Maidstone has an interesting cultural history leading the way in which life in England has changed from the system of serfdom through the Peasants Revolt of 1381.  Wat Tyler and radical cleric John Ball lead the way for the contingent from Kent to march upon London.  This started with the burning of court records and the opening of local gaols.  The rebels fought to end the system of unfree labour, labour at this time was tied to the land in a bond.  The uprising was also against the system of unfair taxes, which they sought to reduce.

Maidstone has the interesting local custom, which has survived from feudal times, whereby the Mayor has to lead the local annual swan round-up.

The local theatre, is named after the18th century writer William Hazlitt and offers a wide range of music, dance and theatre.  Buskers and street performers can be found in the town centre on a regular basis.

Maidstone Museum offers a great deal in the way of local history, looking at the brewing industry and distilling industry of which the gin production was around 5000 gallons per week.  Gin is still produced in Maidstone.

The Maidstone Fringe Festival and the Maidstone Arts Festival run during April/May and July with fabulous free events at the weekends in Jubilee Square.  This is full of music and dance, and the audience frequently sit in deck chairs in the sunshine to enjoy the occasion.

Maidstone also has the best nightlife in Kent with lots of bars, clubs and restaurants, which run into the early hours of the morning ensuring the fun never stops.  The town has been awarded a prodigious purple flag award for the safety of the town centre at night.