Pipewell Gate gave access to the ferry and later to the road which led from Winchelsea to Rye.

Its alternative name is Ferry Gate. It is newer than the others. Destroyed in the French attack in 1380, it was rebuilt in 1404 by John Helde the Mayor. The remains of his shield can be seen on the ferry side of the gate.

The road plunges down hill beneath a steep cliff and it was here that King Edward I had a miraculous escape. He was at Winchelsea to view the fleet, loading for his Flanders campaign, and approached the top of the cliff, which was crowned only by a low earth wall. His horse shied at a nearby windmill, jumped the wall then, with its rider, disappeared down the precipice. Crowding horror-struck to the edge, the townsfolk were in time to see the horse land a full thirty feet below on the road, where it slid twelve paces, stumbling and staggering before the king, still in his saddle

“turned him round with the rein and rode him straight up to the gate. When he passed through the gate the people standing round were filled with great joy and wonder in contemplation of the divine miracle by which the King was preserved.”

Conservation work was carried out by Winchelsea Corporation in 2016 with funding from The Friends of the Ancient Monuments (FOAM) and generous contributions from members of the local community.