Recorded as Traylen, Trayland, Trailand, Traylin, and Trayling, this unusual surname is of early medieval English origin. It is locational from what is thought to be a now "lost" village situated in the county of Essex near to the towns of Great Dunmow and Saffron Walden, and on the borders with Cambridgeshire and Hertfordshire. An estimated seven thousand medieval villages of the British Isles are known to have disappeared since the 14th century. The causes are various and include disasters such as the plague known as the Black Death of 1348, civil war, changes in farming practices, urbanisation, and especially the enforced "clearing" of settlements to provide for sheep pastures during the 15th to the 18th centuries. Early examples of the surname development include Jane Trayland of Essex in 1629, Anne Trailand of Suffolk in 1651, Daniel Trayelan of Essex in 1655, Samuel Traylen at Toppesfield, also Essex, in 1718, and Jonathon Trayling, a witness at St Brides church, Fleet Street, in the city of London in 1721. The placename and hence the later surname means "tree land", which may have described an area of dry land on a marsh covered by trees, or even land held by tree people, perhaps a reference to fen dwellers who lived in houses on stilts. The derivation is from the Old English pre 7th century word "treow", and "landa", and island or land. Throughout the centuries, surnames in every country have continued to "develop" often leading to astonishing variants of the original spelling.

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