The ancient city of Winchelsea

Explore a 13th-century Cinque Port now more grass than house and which the sea has long deserted.




2 miles (3.2kms)

108ft (33m)
1hr 15min

About the walk

For a while, from the late 13th century until the mid-14th, Winchelsea thrived as an important port, specialising in the wine trade with English Gascony. Technically ‘New Winchelsea’, the town was planted on higher ground after the original Cinque Port of ‘old’ Winchelsea had been washed away in the 1250s.

The new town was laid out by the then Warden of the Cinque Ports at King Edward I’s request. It was designed by an experienced builder of French bastides (fortified towns), Itier Bochard. Bochard set out a grid of generous streets surrounding larger than normal plots for those times, and also incorporated the old Anglo-Saxon village of Iham. Following Edward’s promises of seven years occupation of a plot rent-free, the town began to fill up rapidly.

A failed port

Although initially successful, Winchelsea never filled its 39 ‘insulae’ or groups of plots within its street grid. It is difficult nowadays to realise how dangerous the English Channel was in the Middle Ages, with constant raids on the towns of the south coast. Winchelsea suffered severely from French and Spanish raids during the Hundred Years War, with much of the nave of the very large Church of St Thomas destroyed and never rebuilt. The Black Death devastated the town, and the town walls were never completed. By the late 14th century, rents were being drastically reduced for the 387 tenements or houses in the town.

Astonishingly, the town almost disappeared, with only about 60 houses occupied by 1575. The harbour had already silted up, the sea was in retreat. The present town, or rather village, has dwellings only in 12 of the 39 ‘insulae’ within the northern end of the town boundaries, and the bulk of those are relatively modern. Fragments of the old town survive – these include a large number of stone cellars used by the merchants for storing imported wine, the magnificent early 14th-century choir of St Thomas’ Church, the gable of one of the three medieval hospitals, three town gates, the remains of a Franciscan church and the old courthouse in the High Street. Now there is more pasture, grass and woodland within the old boundaries than buildings. It is a great surprise to find the original south gate, New Gate, some 875yds (800m) beyond the last house in present day Winchelsea and realise the town once stretched that far south. As traveller Celia Fiennes wrote in 1697, ‘grass grows now where Winchelsea was, as was once said of Troy’.

Walk directions

From the entrance to the churchyard opposite the New Inn, go past the war memorial and diagonally across past the entrance to the church, to leave by the opposite corner of the churchyard then along Rookery Lane (left of White Cottage). At the end turn left and pass a thatched stable with views to Dungeness.

At the crossroads look right to 14th-century Strand Gate, but continue ahead along Barrack Square, which soon bends left. At the end turn left into Mill Road and at the next crossroads turn right into Castle Street. At the end go left into North Street to descend towards Pipewell Gate.

Pass through the stone arch of Pipewell Gate, which was rebuilt around 1400 after the Spanish raid of 1380, descend Ferry Hill, now the A259, and at the hairpin bend go left over a stile beside a gate onto the 1066 Country Walk route.

Now in the countryside, continue ahead past the Southern Water Treatment Works, over a footbridge and through a gate, then over two more footbridges and through a gate into a field. Go left alongside the old medieval town ditch and ramparts and at the footpath sign continue uphill, still beside the ditch with a view of Icklesham ahead. Through a gate the path continues uphill, the valley increasingly far below to your right.

Go left through a gate onto Beacon Hill, another fine viewpoint and the site of a windmill blown down in the 1987 storms and now with a Millennium Beacon. From the hill, head along the grassy track towards the nearest house to a gate and back towards the town, the path now Mill Lane. At the crossroads turn right along the pavement on the far side, passing the remains of Blackfriars Barn, actually the remains of a medieval house.

Go right through a kissing gate by a lamppost to cross the cricket field to a gate, continuing ahead to a footpath sign. Here go left now back alongside the town ramparts and ditch to descend towards the A259 amid sheep-cropped pastures. Go through a gate to continue ahead along a track. Reaching the main road by The Lodge hotel, turn left to walk along the grassy verge to climb back onto Winchelsea's ridge.

At the hairpin, carefully cross the main road towards the narrow arch sign, passing on your right a stone gable wall, the remains of medieval St John's Hospital. At the junction turn left to follow the road alongside a stone wall, now in Monk's Walk, back to the church and the end of the walk.

Additional information

Village pavements, some road verges and field paths, 1 stile

Ridge top town/village with wide views and sheep pasture

On lead in town and in sheep pasture to west of the town

OS Explorer 124 Hastings & Bexhill or 125 Romney Marsh, Rye & Winchelsea

Roadside parking in High Street near St Thomas Church at Winchelsea

In Monks Walk, Winchelsea

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