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Wonderful Winchelsea in East Sussex

You cannot visit the very east of East Sussex without being instinctively drawn to Winchelsea. It feels like a quiet if beautiful village perched on top of a hill. But it’s much more than that! And despite its diminutive size, it is in fact a town.

A look back

The original Winchelsea (Old Winchelsea) was largely obliterated in a great storm in 1287. As a result, New Winchelsea was built in its current position not far from Rye from about 1288. It’s laid out and designed in a sort of grid style and underneath it, there is a network of rather intriguing cellars, some with vaulted roofs of Caen stone.

Winchelsea was one of the Cinque Ports – originally five ports (Sandwich, Dover, Hythe, New Romney, and Hastings) to which were later added Winchelsea and Rye. Cinque Ports were a confederation of ports that enjoyed protection and privileges from the Crown in return for providing coastal defence, ships, and even sailors.

Certainly, by the 14th century, Winchelsea must have been a very different place to what it is now, bustling with life, a centre of shipbuilding, trade, fishing, and wine.  And perhaps the odd pirate as well!

Winchelsea Sussex

A stroll around

There are three surviving medieval gates, two of which herald your arrival. The Strand Gate was built in 1300. Originally it would have been considerably higher and rendered white which must have made for quite an entrance for those arriving from the sea. The Pipewell Gate was the ferry entrance and gave access to the road to Rye. Having been destroyed by the French it was rebuilt in 1404.  There’s a legend attached to this gate that during a visit in 1297, King Edward I’s horse shied and disappeared over the edge with the King on board. The horse is supposed to have landed 30 ft below with the King still in the saddle! A little way from the town itself is the 13th century New Gate through which the French are supposed to have attacked in 1380.


In the heart of the town is St Thomas’ Church which has its own wow factor and parts of this date back to the 13th century.  Today, there’s a certain tranquillity about the church and its graveyard but even though it’s not the only church in the town, it still feels like it dominates. It has a notable stained glass window and the well-known Medieval tomb of Admiral Sir Gervase Alard (1270-1340), an English knight and naval commander who was appointed Admiral of the Cinque Ports Fleet and Admiral of the Western Fleet of the English Navy and who served under Kings Edward I, Edward II and Edward III from 1296 to 1340.

Dotted around the rest of the town are dozens of interesting houses which range in architectural style. Just outside the graveyard wall, for example, is the distinctive Court Hall parts of which date back to the 13th century and is a Grade I listed building. It’s also home to the town museum.


A short distance from St Thomas’ Church, you also find the 19th century well and next to that, the magnificent Armoury. A Grade II listed building, the west part is 14th century and the east part is 15th century. It takes its name from the time of the Napoleonic Wars when the Duke of Wellington’s troops were quartered there. At the end of the 19th century, Sir Robert Peel’s niece carried out some substantial rebuilding. Understandably, not far away is Magazine House and apparently, there’s even an old bear pit nearby. The Armoury was also once home to the weavers of the English Linen Company.


There’s a Methodist church in the town and also a famous tree under which John Wesley, the founder of Methodism, preached his last open-air sermon in 1790. Or at least, that’s the spot where he preached if not the actual tree. And to complete Winchelsea’s suite of spiritual provision, just outside the town is Greyfriars, the 14th century remains of a Franciscan monastery. Whilst not to be outdone, on the other side of town, the Blackfriars’ ruins have a 14th century cellar beneath them which includes drawings of 12 ships of the period, scratched into the surface.

Things to do

It’s fair to say that there’s not a massive amount of things to do in Winchelsea, and that’s part of its charm. The main pleasure is to be had from just wandering about and enjoying a parcel of Grade I and II listed buildings, pretty clapboard houses and stunning views. You’re only a mile from the sea and you can see cruise liners clearly from various streets. The museum runs regular cellar tours and of course, there are always great local walks, bike rides, Rye, and nearby Winchelsea beach.

Places to stay

Our top recommendation for places to stay is the Strand House. Oozing with historical charm to help get you in the mood, the hotel dates back to the 14th century. It’s been home to monks, as well as being a farm and a workhouse. It’s Grade II listed and has inglenook fireplaces, low oak-beamed ceilings, and four-poster beds.


By way of a footnote, if you’re in any doubt about pirates, bear in mind that in 1769, 13 prisoners were capitally convicted on an indictment for “felony and piratically”. These were Hastings pirates whose crime was that, in company with others (some of whom had not been captured and some of whom were dead), they attacked with “one cutter and four lugsail boats” (also known as hovellers) a Dutch hoy called Diege Sustures bound from “Roan to Havre and Amsterdam” on the 15 August 1768 not far from Beachy Head.  Not quite Winchelsea waters but I’d be interested to hear of any stories specifically relating to Winchelsea pirates.

If you like this post about Winchelsea in East Sussex, you may also like:

Top Things To Do In Rye

Rye Harbour to Winchelsea 15 km Cycle Ride

Visit Camber Castle near Rye (East Sussex)

Things To Do In Hastings, East Sussex

For more information: 

Cellar Tours:


The Strand House:

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