Like many counties in the South of England, the foundations laid by the Romans are easy to trace. After the Romans left, much of the region was settled by Germanic tribes, the descendents of whom established Canterbury as the main city. Throughout the medieval period Kent has an association with rebellion and resistance, starting with strong opposition to the Norman invasion of 1066, and including the Peasants' Revolt of 1381 and Wyatt’s Rebellion of 1554 against Queen Mary I.

The proximity of Kent’s coastline to that of continental Europe meant that it became a hotbed for activity in two areas: smuggling and the wars with France, with Medway becoming of key naval importance. Even though Plymouth and Portsmouth outgrew Medway in significance, an amount of military bases remained, with Chatham still being home to the Corps of Royal Engineers. During the Second World War, much of the Battle of Britain was fought in the skies of Kent and it took a heavy brunt of damage from V1 and V2 rockets that fell short of London.

The growth of London in the past 200 years has meant constant reorganization and defining of Kent’s boundaries, with the most recent change being the establishment of Medway as an independent unitary authority in 1998.