I am working on a theory that many of the Bowles in this region were the descendants of the family of Roger de Busli, one of the main Norman Lords that assisted William of Normandy's conquest of England in 1066.  I'm not quite ready to publish my research yet but I believe I can, if not prove, at least demonstrate a strong likelihood that the de Busli line spread from Yorkshire to Bedfordshire and then on to Hertfordshire and other counties.  There will be more on that yet to follow.

I also have some new research on the Bowles of Wallington, Herts (and Baldock, Herts even earlier; see below) an armorial family which I believe I can connect to The Bolles of Swineshead line which potentially might indicate a connection between that famous line and the Roger de Busli line.  Again though that research is not quite ready to publish as it is also tied up with my research into the de Busli line of descent.

There was also a Bole family at Hertford and the Carrington Bowles line lived at Myddelton House near Waltham Cross, Herts just about on the Middlesex boundary.

One line that I can publish at least my initial research on is The Bowles of Great Gaddesden, Herts.  This line travelled on to London, to the Bahamas, to Charleston, South Carolina and to Saskatchewan, Canada.

Baldock

John Bowlys was already of Hertfordshire in 1510 when he made a debt claim against four others.  ref.  He was a Commissioner of the Peace for Herts in 1522.

Baldock is a parish and town comprising an area of nearly 144 acres.  It was in the possession of the Knights Hospitallers on Sept. 18, 1522 when Thomas Docwra, the Prior of the Hospitaller's house of St. John of Clerkenwell, granted a lease on the manor of Baldock to John Bowles for a term of 21 years "with all the rents, perquisitions of court, view of francpledge, and profits of fairs and markets for an annual rent of £13". 

This document held at Hertfordshire Archives and Local Studies  refers to a lease held by John Bowles of Baldock going back to 1522.

He was one of the Commissioners appointed in 1523 to collect the Royal Subsidy in Herts for 4 years  In 1538, the Vicar of Baldock parish was under the patronage of John Bowles, Esq. 

An inquisition and post mortem was performed on July 3, 1543 after the death of John Bowles and is available at the Hertfordshire Archives ref.  His cousin, Thomas Bowles, was found to be the next heir to the property which is listed as "the Manor and rectory of Norton; Manor of Montfitchets in Wallington and Clothall; land in Wallington; land in Great Offley called Westbury Wood."    John Bowles' Will is available at the National Archives  ref.

John Bowles was High Sheriff of Hertfordshire in 1530 and 1543 and Thomas Bowles held the position in 1576 and 1601. He was succeeded in 1602 by Sir Edward Denney of Waltham Abbey who was also the landholder of Tralee and much of county Kerry, Ireland.

The Hertfordshire Archives also have a lease dated Apr. 7, 1660 between Thomas Bowles of Wallington, Esq. and Thomas Bowles, his son, involving their interest in the Manor of Nortonbury and property at Norton, Baldock and Willian.  ref.

Wallington

under construction

There are claims on several family trees online that the Bowles of Wallington were a branch of The Bolles of Haugh.  That is based on John Bowles of Wallington be the same person as John Bolle and Katherine Haugh's 4th son John Bolle.  So far I haven't been able to either prove or disprove that theory.

Hertford

The Town of Hertford itself was granted a charter by Queen Mary on Feb. 17, 1553/54 with 15 burgesses including a Thomas and Nicholas Bole. 

At the Church of All Saints, Hertford there is a memorial to members of the Carrington Bowles Family of Myddelton House which reads:

Daniel Garnault of Bull's Cross, Enfield, in the county of Middlesex, Esq. departed this life the 14th day of May 1809, aged 36 years.

Also Mrs. Ann Bowles, wife of Henry Carrington Bowles of the same place, Esq. and only sister of the said Daniel Garnault, Esq. died July 27th, 1812 in her 41st year.

Also Garnault Bowles, third and youngest son of the said Henry Carrington, and Ann, his wife, who died July 4th 1819 in his 8th year.

Also the above named Henry Carington Bowles of Myddelton House, Enfield, Esq. F.S.A. who died 30th June, 1830, in the 67th year of his age.

Likewise Henry Carington Bowles, of Myddelton House, Enfield, Esq., eldest son of the above, and many years a magistrate for the County of Middlesex who died 11th March, 1852 aged 51 years; and likewise John Bowles, Esq., the second and last surviving son of the said Henry Carington and Ann Bowles, who died May 25th, 1853, aged 44 years.

There is also a brass on the floor near the reading desk which reads: