This is a locational name 'of Chesterfield' - a town in Derbyshire, so called from the Olde English pre 7th century 'ceaster' meaning 'a Roman Fort' and 'feld' - 'open country'. The name was originally given to one residing in open country by old Roman fortifications. It is first recorded as a surname towards the end of the 14th century. One Thomas Chesterfield (deceased c. 1451) was Canon of Lichfield (Staffordshire). In 1691, his 'Chronicle of the Bishops of Lichfield down to 1347' was published posthumously. The first recorded spelling of the family name is shown to be that of Robertus de Chesterfield, which was dated 1379, in the Poll Tax Records of Yorkshire, during the reign of King Richard 11, known as Richard of Bordeaux, 1377-1399. 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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