Whilst there is no mention of the village of Fairwarp (Fayre Wharp) until 1519 there are significant Roman connections in the area.

At Duddleswell there is a preserved section of a road that ran across the Ashdown Forest and onto London from Lewes. This is part of Ermine Street. The road was built around 100 AD and made of slag and cinders, probably from the iron industry of the area.

There is evidence that the Romans produced iron as a bloomery (early furnace) has been found in the Fairwarp area. The name Oldlands is suggested comes from “old ironworking lands”. Here a number of Roman Coins have been found.

Local heresay claims that there was a Roman posting station at Duddleswell. The origin of the name Duddleswell comes from a chapel, St Dudeneys – Dudeney’s well.