There are several explanations and hence origins, for this English surname. Apparently recorded in a number of overlapping spelling forms including Winchcomb, Winchcombe, Winscombe, Winscomb, Wincom, Winsom, and Winsome, the name is almost always locational. As such the origination is either the ancient village of Winchcombe, meaning "remote valley", in the county of Gloucester, a place which is recorded Wincelcumba, in the Anglo-Saxon Chronicles of the year 816, or from Winscomb, a parish of the same meaning, in Axbridge, Somerset. Locational surnames are usually "from" names. That is to say names given to peiople after they left their original homesteads and moved elsewhere. Spelling being at best erratic and local dialects very thick, lead to the development of "sounds like" recordings. Another explanation for at least some of this surname spellings, is from the Olde English pre 7th century word "winsom" meaning attractive or lovely, and used as an early baptismal name. This is probably the explanation for the earliest surname recording of Matildla Winsom, in the Hundred Rolls of the county of Huntingdon in 1273, with William Winscombe being recorded in Somerset in 1316. Other examples include: John Winchcombe who married Elizabeth Dorsone at St Botolphs Bishopgate, in the city of London, on April 5th 1608, and Henrie Winchcomb who married Elizabeth Miller, at St Martins in the Field, Westminster, on November 20th 1639.

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