Mrs Ann Pritchard Sergison, a member of a Cuckfield family, died in 1848 aged eighty-five. She was known as 'wicked Dame Sergison' on account of her foul temper. After her death, ghost stories began to circulate about her. There are reports of her haunting the avenue to Cuckfield Park and also in the corridors and on the main stairway. Apparently she objected to her daughter's marriage and was seen as a ghost at the wedding reception in 1890. People said she was too wicked to rest, and her spirit swung on the oak gates at the entrance to Cuckfield Park. After some time, three local churchmen were supposed to have held a service of exorcism in Cuckfield church at midnight. The story continued that the ghost was then drowned in the font, and the manifestations came to an end. An alternative theory for the cessation of her hauntings were that the grandson replaced the old oak gates with new spiked ones mde or iron. Dame Sergison was not the only Cuckfield ghost by any means.

There was also Geranium Jane who was said to haunt the local pub, The King's Head. Geranium Jane was a young girl in the 19th century who was having an affair with the licensee. After a lovers' quarrel when he found out she was pregnant, he killed her by dropping a flowerpot planted with geraniums on her head as she passed beneath a window. She was buried in the churchyard but returned as a ghost always accompanied by a strong smell of geraniums. Dogs were said to growl and raise their hackles when she appeared. She stayed away when geraniums were banished from the inn.

At Ockenden Manor Hotel (formerly Ockenden House) a phantom grey lady has been seen in one of the corridors and also in the Elizabethan bedroom. It is believed to be that of a chambermaid who was killed when one of the tunnels leading to the Kings Head Inn in South Street collapsed in the 19th century. She is known to have used that route to meet her lover, but one evening, after the manor "shook as if affected by an earthquake" her crushed and mangled body was discovered in the rubble beneath the building.