This name originated as a distinguishing nickname for a man from Chester in Cheshire. The placename, recorded as "Ceaster" in Early Anglo-Saxon Chronicles, and as "Cesre" in the Domesday Book of 1086, derives from the Olde English pre 7th Century "Ceaster", a Roman Fort (Latin "Castra", legionary camp), plus "mann", a man. One Richard de (of) Cestre, recorded in the Pipe Rolls of Lincolnshire, dated 1200, was the earliest recorded bearer of the name. The surname Chesterman is particularly well recorded in London church registers from the late 16th Century. The suffix "man", in this case, has augmentive force. On January 17th 1591, Ellyn, daughter of William Chesterman, was christened in St. Katherine by the Tower, London. Adam Chesternan, aged 19, who embarked from London on May 21st 1635, was one of the earliest recorded namebearers to settle in the New World Colony of St. Christophers in the Barbados. The first recorded spelling of the family name is shown to be that of William Chesterman, marriage to Katherine Linley, which was dated 1588, at St. Dunstan's Church, Stepney, London, during the reign of Queen Elizabeth I, known as "Good Queen Bess", 1558 - 1603. Surnames became necessary when governments introduced personal taxation. In England this was known as Poll Tax. Throughout the centuries, surnames in every country have continued to "develop" often leading to astonishing variants of the original spelling.

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