Winchelsea only has a tiny population of 600 but boasts a huge and fascinating history.

When Edward I appointed people to find a new site for the town after the original town was destroyed, his commissioners settled on the hill of Iham, and Winchelsea as we now know it came into being. One story is that this road was therefore originally called Hiham Street, but then changed to Hiham Green to avoid confusion with the High Street. Either way, it’s an incredibly pretty place to live.

The ruined medieval church at Greyfriar's in WinchelseaThe ruined medieval church at Greyfriar's in Winchelsea (Image: Andrew Hasson)

RUINED MEDIEVAL CHURCH AT GREYFRIARS

In the early part of the 13th century, a brotherhood of Franciscans, or Grey Friars, established themselves in the town. They lasted until Henry VIII ordered the dissolution of the monasteries in 1536. The stunning ruins of the friary church, originally built before 1320, now sit in the private estate of Greyfriars, a Grade II Listed 19th century mansion on the edge of town. Access to visit is only available by prior arrangement through The Winchelsea Archeological Society tours, or by staying in the Herons Wood and Eagles Nest Wing of Greyfriars. 

 

Mariteau House on German StreetMariteau House on German Street (Image: Andrew Hasson)

MARITEAU HOUSE

Mariteau House is a Grade II Listed late 18th century mansion on German Street, one of the tallest buildings in town. It is now divided into five apartments. The building was known to locals as ‘Dizzy House’ because the owner, a Dr Ernest Skinner, ran the property as a private mental home.

 

The gravestone of Spike Milligan at the Church of St Thomas the MartyrThe gravestone of Spike Milligan at the Church of St Thomas the Martyr (Image: Andrew Hasson)

SPIKE MILLIGAN

The Irish comedian, writer, musician, poet, playwright and actor Spike Milligan is buried in the churchyard of St Thomas the Martyr, which dates from at least 1215. His epitaph, written in Gaelic, reads: ‘I told you I was ill.'

 

The New Inn on German StreetThe New Inn on German Street (Image: Andrew Hasson)

THE NEW INN

There was a time, in the 13th or 14th century, when Winchelsea’s population exceeded 6000 or so, more than ten times what it is today. In that time, it seems certain there would have been many inns catering to the citizens’ needs. Nowadays, there is just one remaining, the New Inn on German Street which boasts friendly staff and amazing food.

 

The Armoury in Castle StreetThe Armoury in Castle Street (Image: Andrew Hasson)

THE ARMOURY

The Armoury on Castle Street is a deceptive-looking building. Some of the interior dates back to the 14th century but, in the 19th century, it was covered with a new stone cladded shell, giving it a gothic look. At one time, it was one of the town’s pubs, The Bear Inn.

 

The Church of St Thomas the MartyrThe Church of St Thomas the Martyr (Image: Andrew Hasson)

CHURCH OF ST THOMAS MARTYR

Inside St Thomas’ Church are these fantastic carved tombs dedicated to Gervase Alard and his son Stephen, both of whom held the rank of Admiral of the Cinque Ports in the early 14th century. Gervase Alard was the first mayor of Winchelsea.

 

The Strand GateThe Strand Gate (Image: Andrew Hasson)

THE STRAND GATE

The Strand Gate, dating from the 13th century, is a scheduled Ancient Monument. It was one of the four gates guarding the town from invaders.

 

Prescott House, the former home of novelist Ford Madox FordPrescott House, the former home of novelist Ford Madox Ford (Image: Andrew Hasson)

PRESCOTT HOUSE

Prescott House once belonged to the English novelist and poet Ford Madox Ford – famous The Good Soldier and Parade’s End tetralogy – who lived here in the early 1900s. His birth name was actually Ford Madox Hueffer, but he changed it after the Great War, when Germanic-sounding names fell out of favour, much like our own royal family did in in 1917. Another well-known novelist Joseph Conrad, author of Heart of Darkness, lived over the road and they could often be seen together enjoying a drink on the front step.

 

Tower House, the former home of Dame Ellen Terry next to The Strand GateTower House, the former home of Dame Ellen Terry next to The Strand Gate (Image: Andrew Hasson)

TOWER HOUSE

One of the 19th century’s most famous actresses, Dame Ellen Terry, lived for ten years in Tower Cottage next to Strand Gate. She was considered the leading Shakespearean and comic actress in Britain and people would travel to Winchelsea from all over the country in the hope of seeing her.

 

The New Gate on Wickham Rock LaneThe New Gate on Wickham Rock Lane (Image: Andrew Hasson)

THE NEW GATE

Built in the 13th century, the New Gate lies a little over half a mile outside the town, on Wickham Rock Lane and was once the only way out of Winchelsea by land. It is one of the three remaining medieval defensive gates to the town, from the original four. At the start of the film ‘Mr Holmes’, you see the lead actor Sir Ian McKellen being driven through this gate.

 

Jennifer SutherlandJennifer Sutherland (Image: Andrew Hasson)

LOCAL RESIDENT JENNIFER SUTHERLAND
 

Winchelsea resident Jennifer Sutherland: ‘What’s great about Winchelsea is the community. I can go for a walk to The Little Shop to get some milk, a ten-minute round trip, and I can be half an hour because I meet so many people on the way that say, “Hello, how are you?”, or “By the way, can you come and help sell raffle-tickets?” I always come home with a job! It’s a very caring place and there are more than 40 societies ranging from a wine society, a literary society to a garden society.’

Jonathan MurphyJonathan Murphy (Image: Andrew Hasson)

LOCAL RESIDENT JONATHAN MURPHY

Winchelsea Resident: Jonathan Murphy: ‘This place is fantastic because when you walk around it at any time or any day, you always see something you haven’t noticed before. All the buildings go back so many years and there’s a great community here. We have a pub, we have a shop and we have a school. There’s no supermarket, but I don’t think anyone would want them to build one here. I have to say, life in Winchelsea is pretty good.’