As the rain washes through New York City this week, we can’t help make the comparison to the wet counterpart across the pond in England.
In fact this week, we discovered one of the nation’s biggest hidden gems—a charming English town that’s basically a medieval version of Manhattan—meet Winchelsea, the “English Manhattan.”
Nestled in the rolling hills of East Sussex, this hidden gem captured our hearts thanks to its unique street grid—not glass skyscrapers, but a centuries-old urban design that feels surprisingly modern.
Let’s dive into what makes this jaw-dropping “English Manhattan” so special, shall we?
Why is Winchelsea called the “English Manhattan”?
Winchelsea earns its nickname as the “English Manhattan” thanks to its remarkably planned grid street layout—a true rarity in medieval England.
Unlike other Manhattan-style cities that compare due to skyscrapers, this town resembles the borough’s highly organized grid of parallel and intersecting streets, much like the iconic street plan of Manhattan.
Winchelsea’s “blocks” are lined with historic cottages, ancient cellars, and remnants of its storied past. The town’s grid layout was planned way back in 1288 after the original settlement was destroyed by flooding a year earlier, and King Edward I ordered the construction of a new settlement on higher ground.
Low and behold, it became one of the earliest examples of urban planning in England, and was one of the most ambitious designs at the time.
The town featured five main streets running north-south, crossed by several east-west streets, creating a series of blocks or “quarters.” These were even numbered rather than named—a strikingly modern touch that echoes the numbered streets of Manhattan today.
This grid was likely influenced by the “bastide” towns of southwest France, which King Edward I knew from his holdings in Gascony.
With orderly streets, dedicated markets, and prominent churches at the forefront of the design, every detail was done with purpose—like a church in the center as a community symbol for example.
The significance of Winchelsea’s grid
What’s fascinating is the grid streets were not just for aesthetics.
It reflected the town’s importance as a major port and member of the Cinque Ports, a powerful medieval confederation that provided ships and men for the Crown in exchange for special privileges.
The layout made Winchelsea easy to defend, navigate, and administer, with the Church of St. Thomas at its center and three impressive town gates still standing today.
The grid also facilitated commerce, as the town’s Monday market was purposefully placed within a square defined by the intersecting streets.
Today the grid remains visible and walkable, offering visitors the chance to walk down one of the greatest medieval port towns in the country.
Winchelsea today: timeless charm & things to do
Winchelsea may be small, but it’s packed with medieval history and charm! We highly recommend taking a day trip here if visiting London, since it’s only 2 hours away from the city!
We’ve put together your Winchester bucket list together so you don’t have to, check it out:
- Ancient Cellars: Descend into the town’s medieval wine cellars via guided tours. There’s over 50 different ones that live underground and date back to the 1300s. View here
- St. Thomas the Martyr Church: Marvel at the beautiful stained glass windows and the tomb of Spike Milligan, the legendary comedian. View here
- Town Gates: Snap photos at the iconic Strand Gate and New Gate, remnants of the town’s original defenses.
- Secret Gardens: Wander through the National Trust’s Winchelsea gardens, bursting with blooms in summer. View here
- Winchelsea Museum: Dive into the town’s fascinating history, from shipwrecks to smuggling tales through maps, models, pictures, local pottery and more items. View here
- Walk the Grid: Stroll the perfectly straight streets and imagine you’re in a medieval Manhattan-without the traffic!