This name, with variant spellings Chaster and Chesters, is of English locational origin from Chester, the County town of Cheshire, or from any of the various smaller places so called including Little Chester, (Derbyshire), Chester le Street, (Durham) or Chesters, (Northumberland). The name, in all cases, derives from the Old English "Ceaster", a Roman fort, ultimately from the Latin "Castra Legionum", a legionary camp. Some of the earliest recorded spellings of Chester, (Cheshire), include Leggacaestir circa 730, Bede's "Historia ecclesiastica", and "Cestre" - "The Domesday Book, (1086)". The surname first appears on record at the beginning of the 13th Century, (see below). Other early recordings include William de Chestere, (Somerset, 1327) and John Chestre, (Warwickshire, 1366). Sir William Chester (1509-1595), son of a London draper, was Lord Mayor of London, 1560, M.P. for that city, 1563, and honourary M.A. Cambridge, 1567. The first recorded spelling of the family name is shown to be that of Richard de Cestre, which was dated 1200 - The Pipe Rolls of Lincolnshire, during the reign of King John known as "Lackland", 1199 - 1216. 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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