5 Essex Castles Worth Visiting: A Guide to the County's Hidden Medieval History

By Fire Pud the Dragon (Mythical Creatures and Castle Expert)

Essex does not have the greatest reputation for castles in the UK. But I think that is a disservice to the county, it is unfair, historically inaccurate - rather like the movie Braveheart - and since the author of The Good Knight series grew up in the seaside resort of Southend-on-Sea I feel duty bound to correct this inaccuracy for his honour.

The county has more medieval fortifications than most people realise, and the range of what survives is, when you know what you're looking at, genuinely extraordinary. From the largest Norman keep in Europe to a grass mound in a National Trust car park, each one tells a different story about what happened to the county after 1066 - and let's not forget that Essex was one of the seven traditional Anglo-Saxon kingdoms that made up the hepatarchy in early medieval England!

Over the years I have visited them all. Here are the five that I think you should know about.

1. Colchester Castle: The biggest Norman Keep in Europe

Let's start with the headline fact. Colchester Castle's keep measures 152 by 112 feet, the largest Norman keep by floor area in Europe. It makes the Tower of London look modest. And the reason it's so large is the most remarkable thing about it.

Construction began in 1076, just 10 years after the Norman invasion. It was acutally built on the foundations of the Roman Temple of Claudius, the largest Roman temple in Britain, which was dedicated to the Emperor Claudius after his death in AD 54.

The Normans didn't just build on top of a Roman site. They deliberately incorporated it, partly because the foundations were already there, partly because building on Roman ruins was an explicit statement of power. We are the new Romans. Look at our castle. William the Conqueror's biographer even compared him to Julius Caesar!

The Temple itself had its own dramatic history, when Boudica, Queen of the Iceni, led her revolt against the Romans around AD 60, the citizens of Colchester made their last stand inside the temple. They held out for two days before they all died a grizzly death.

What's there now: Colchester Castle houses a museum with archaeological collections of international quality covering 2,500 years of history, including the Fenwick Hoard, a stash of Roman jewellery buried to protect it from Boudica's army, Celtic coin hoards, Roman statues, medieval paintings, and Civil War armour. Guided tours take you down into the foundations where the Temple of Claudius is still visible. It is genuinely spectacular. Entry is charged.

2. Hedingham Castle: The best-preserved Norman Keep in England

Built around 1140 by Aubrey de Vere II, Hedingham Castle's keep stands 110 feet high with walls 12 feet thick at the base. The de Vere family held the castle for over 500 years and became the Earls of Oxford, one of the most powerful noble houses in medieval England.

The connection to national history is extraordinary. Robert de Vere, 3rd Earl of Oxford, was among the 25 barons who forced King John to sign the Magna Carta in 1215. The following year, King John took his revenge and besieged the castle. Later visitors included Henry VII, Henry VIII, who stayed in 1509, and Elizabeth I, who visited in 1561.

Inside the keep is a banqueting hall with a Norman arch spanning 28 feet, one of the largest of its kind in England. It is the kind of room that makes you understand, viscerally, why medieval power was expressed in stone.

What's there now: Today the castle is privately owned by direct descendants of the de Vere family and operates as a wedding and events venue, with open days featuring jousting, outdoor theatre, and history tours. When it's open, visit. It is the real thing.

3. Hadleigh Castle: The romantic ruin on the hill

Hadleigh Castle was begun around 1215 by Hubert de Burgh and later extensively refortified by Edward III during the Hundred Years War, primarily to defend the Thames Estuary against French raids. Edward III also used it as a royal residence, close enough to London to be convenient, dramatic enough in its setting to be impressive.

The castle fell into ruin over the following centuries. In the 1820s, the artist John Constable painted it, one of his most celebrated works, the ruins silhouetted against a stormy sky, and inadvertently made it famous.

The castle is still slowly moving. The clay beneath it has shifted for centuries, helping create the romantic silhouette that artists now love and makes it look so dramatic.

What's there now: Owned by English Heritage, Hadleigh Castle is a ruin in open countryside with no visitor facilities, no tea room, no gift shop, but with extraordinary 180-degree views over the Thames Estuary.

The barbican and two towers still stand. It is free to visit, set within Hadleigh Country Park, and genuinely beautiful. The absence of facilities is, depending on your disposition, either a drawback or entirely the point - there are some beautiful walks from Leigh-on-Sea train station.

4. Rayleigh Mount: The mound that started a town

This one requires a small adjustment of expectations. There is no castle at Rayleigh Mount. There is a mound. It is, however, a very impressive mound with an excellent history behind it. Children might not overly believe that there was ever a castle there, but love the views and is a great place to take your dog for a walk.

Built by Sweyn, High Sheriff of Essex, one of the most powerful men in post-Conquest England, Rayleigh was a classic motte and bailey castle that passed to the Crown in 1163 and was twice repaired in the later 12th century. The town of Rayleigh grew up around the castle, shaped by its presence, the street layout of the modern town still reflects the outline of the original bailey.

What's there now: Managed by the National Trust, Rayleigh Mount is a 50-foot motte with a moat and extensive bailey, offering views over the Crouch Valley and hosting summer open-air theatre.

There is a windmill nearby that is also worth a visit. Entry is free, but do check the opening times - I have never quite seen it open!

This is the one to take children to when you want to explain how castles worked without anyone needing to be particularly patient. The mound is climbable, the views are excellent, and the whole site takes about forty-five minutes, which is, for three children under 5 1/2, exactly the right length for a visit - the shops and cafes of Rayleigh are a short walkaway, so the kids can get a well-deserved strawberry milkshake for their exploring.

5. Pleshey Castle: The hidden one

Pleshey is the Essex castle that most people have never heard of, which makes it immediately the most interesting one on this list.

The impressive remains of this motte and bailey castle dominate the village of Pleshey. Pleshey became one of the great noble residences of medieval England. Its most famous resident was Thomas of Woodstock, son of Edward III, whose conflict with Richard II ended in arrest, imprisonment and a death that remains suspicious to this day.

The de Bohun family ruled here, and Eleanor de Bohun's husband, the Duke of Gloucester, was ambushed and killed with the connivance of his nephew Richard II. The de Bohuns were avenged three years later when the Duke of Exeter, implicated in the ambush, lost his head to a mob outside Pleshey's walls.

Medieval politics were a little more ruthless than their modern equivalent.

The castle still has an impressive 50-foot motte, moat, and extensive bailey covering most of the village. Much of the structure was demolished in 1629, but what remains gives an extraordinary sense of how dominant these fortifications once were.

What's there now: The earthworks are remarkable — the motte rises dramatically and the scale of the original fortification is clear. Pleshey Castle grounds are open to the public by appointment only, which means you need to plan ahead, but the village itself is extremely pretty and worth the trip regardless. Free to visit when open.

The Essex Castle Road Trip

The castles range from the internationally significant museum at Colchester to the appointment-only earthworks at Pleshey, tells the full story of what the medieval period built in Essex and what we've done with it since.

Between them, these castles tell almost the entire story of medieval Essex, conquest, rebellion, royal power, noble ambition, murders, invasion scares, civil war, and eventually decline. What survives today is only a fraction of what once stood here, but it is more than enough to fire a child's imagination.

Some we've preserved brilliantly. Some we've let quietly crumble. Some we've turned into wedding venues, which is, when you think about it, exactly what a medieval great hall was designed for.

Join Jack's Shield Wall — the free Good Knight newsletter — at thegoodknightbook.com/shield-wall. New members this month receive a free Guide to Medieval Insults. Several of which are available for use at Hadleigh Castle, where there is nobody within earshot. 🏰⚔️