Henry II (1154-1189) started the great Castle of Dover and much of the masonry was brought by sea and landed at the Eastbrook Harbour. During the reign of King John, Henry’s youngest son, the English Barons invited the Dauphin of France to take over the throne. London and most of Southern England fell but Hubert de Burgh, the Constable of Dover Castle, held out. The French soldiers camped in the area of today's Laureston Place, known as Uphill and a long siege ensued. During that time, the French soldiers excavated a tunnel in order to invade the Castle, and it was said to start in the area now used as a sports field for St Mary’s school. Famously, Hubert was reported as saying: "I will not surrender; as long as I draw breath I will never resign to French aliens this Castle, which is the very key to the gate of England!" The French were eventually defeated.
Around Eastbrook harbour seafarers built cottages and sometime before 1291 Old St James Church - now called the ‘Tidy Ruin' - was built. Originally, the church consisted of a nave and a chancel but was extended in the reign of Edward II (1307-1327) to house the Courts of Admiralty and Chancery of the Cinque Ports. The Court of Lodemanage, to which Dover Pilots were responsible, was also held in the Church under the authority of the Lord Warden.
There is little evidence of what Dover looked like during this time, but adjacent to the old Church ruin is Hubert's Path. This is believed to be part of the ancient path up to the Castle from the Eastbrook harbour. It is said that the path was a continuation of Dolphin Lane that originally connected the centre of town with the Castle. In all probability, it was given that name as ‘Dolphin’ as in those days the word was used to describe a mooring ring or post to which ships were fastened.
The White Horse Inn, the town's oldest residence, is the only building remaining from the days when Dover's harbour was in this locality. Originally, the Inn was two cottages that were knocked into one, in 1365, to provide a home for the vergers of St James Church. Possibly, at this time St James Street, on which the White Horse Inn stands, started to develop. It became the main route out of Dover to Deal and climbed up Castle Hill via Uphill.
Towards the top of the hill the road was a dangerous place to traverse, almost enclosed by deep thickets and known as Tinker’s Close. At Uphill, a market developed where villagers from along the Deal road, would sell their produce there, as did travellers - or tinkers, as they were called. Renamed Upmarket, it did not have a Charter by which produce and sellers were regulated. Nonetheless, during times of plague, petulance or any other reason why the official regulated market was closed, the town’s fathers gave recognition to Upmarket and, no doubt, collected fees for so doing!
Since the time of the Romans, the sea had been receding, but in the late Middle Ages, the situation reversed. In order to protect the town an earth dam called the Wyke, was built from the Bench Street end of Snargate Street to the Eastbrook Harbour. This was paid for out of local taxes on profits from the Passage and fines metered out by the Court of Lodemanage on pilots and ship owners. A quay was laid behind the Wyke that effectively extended Eastbrook harbour and the council, not slow at seeing another possible source of income, levied a wharfage tax on those who used this quay. About 1424 the town's folk rebelled and petitioned the King, Henry VI. He responded with a Charter giving free wharfage to the people of Dover forever. This privilege, however, ceased about 100 years ago!
The Wyke created a little cove on the west side of the Eastbrook Harbour that was utilised by shipbuilders. Henry VI, in 1440, gave Dover another Charter giving these shipyards the monopoly of the Cinque Ports ship building industry. Profits were to be used for the maintenance of the harbour but were not enforced. By 1450, silt blocked the mouth of the Eastbrook harbour but a natural pool had formed below Archcliffe point, at the west end of the bay. Eastbrook was abandoned and this gradually was used as the harbour despite it being far from the town. However, shipbuilding flourished at the east side of the bay until 17th century.
During Medieval times, Dover had two parishes, St Mary’s on the west side of the river Dour and St James on the eastern side. The seafaring folk traditionally lived in St James Parish and when they moved westward, to the new harbour, they remained beholden to St James Parish. Further, the Dour was more serpentine in those days creating an isthmus into the east of what we now know as Market Square, thus the area was in the Parish of St James. As time passed, these lands became the source of bitter disputes between the two parishes as to which one should get the taxes!
Taxes paid for parish projects such as the Watch - the safety of the Ward. Dover was divided into twenty-one Wards and from the days of Edward the Confessor each of these Wards provided, for fifteen days a year, a fully manned ship for the King’s service as part of the Cinque Ports fleet. In return, the Cinque Ports were given many rights and privileges not found elsewhere in the country. By the time of Henry VIII, the Cinque Ports power was on the wane but the Ward system remained and the earliest record of these Wards dates from that time. It was recorded that only twenty Wards remained as one had ‘been overtaken by the sea.’ In the Parish of St James these were:
Mankind Ward: Today, St James Street on the east side of the Dour
Shingle Ward: The shore side of Townwall Street
Ball's Ward: Woolcomber Street area
Oxe's Ward: Under Castle Cliff in the area of the present swimming pool
Halvenden Ward: Approximately, where what now remains of St James's Street
Wolve's Ward: Stembrook area
Delf Ward: Around Hubert Place area
Upmarket Ward: Laureston Place area
Horsepole Ward: Ashen Tree Lane area
Castle Danes Ward: North along what is now Maison Dieu Road to Charlton village boundary.
In addition, Dereman's Ward: At the west end of the bay, where seafarers had built cottages near the new harbour