Neolithic finds have revealed the earliest occupation of the area; and the Romans have left their mark also: the road through the town and evidence of villas. The Normans set up a shire moot, and religious organisations established an abbey at Boxley, as well as hospitals and a college for priests. Today’s suburb of Penenden Heath became a place of execution in medieval times.

Maidstone’s charter as a town was first confirmed in 1549; although briefly revoked, a new charter in 1551 created the town as a borough. The town’s charter was ratified in 1619 under James I, and the coat of arms, bearing a golden lion and a representation of the river, was designed (in heraldic terms: “or, a fes wavy azure between three roundels gules, on a chief gules a leopard passant gardant or”). Recently these arms were added to by the head of a white horse (representing Invicta, the motto of the county of Kent), a golden lion and an iguanodon. The iguanodon relates to the local discovery in the 19th century of the fossilised remains of such a dinosaur : The remains are now displayed in the Natural History Museum in London.

During the Civil War a battle took place here in 1648, resulting in victory for the Parliamentarian forces. Andrew Broughton, who was Mayor of Maidstone in 1649 (and also Clerk to the High Court of Justice) was responsible for declaring the death sentence on Charles I, and today a plaque in Maidstone Town Centre memorialises Andrew as ‘Mayor and Regicide’ (a killer of kings).

Maidstone has had the right to a town gaol since 1604; the present prison lies north of the town centre and was completed in 1819. Army barracks have been a feature of the town since 1797, when the first was built. The present Invicta Barracks is home to the Royal Engineers 36 Engineer Regiment, which includes two Gurkha field squadrons.

From an economic point of view, Maidstone’s history has developed around the river, and also the surrounding countryside. Paper mills, stone quarrying, brewing and the cloth industry have all flourished here. The paper maker James Whatman and his son invented wove paper (Whatman paper) at Turkey Mill from 1740, an important development in the history of printing.