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The area has been occupied since the Palaeolithic era, as attested by finds from the quarries at Swanscombe. The Medway megaliths were built during the Neolithic era. There is a rich sequence of Bronze Age, Iron Age, and Roman era occupation, as indicated by finds and features such as the Ringlemere gold cup and the Roman villas of the Darent valley.

The modern name of Kent is derived from the Brythonic word Cantus meaning "rim" or "border". This describes the eastern part of the current county area as a border land or coastal district. Julius Caesar had described the area as Cantium, or home of the Cantiaci in 51 BC.

The extreme west of the modern county was occupied by Iron Age tribes, known as the Regnenses. It is possible that another ethnic group occupied what is now called The Weald and East Kent. East Kent became a kingdom of the Jutes during the 5th century and was known as Cantia from about 730 and as Cent in 835. The early medieval inhabitants of the county were known as the Cantwara, or Kent people. These people regarded the city of Canterbury as their capital.

In 597, Pope Gregory I appointed Augustine as the first Archbishop of Canterbury. In the previous year, Augustine successfully converted the pagan King Æthelberht of Kent to Christianity. The Diocese of Canterbury became Britain's first Episcopal See and has since remained Britain's centre of Christianity.

In the 11th century, the people of Kent adopted the motto Invicta, meaning "undefeated". This naming followed the invasion of Britain by William of Normandy. The Kent people's continued resistance against the Normans led to Kent's designation as a semi-autonomous County Palatine in 1067. Under the nominal rule of William's half-brother Odo of Bayeux, the county was granted similar powers to those granted in the areas bordering Wales and Scotland.

During the medieval and early modern period, Kent played a major role in several of England's most notable rebellions, including the Peasants' Revolt of 1381, led by Wat Tyler, Jack Cade's Kent rebellion of 1450, and Wyatt's Rebellion of 1554 against Queen Mary I.

The Royal Navy first used the River Medway in 1547. By the reign of Elizabeth I (1558–1603) a small dockyard had been established at Chatham. By 1618, storehouses, a ropewalk, a drydock, and houses for officials had been built downstream from Chatham.

By the 17th century, tensions between Britain and the powers of the Netherlands and France led to increasing military build-up in the county. Forts were built all along the coast following the raid on the Medway, a successful attack by the Dutch navy on the shipyards of the Medway towns in 1667.

The 18th century was dominated by wars with France, during which the Medway became the primary base for a fleet that could act along the Dutch and French coasts. When the theatre of operation moved to the Atlantic, this role was assumed by Portsmouth and Plymouth, with Chatham concentrating on shipbuilding and ship repair. As an indication of the area's military importance, the first Ordnance Survey map ever drawn was a one-inch map of Kent, published in 1801. Many of the Georgian naval buildings still stand.

In the early 19th century, smugglers were very active on the Kent coastline. Gangs such as The Aldington Gang brought spirits, tobacco and salt to the county, and transported goods such as wool across the sea to France.

In 1889, the County of London was created and the townships of Deptford, Greenwich, Woolwich, Lee, Eltham, Charlton, Kidbrooke and Lewisham were transferred out of Kent and in 1900 the area of Penge was gained. Some of Kent, notably Dartford, is contiguous with Greater London.

During World War II, much of the Battle of Britain was fought in the skies over the county. Between June 1944 and March 1945, over 10,000 V1 flying bombs, known as "Doodlebugs", were fired on London from bases in Northern France. Many were destroyed by aircraft, anti-aircraft guns, and barrage balloons, yet both London and Kent were hit by around 2,500 of these bombs.

After the war, Kent's borders changed several more times. In 1965 the London boroughs of Bromley and Bexley were created from nine towns formerly in Kent. In 1998, Rochester, Chatham, Gillingham, and Rainham left the administrative county of Kent to form the Unitary Authority of Medway. During this reorganisation, through an "apparent" administrative oversight, the city of Rochester lost its official city status.

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