In ancient times being 'free' of a town or city meant that someone could trade there without paying the tolls that would be charged to an outsider. In the case of Richmond, the Freemen were those who were members of the town's thirteen ancient trade guilds. Guild membership normally followed the successful completion of an apprenticeship, although exceptionally it could also be by patrimony (the admission of the eldest son of a Freeman) or by redemption (paying a fee). Before the Municipal Reform Act of 1835, only the Freemen of Richmond were eligible to elect Council members, who themselves had to be Freemen. The town occasionally awards the Freedom of Richmond for some special contribution or achievement. The first recorded example of this was in 1725 when Francis Nicholson, Captain General and Governor of South Carolina in America was granted the Freedom of Richmond. Born in the Swaledale village of Downholme and probably educated at Richmond Grammar School, he had a remarkable career as one of the most important Englishmen in the history of the American colonies, and also devised the town plan of Annapolis, state capital of Maryland.

As well as occasionally bestowing Freedom on highly-regarded individuals, the town has granted Freedom to a number of military units with whom it has had close ties, allowing them to march through the town on ceremonial occasions with swords drawn, bayonets fixed, drums beating, bands playing and colours flying. These units are the Green Howards Regiment, Royal Corps of Signals, the RAF Regiment and the Company of the frigate HMS Richmond. Sometimes a special Testimonial is awarded to an organisation instead, as to the Duchess of Kent Military Hospital and the Infantry Training Centre. (Thanks to Jane Hatcher, who contributed this article).

In recent years the Freedom of Richmond has been bestowed upon Baroness Harris of Richmond (2004), Katherine Mary Carr (2004), the Royal Military Police (2006), Sylvia, The Lady Crathorne (2007) and the 2nd Battalion the Yorkshire Regiment (2008), John Blenkiron JP (2010), Pamela and Roy Cross(2011), Margaret Emmerson (2011) and The 1st Close Support Batallion Royal Electrical and Mechanical Engineers (2012)