Before the modern local government system came into operation in the late 19th century it was described as being "in the hundred of Buttinghill, in the rape of Lewes".

The origin of the name, Cuckfield (earlier spelled Kukefeld, Cucufeld, and Cucufelda), is debated but it is generally associated with the cuckoo which is the village emblem.

The village grew as a market town; and an important coaching stop between London and Brighton, since it lay on the turnpike.

In 1820, 50 coaches a day were passing through; but when the railway to Brighton was to be constructed in the 1840s, local landowners objected to its projected route: it was therefore built through neighbouring Haywards Heath instead.

The lych gates are listed buildings and several of the stained glass windows as well as the pulpit and the ceiling's painting were designed by Charles Eamer Kempe (1837–1907).

Other attractions include the Elizabethan stately home, Cuckfield Park, to the west of the village.

Another Elizabethan house, Ockenden Manor, is a hotel and restaurant which has had one star from the Michelin Guide in 2001 and again 2004–2016.