This unusual surname is of Anglo-Saxon origin, and is a locational name from some minor, unrecorded, or now "lost" place called Ollerhead or Owlerhead, believed to have been situated in the Yorkshire/Cheshire area because of the high incidence of early surname recordings from that region. The component elements of the placename are the Olde English pre 7th Century "alor", alder (tree), written as "owler" in many dialects, with the Olde English "heaford", head, used in various transferred senses such as "headland, summit, upper end, source of a stream"; hence, "headland where alders grew". Owlerton near Sheffield in Yorkshire, and Ollerton in Cheshire and Nottinghamshire, also have the Olde English "alor, owler" as their initial element. An estimated seven to ten thousand villages and hamlets are known to have disappeared in Britain, many as a result of the enforced clearing of rural settlements to make way for sheep pastures at the height of the wool-trade from the 15th Century on, and also due to such natural causes as the Black Death of 1348, in which an eighth of the population perished. Recordings from English Church Registers include: the christening of Robert Owlerhead, an infant, on March 14th 1577, at St. John the Baptist, Chester, Cheshire; the marriage of Ann Ollerhead or Owlerhead and John Sykes on December 15th 1588, at Rotherham, Yorkshire; and the marriage of Mary Ollerhead and William Davies on December 31st 1695, at Frodsham, Cheshire. The first recorded spelling of the family name is shown to be that of Elizabeth Owlerhead, which was dated October 22nd 1564, marriage to Edward Spooner, at Rotherham, Yorkshire, during the reign of Queen Elizabeth 1 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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