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'Uckfield', first recorded in writing as 'Uckefeld' in 1220, is an Anglo-Saxon place name meaning 'open land of a man called Ucca'. It combines an Old English personal name, 'Ucca' with the Old English locational term, 'feld', the latter denoting open country or unencumbered ground (or, from 10th century onwards, arable land). A number of other places in the area also contain the suffix 'feld', which may be an indication of land that contrasts with the surrounding woodlands of the Weald, including in particular Ashdown Forest immediately to the north.

The first mention in historical documents is in the late thirteenth century. Uckfield developed as a stopping-off point on the pilgrimage route between Canterbury, Chichester and Lewes. The settlement began to develop around the bridging point of the river, including the locally-famous Pudding Cake Lane where travellers visited a public house for slices of pudding cake; and the 15th-century Bridge Cottage, the oldest house still standing in Uckfield, now a museum. The town developed in the High Street and in the New Town areas (the latter to the south of the original town centre).

The Eversfield family, who later became prominent in Sussex history, giving their name to the prime waterfront street of St Leonards-on-Sea, first settled in Uckfield from their Surrey beginnings. The family, who later owned the mansion Denne Park in Horsham, which they represented in Parliament, acquired a large fortune through marriage, real estate acquisition and iron foundering. Their climb to wealth and prominence was a heady one: in fifteenth-century Sussex they were described as 'yeomen', but within a generation they were already among the first rank of Sussex gentry.

Parts of Uckfield, owing to its location on the river, have been subject to extensive flooding on a number of occasions, the earliest recorded being in 1852. More recent floods have occurred approximately every nine years: in 1962, 1974, 1989, 1994, 2000 and 2007, although those in 2007 were not as severe as previous floods. Local residents have long been lobbying for flood defences in the town, and recently when the local Somerfield became a Co-op, its car park's walls were rebuilt as flood defences with a ramp to access the car park and a watertight pedestrian gate that can be closed when flooding is imminent. It is hoped that this new wall will act as a reservoir to contain the flood water until it recedes, allowing the water to flow back into the river Uck, which runs alongside the carpark. Due to the positioning of the river within Uckfield, any flooding is within the lowest part of the town centre and industrial estate, and so does not affect residential areas as these are all built on higher ground. The Hempstead Meadows Nature Reserve can be accessed from the car park (now owned by Waitrose, who took over from the Co-op) and shows classic meadows formed on the flood plain.

The West Park Nature Reserve contains a wide variety of habitats; it is located on the western edge of the town.