Discover Winchelsea: town gates, history and walking routes

Discover Winchelsea from different perspectives: the layout of New Winchelsea reflects the town’s founding, while its gates, church and moat offer tangible traces of history. There are also walking routes, a viewpoint and tours held at certain times of year. If you’re looking for a hotel for a trip to Winchelsea, these themes can help you choose what to focus on during your stay.

The town’s founding and medieval defences

Winchelsea New Town was founded on Iham Hill by Edward I in 1288. Its streets were laid out to intersect more or less at right angles. The town’s history is therefore reflected not only in individual buildings but also in the layout of its streets.

Strand Gate is an original town gate from the late 13th century that provided access to Winchelsea Harbour. New Gate was also built in the 13th century. The town moat served a different purpose: it was an effective part of the defences. These historic features represent different aspects of the town—access to the harbour and defence.

St Thomas and views across Romney Marsh

St Thomas Church is known for its 20th-century stained-glass windows by Douglas Strachan and its medieval Alard tombs. The two features date from different periods: the windows are from the 20th century, while the tombs are medieval. Together, they offer a tangible connection to different eras in the town’s history.

The Lookout offers a different perspective: from this viewpoint, you can see across the whole of Romney Marsh. Here, the focus is not on a single building but on the panorama across the Marsh.

Since 1975, the National Trust has protected Winchelsea’s character by acquiring Wickham Manor Farm; the land acquired includes a ring of land on three sides of the town. Winchelsea is also now a Conservation Area. This information complements the history of individual gates and buildings with a broader view of the character of the town and its surroundings.

Planning walks and tours

A network of footpaths runs through Winchelsea. The path along the Royal Military Canal also runs along the eastern edge: heading south, it leads to the sea at Pett; heading north, it leads to Rye. This lets you distinguish the routes in town from the Canal path and take both directions into account when planning.

The 2026 visitor guide lists historic walking tours of Winchelsea from May to September. They include Court Hall and the museum. Check the specific dates before you travel. Tours of the medieval cellars run from April to October, usually on Saturday mornings; you should check the dates for these in advance too. The tours cover different subjects: the historic walking tours include Court Hall and the museum, while the other tour focuses on the medieval cellars.

The station’s location is another useful landmark if you’re arriving on foot: Winchelsea station is a 15-minute walk from the town centre. If you arrive by train, you can allow for this walking time on the journey from the station to the centre. Together with the seasonal tours and the different routes, this gives you a practical basis for planning your visit around your travel dates.

Discover more destinations: Brightling, Robertsbridge, Mountfield, Heathfield, Catsfield, Polegate, Winchelsea Beach, Peasmarsh.

For an overview of the wider area: East Sussex.