Winchelsea is an historic town in an Area of Outstanding Natural Beauty on the East Sussex coast. With surrounding countryside protected by the National Trust, there are spectacular views along the Brede Valley and across Rye Bay to Dungeness. Winchelsea is one of the best preserved medieval planned towns in the country, with streets laid out on a rectangular grid pattern. Founded in the late thirteenth century as a port by King Edward I, it replaced Old Winchelsea which was swept away by ferocious storms and the rising sea. 

Underneath New Winchelsea lies a large network of medieval cellars, bearing testimony to the town’s importance to the wine trade in the 14th century, when the equivalent of four million bottles a year passed this way.

With a combination of royal patronage and its membership of the Confederation of Cinque Ports, the new town of Winchelsea thrived and during the 14th century became one of the primary ports of the realm, but by the end of the 15th century the coastline had shifted, the river had silted up and the final merchants had left.

With a once thriving population of around 5000 people, the Town today has around 500 inhabitants, possibly classed as the smallest Town in England, and a hidden gem.

In the 19th century picturesque Winchelsea became a favourite haunt of artists and writers. Turner and Millais painted here; Thackeray, Coventry Patmore and Conrad wrote here; Ford Madox Ford lived here as did the great Victorian actress Ellen Terry.

Though no longer a local authority, the Corporation of Winchelsea is a registered charity and maintains the historical traditions of the town and is also responsible for the upkeep of its ancient monuments including the gates, Court Hall and Museum.


Winchelsea Court Hall Museum: The Court Hall Museum tells the story of the town’s history, from its medieval origins to the present day. Staffed by knowledgeable volunteers, the Museum is regularly open from Spring to Autumn.

St Thomas the Martyr Church: One of the finest church buildings in Sussex despite the ravages of the Hundred Years’ War which left it severely damaged with only the chancel remaining. Inside are six splendid medieval canopied tombs. The remarkable stained glass windows were designed by Douglas Strachan and installed between 1929 and 1933. Comedian Spike Milligan lived in nearby Udimore and is buried in the churchyard

The Winchelsea Cellars: The stone-vaulted medieval cellars are a key part of the town’s history. Only Southampton has similar numbers of the same quality. From April to October, knowledgeable local guides run fascinating tours. Details of how to book can be found online here

The Town Gates: Winchelsea has three surviving medieval gates. Traffic still comes up to the town through the Strand Gate. The picturesque New Gate is now well outside the settlement, a testament to how extensive the town once was. The 1066 Country Walk also passes through, connecting Battle and Rye.


For further information, details of events, things to see and do, or download the free ‘Discover Winchelsea’ visitor guide and map please visit: winchelsea.com