Hugh de Caly, the son of Osbert de Caly, married Agnes de Hemstede. Besides Owby and other lands in Norfolk, he owned a quarter of a knight’s fee at Richmond in Yorkshire. In 1268-9 he and his wife made a gift to the monks of Walsingham. He left money for the monks at St Helen’s, Norwich, to sing masses for his and Agnes’ souls: the monks were released from this obligation in 1350.
Hugh and Agnes had two sons:
- Sir William Cayley, Lord of Owby, Suffield and Hecham in Norfolk (he sold Hecham in 1316-7).
- John de Caly, who was recorded in 1303 as holding a knight’s fee at Staincliffe in the West Riding of Yorkshire
Sir William Cayley’s son John de Cailly was sheriff of Norfolk and Suffolk and keeper of Norwich Castle from 1331 to 1336. There are some uncertainties about the family tree from then until the late 16th century, and firm dates are for a period largely nonexistent: there were a succession of Johns and Williams, and it is not entirely clear how many generations there were. What follows is a somewhat conjectural attempt at a reconstruction of the line of descent.
It is likely that John de Cailly had two sons:
- William Cayley, who lived in Norfolk, married Alice Braose, and had two daughters:
- Eva Cayley, his main heir, who married Edmund Clipsby (Edmund thus inherited William Cayley’s main estates, and he assumed the arms of the Cayley family)
- Agnes Cayley, who married John Harslike, a Norfolk landowner.
- John Cayley, who held three knights’ fees in the Owby area of Norfolk, but by the end of his life had settled at Normanton in Yorkshire.
John Cayley probably had three sons:
- Hugh Cayley, who may be the Hugh Cayley fined at Macclesfield Hundred Court in 1368 for causing an affray, and who died childless
- William Cayley, who lived at Normanton, and whose daughter Jennet Cayley married John Lake, whose descendants were a prominent Normanton family
- John Cayley, who probably had two sons:
- another John Cayley who died childless
- Edmund Cayley, who had homes at Thormanby and York.
Edmund Cayley had two sons:
- the younger, another John Cayley, was a priest at Thormanby (the Cayleys had the advowson of this parish – the right to appoint the priest)
- the older, William Cayley, lived at Thormanby and inherited the Cayley’s Yorkshire lands.
William Cayley’s son John Cayley lived at Malton and had three sons:
- Edward Cayley, his main heir, who may have died in or before 1561, when his elder son was granted the advowson of Thormanby
- William Cayley, another priest at Thormanby
- Lawrence Cayley
Edward Cayley had two sons, and we start now to be on firmer ground, with some definite dates:
- William Cayley of Thormanby, who married Joan Gouldthorp, the daughter of a wealthy merchant of York, Richard Gouldthorp, who was Mayor of York in 1588. William died in 1586, and Joan in 1618.
- Richard Cayley
William Cayley had two sons:
- Edward Cayley, who purchased lands at Brompton-by-Sawdon, inland from Scarborough, where the main Cayley line was to be based. He married Anne Walters, daughter of William Walters of Cundall, and died at Brompton in 1642. His wife had died two years earlier, in 1640. In 1630 he was one of many gentry invited to accept a knighthood on the coronation of Charles I: this would have carried the obligation to pay for a troop of horse if the king wished. Edward Cayley refused the honour, but had to pay a fine of £25 instead. This was a fairly common way for new monarchs to raise funds.
- James Cayley who lived at Thormanby. He was a royalist in the English Civil War and in 1646 he had to pay a fine to the Parliamentarians to retain his lands. He married Mary Bell, daughter of Ralph Bell of Sowerby. He had four sons. Three – Edward Cayley, Peter Cayley and Matthew Cayley – died fighting under Prince Rupert for Charles I in the Battle of Marston Moor, 2 July 1644. This was the largest battle of the Civil War, and their victory gave the Parliamentarians control of the North of England. The fourth son, Richard Cayley, survived the battle and played a key role in the negotiations which preserved his father’s lands in 1646.