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The History Of Winchelsea

A Town Planned: the roads to Winchelsea

There were two main overland routes into Winchelsea. Both primarily provided access to the main market square. The first route was from Pett and Fairlight, and entered the town through the New Gate in the south of the town. The second and more important route was from Icklesham and thence Hastings, and followed what is now the A259 entering Winchelsea by a gate on the western side of the town which is now lost (known as the Pewes Gate). This gate opened into Sixth Street (also lost) which ran to the south side of the market square. However, it appears that this route, being quite steep, was not popular and those coming into the town actually turned north (left) at the Pewes Gate and took Fifth Street (which was made less steep by means of a cutting) to the north side of the market square. The present day Hogtrough Lane is a remnant of Fifth Street. By the early 15th century, the preferred route had changed again, this time to follow the current road into Winchelsea from Icklesham: leaving the present day A259 at the top of Sandrock Hill (historically known as Gallows Hill) to follow what today is called Monks Walk. In the 15th century, Monks Walk as far as St Johns Hospital wall was part of Seventh Street.

The other two main routes into Winchelsea led from the port area and from the ferry which crossed the River Brede to Udimore (and thence to Rye). The road from the port (known historically as Strand Causeway or Watchbell Causeway) climbed the eastern side of Iham Hill and entered the town by the Strand Gate in the north east, then continued into the town as Third Street (now the High Street). The road from the ferry (known historically as Pipewell Causeway) entered the town by the Ferry or Pipewell Gate in the north, coming up what is now Ferry Hill. The ferry itself was at the end of a causeway projecting out into the Brede and would have been where there is now a bridge over the river. The Ferry House survives. The ferry was replaced by a bridge only in 1657, by which time, the Brede had ceased to be navigable.

Pre-dating the new town was a road that skirted the western and northern base of Iham Hill. It ran from the extreme southerly tip of the hill (where the New Gate was subsequently sited), climbed up the western side of the hill to pass through the settlement of Iham before descending to the base of the hill once again. The road then ran between the northern foot of the hill and the River Brede. The route is still discernible along the northwestern side of the hill and part of it is a public footpath (called Pook Lane). Sections of the original paving are exposed in places.

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