With a history dating back over 600 years Highbrook is one of the best surviving examples of a hamlet of mediaeval origin. Few places, large or small have so many mediaeval halls still used as dwelling houses.
A hundred years ago, Highbrook was almost inaccessible for the greater part of every winter. All Sussex roads were notoriously bad until relatively recent times, and Hammingden Lane was barely a road. Any vehicle attempting to reach the hamlet after heavy rains was likely to sink into the mud and stay there until extra horses could be brought from the farms to drag it out. Nowadays only thick snow (or the 1987 hurricane) now cut it off from the outside world.
The name of the hamlet was originally Hammingden which is apparently a corruption of Hemele's Denn (swine pasture).
Although there is some debate among archaeologists, it seems most likely that by the beginning of the reign of Henry VIII the hamlet was formed by four medieval halls clustered together on a hill with their associated farms radiating outwards from the centre like a large cartwheel.
After the original halls, several other buildings in and around Highbrook were built up to about 1680, but then there was a building gap of 200 years apart from the Hop Oast which was used for the drying of hops until 1880.
In 1876 the upper floor of the oast was used by a Miss Weguelin as a school. The number of children attending the school quickly increased and the Oast was not large enough. It was then, in 1878, that Miss Weguelin built what is now the Village Hall.
It is noteworthy that this parish, unlike nearby Lindfield, has no Georgian houses.
Much of the information about the Highbrook buildings is taken from an article by Mr. Ian Hannah, published in Volume 83 of the Sussex Archaeological Review, pages 15-34. However, writing in his book "Framed Buildings of the Weald", R.T. Mason disagrees with many of the building dates deduced by Mr Hannah but nonetheless all agree that Highbrook has a fine collection of historical buildings.