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Winchelsea was another of the Cinque Ports, which dramatically declined from its heyday as the Black Death and French raids extracted a heavy toll. Today it has receded to a village-like tranquillity. Originally the town was further down the slope, but was ruined by an enormous storm in 1287. Although most of the buildings are post medieval, you can see in one of two places some vaulted cellars beneath them that were built for storing wine in medieval times.
One of the two main gateways, the Strand Gate looks down to the Royal Military Canal, built during the Napoleonic wars. The Church of St Thomas fills one square of the grid plan and partly stands in ruins though there are some impressive canopied tombs in the church itself. Overlooking it, the stone-built Winchester Court Hall Museum houses local history displays, including a model of the medieval town. Virtually adjacent, the New Inn is a thoroughly traditional pub that makes a good place for lunch.
South of town the so-called New Gate stands rather forlornly in a field by itself, a most atmospheric ruin which you can see by following the clearly waymarked 1066 Country Walk.
Follow the road at the east end of the village leading to Winchelsea Beach and the coast. From here the road follows close to the coast before diverting inland to Fairlight. You can stride out to some of the finest stretch of undeveloped cliffs in the South-East from the car park here, towards Fairlight Glen and along the coast to Hastings.
To continue the tour, turn left on the A21 into the hilly seaside town of Hastings.