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English town nicknamed the ‘medieval Manhattan’ with grid-like roads and secret beach

THE East Sussex town of Winchelsea has a beautiful beach and a very unique road layout.

A little-known fact about Winchelsea is that it was built in a grid formation, and for the very sad reason that Old Winchelsea fell into the sea.

Winchelsea town sign and Court Hall.
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Winchelsea was built in the late 13th century[/caption]

Church of St. Thomas the Martyr ruins and graveyard.
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St Thomas the Martyr Church was built as part of the new town[/caption]

Starting with a little bit of history, the original Old Winchelsea dates back to the 9th century and was built on a shingle beach.

Not only was it used as a port for trade, the town was also a line of defence and housed one of the biggest naval ports in the UK.

In its heyday, Old Winchelsea was said to have over 700 houses, two churches, and 50 inns and taverns.

Although there’s no exact figure, it implies thousands of people once lived there.

But life in Old Winchelsea literally came crumbling down when England was hit by violent storms in 1287, and the town actually fell into the sea.

After the flood, the king at the time, Edward I, wanted a new Winchelsea, so one was built a few miles inland on the Hill of Iham.

When the new town was designed, it was uniquely done with a grid-like pattern which is where it got its nickname, a ‘Medieval Manhattan’.

The roads and streets were created to form an obvious grid formation all set in 39 blocks which was used to help with orientation and locals finding their way around.

Underneath the town, you’ll find a maze of underground cellars which were part of the new town plan as well.

Their creation was because Winchelsea was a big player in the wine trade – in the 14th century, the equivalent of four million bottles a year passed through the town.


Winchelsea Beach at dawn with the moon in the sky and old wooden posts in the shallow water.
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A flood in 1287 completely destroyed Old Winchelsea[/caption]

In the town today, there are 140 listed buildings and part of the new town build at the end of the 13th century still stand.

The parish church, St Thomas the Martyr, was built as part of Edward I’s plan for the new town.

There are also medieval stone-vaulted wine cellars that remain, and New Gate, which was once the entry way into the town, is now a ruin across the road.

Only 600 people live in Winchelsea now, it’s a charming town with locally run pubs, tearooms and vineyards.

Grade II listed building and town well in Winchelsea, East Sussex.
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Winchelsea has over 100 listed buildings in the town with some dating back to the 13th century[/caption]

White cottage with pink roses and lavender.
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The small town today is home to just 600 residents[/caption]

There’s also a family run vineyard called, Charles Palmer Vineyards, with people saying there’s “no need to go to France” with their tours and tastings.

The vineyard, across 120 acres, makes Pinot Noir and Chardonnay.

The shingle beach is well-sought out too, with one visitor saying it’s the “country’s best-kept secret”; another added it’s “best for long walks, even in winter”.

On the beach you’ll also see the old wooden sea defences at Winchelsea beach.

The New Inn pub in Winchelsea has “old world charm” and was recommended by Restaurant Guru in 2023.

Stone archway ruins with trees growing through.
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This New Gate ruin used to be the entry way to Winchelsea[/caption]

They offer the classic pub grub and even have four rooms to stay in from £130 per night with some having a view over the village and medieval church.

On the high street there’s the Winchelsea Farm Kitchen which is a cafe, butcher, wine cellar and antiques shop – you can have high tea for £11.95.

Just up the road is the village of Rye, which last year was named the best half term day trip.

Called one of England’s quaintest towns, the main Mermaid Street feels like stepping back in time.

Originally a fishing port, it was a famous pirate port in the 13th century – now it is a popular staycation spot with tiny hotels, restaurants and cafes to explore.

Winchelsea Beach at dawn with the moon in the sky and old wooden posts reflected in the water.
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You can see the old groynes of Winchlsea that are still on the shingle beach[/caption]

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