This uncommon name is of Anglo-Saxon origin, and has two possible sources. Firstly, it may be a locational surname from some minor, unrecorded, or now "lost" place believed to have been situated in Warwickshire, and called Checkland; the number of recordings of the name, and its variants, in Warwickshire and the surrounding counties are indicative of a habitational name. An estimated seven to ten thousand villages and hamlets are known to have disappeared since the 12th Century, due to such natural causes as the Black Death of 1348, in which and eighth of the population perished, and to the effects of the numerous Enclosure Acts since the 15th Century. The place would have been named with the Olde English pre 7th Century elements "Ceacca", a personal name also found in the placenames Checkley and Checkendon, and "land", estate, landed property; hence, "Ceacca's land". Secondly, the modern surname Checklin may be a variant form of the mainly Kentish topographical name Chalkland, from the Olde English "cealc", chalk, limestone, and "land", as before, for someone who lived on or by "chalk land". The modern surname forms from both of these sources range from Chalkland, Chalklin and Chalklen, to Checkland, Checklon, Checklin, Chacklin and Chicklin. Among the recordings of the name in Church Registers is that of the marriage of Goodith Checklin and Vincent Hewitt, at Walsgrave on Sowe, Warwickshire, on November 1st 1641. The first recorded spelling of the family name is shown to be that of Katherine Chalkelyn, which was dated August 10th 1596, marriage to Tim Merick, at Tonbridge, Kent, 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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