This interesting and unusual name, with spellings Jackway, Jackaway, and Jackways, is of post medieval English topographical origins, although curiously the surname probably refers to a Frenchman! It describes somebody who dwelt by by Jack's road wherever that was. The derivation being from the Old French personal name "Jacques" and the Old English, pre seventh Century word "weg", meaning a way" or road, a road owned by Jacques or perhaps passing his house. When surnames were created from around the 13th century onwards, one of the easiest means of identifying people was to call them by a local physical feature.This could be something simple like "East", implying one who lived to the east of the village, or Townend for a dweller at the end of the township, or Way or Road themselves. This particular name seems to be West Country for it is in the early surviving Gloucestershire church registers that most examples are to be found. These examples include Marie Jakway, who married Thomas Web on September 28th 1624, at the village of Leonard Stanley, Gloucestershire, whilst on November 27th 1628, Richard Jakeway married Mary Hiron at Chipping Campden. Later in October 1805, the year and month of the battle of Trafalgar, Mary Jakeways married Philip White at St. Leonard's church, Shoreditch, London, on the 31st of the month. The first recorded spelling of the family name is believed to be that of Isabell Jackway, married at St. James church, Clerkenwell, London, on January 24th 1612. This was during the reign of King James 1st, of England and V1 of Scotland, 1603 - 1625.
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