Brad MerrettComment


Brad MerrettComment

Is Winchelsea the unluckiest town in Britain? It might well be. 

Pronounced ‘winchulsea’, it was once situated a couple of miles south, where the English Channel now splashes and rolls. In the 1200s, giant storms managed to sweep the original town away, meaning ‘new Winchelsea’ was built on a hill above the river Brede, which gave traders and merchants access to the sea. 

The new town was laid out on a strict grid pattern, mimicking 14th-century French towns, a street plan you can still see today. And many of the houses were built with a giant cellar, ready to store the wines that were traded with France, and made the town one of the famous ‘Cinque Ports’. 

The town prospered – until the sea receded, the river narrowed, and the town fell victim to French raids during the 100 Years War. By the 17th century, the town was a shadow of its former self… and so it remained until artists and writers started making the town their home. Ford Madox Ford lived here, as did Joseph Conrad and Henry Irving, the actor. The town gradually stabilised and became the lovely little place it is today. 

On a gorgeous spring day, the views from the hill Winchelsea is situated on are stunning – across the flat marshes to the sea, taking in Camber Castle and Rye perched on the next hill over. The town is limited to a lovely pub (the New Inn) and a great farm shop and butcher. And the walks are fantastic – we did a 6-miler, taking in the Royal Military Canal, Wickham Place (the former home of William Penn, the founder of Pennsylvania and now a B&B) and plenty of sheep.

We hiked over to the next village via Winchelsea’s Strand Gate – still imposing – and stopped for lunch at the Queen’s Head in Icklesham, before turning and walking home across rolling farmland, avoiding the curious sheep and spying on the windmill where Paul McCartney records his music. Centuries of history are spread out before you. It’s a wonderful place to escape London for a day… and as it’s only just over an hour from the capital by train, it’s a journey that’s easily done.


Stranded Winchelsea (hike on to Icklesham if you want a longer walk!)


Winchelsea Farm Kitchen

A lovely little deli, butcher and coffee shop in the heart of the town. 


New Inn
Family-run establishment with delicious food. You can stay here too, if you’d like a night in the town. 

Queen’s Head Inn, Icklesham
Gloriously traditional pub with a great selection of ales and a sturdy menu. Worth the walk from Winchelsea!


Try and coincide your visit with a cellar tour: a chance to visit some of the medieval cellars that are still sited beneath the town’s houses. Find out more here