of £40 was left to the then Rector of St Peter's, the interest on which was to be used to send four poor boys to school. In 1770, a cottage was purchased with the principal sum and by 1819 with the £7 a year rent it was possible to send not four but six boys to school. The school in question was at that time on the village green, but in 1852, it moved to the site of the present Primary School. The Thompsett Charity is still in existence and regularly finances educational trips for young people from the village. As well as the school, there were, surrounding the village green, a general store, butchers shop, tailors, Post Office, blacksmiths, a cobblers and a builders yard. These businesses no longer exist, but we still have a thriving shop and Post Office on the A275 just south of the Horns Lodge Public House.
Farming is and always has been the mainstay as far as work is concerned in Chailey. The village does, however, stand on the clay belt and for the past 250 years has been noted for its pottery, terra-cotta flowerpots, tiles and bricks. The original works were founded by the 'Norman' family, but now are owned by 'Ibstock'. In years gone by, as in other parts of Sussex, iron was smelted here, and the resultant slag and cinders were used to surface the roads. Evidence of this can be found in local place names, such as 'Cinder Hill'. To the north of the village in 1898, Mr Albert Turner established sawmills, on land owned by Lord Sheffield. It was originally powered by water from the River Ouse, but this was found to be inefficient and the operation eventually converted to steam power. The company changed hands several times and in later years was owned by the Finnish company Woodpax Ltd. In the same area was a dairy known as the 'Sheffield Park Creamery'. This undertaking still survives and continues to expand, now being owned by 'Express Dairies'.
During the 1914 to 1918 conflict, no less than 238 men from the village served in the armed forces, of whom 45 were never to return. They are commemorated on the Memorial, which stands on the village green. In the Second World War, Chailey residents once again answered the call to arms, with 172 men and 20 women serving in the various Armed Services. The loss of life, though significant, was not as great as in the earlier conflict and is similarly remembered on our war memorial. Prior to the D-Day landings in Normandy, many hundreds of American and Canadian troops were camped in the wooded area which surrounds the present brickworks. If you look hard enough, you can still find evidence of their passing. Chailey Commons have also been used repeatedly for military training purposes over the years, as documented here. As a result, some evidence of the activity may still be detected, as described here. Chailey also had its own airfield, largely manned by Polish Airmen, who provided much needed air cover for the ground troops engaged in 'Operation Overlord'. A memorial to these brave men now stands adjacent to the new Plough Inn, the original pub having been demolished to facilitate aircraft operations.