W. H. Bowles, in his "Records of the Bowles Family" published in 1918, believed that the Bowles first appeared in Kent when a branch of the Lincolnshire family arrived in Chartham in the 15th century. We have since learned that the name appeared in Kent in the 1200's, quite possibly having originated here and had spread widely throughout Kent within a century. That line appears to have even led to the Chartham line which Bowles referred to.

The earliest Boles record in Kent I have found so far is for a Simon Bole of Ickham, Kent who is mentioned in a land agreement which has been dated from between 1222 and 1238.  See The Boles of Ickham

In the next hundred years there were Bole, Boles, Bolle, Bolles, le Bole and de Bole throughout East Kent. The variety of names is due to this being the formative period for surnames in England.  During that period family names were not commonly used although the new Norman rulers were encouraging the practice to aid in record keeping. This makes it extremely hard to sort out the family lines with any confidence.  Added to that would be the possibility of the arrival in Kent of Bolles from Lincolnshire (see The Bolles of Swineshead). The Bolles of Chislehurst who descend from The Bowles of Bromley are accepted to have descended from that line.  Descendants of The Bolles of Deal have also long claimed that link but I have not independently researched it so I'll leave that proof to other web sites.  I can say that I have found references in the Sandwich area from as early as the 1200's and quite a few records in the 1400's and 1500's.  Deal was established in the late 1600's when it obtained its own charter and thus attained independence of Sandwich.  The origin of the Charles Bowles of Chatham line, which in turn led to the Bowles of Eltham, is not known to me.

However, from my research the Bowles of Kent story starts with The Boles of Ickham, leads to The Bolles of Chartham, who seem to have led to some of The Bowles of Chatham, with the possible exception of Charles, and has side roads off to The Boles of Canterbury, The Bowles of The Weald of Kent and of Ramsgate (see below) and to at least some of the Boles in Farnborough, Hythe, Sittingbourne, Herne, Reculver, Milton, Chislet, Whitstable, Manston, Fordwich, Boughton-under-Brean, Cranbrook, Woodchurch, Southwark, Seasalter, Sandwich, Appledore and Willesborough (See Misc. Bowles of Kent).  There are also links between the Bolles in Kent and The Early Bolles of London.

Click on the Map to see a larger version

Brenda Paternoster (nee Bowles), who currently lives in Kent has traced her branch of the Bowles family back to 1690 living in various villages south of Maidstone in the Weald of Kent as represented by the very general square on this map.  See Brenda's Family History site for information on her branch of the Bowles family.

I have just a little information on a boatman Thomas Bowles of Ramsgate, Kent

See also Bowles Marriages in Dover, Kent

Unknown references:

The following references have not yet been connected to any particular location in Kent.  An examination of the original document may solve that eventually.

The Calendar of Patent Rolls for Jan. 4, 1318 at Westminster documents a complaint by the Abbot of St. Augustine’s Abbey, Canterbury that a large list of men including a John Bolle had “attacked his dwelling place at Salmanston, placed fire against the door to burn the manor, broke his ploughs, carts and harnesses, cut up and felled his trees there and at Menstre in Thanet besieged Henry de Newenton, his fellow monk, in the Abbot’s dwelling place at Clyvesende, uproofed and wrecked his houses there and imprisoned the monk and later sold him for a sum of money as if he had been taken in time of war”.  I haven’t been able to discover what the issue of the time was or what faction John Bolle would have represented.  ref. 

In 1339 John Bolle of Kent signed a Certificate of Statute Merchant and Statute Staple with Elizabeth de Burgh, Lady of Clare before the Mayor of London.  ref.  This was basically an agreement under which Lady Clare invested some money in John Bolle's land and he repaid her over time from the profits of the land.  What is really interesting about this though is that Lady Clare was a first cousin of the King and one of the wealthiest women in England. On the same day in 1339, she signed nine of these certificates, all to men of Kent and these are the only ones which she was known to have signed as her household papers were preserved.  ref.  That puts John Bolle in some pretty high society.  ref.  It's also interesting that her father, Gilbert de Clare, earl of Gloucester and Hertford, had sent a Robert Bole over to Ireland to handle his interests there in 1291.  (ref. Patent Rolls of Edward I)

There is one very unhelpful (so far) reference for a Chancery Pleading between Edward Culpeper, Esq. and William Bolle regarding a tenement in Kent.  ref. 

More to come, this page is still developing.

Sources: 

The single greatest online source for medieval Kent documents is the Canterbury Cathedral Archives whose searchable online catalogues contain a wealth of Boles references.  The Centre for Kentish Studies and the East Kent Archives Centre both have extensive archives catalogues which are searchable online using The Kent Archives site.   The Kent Archaeological Society also has a lot of source materials online.  The A2A site provides a central way to search those archives as well as other archives all over England.  The Here's History Kent site has valuable background information including a fantastic collection of very early maps.