[1] The oak is linked with a legend of Owain Glyndŵr, the last native Welshman to hold the title Prince of Wales (Welsh: Tywysog Cymru).

His route of march was blocked by the king's men on 21 July so Owain climbed the Shelton Oak to view the progress of the Battle of Shrewsbury, some 3 miles (4.8 km) distant.

[6] During the early 19th-century a plaque was erected at the site that read: "On July XXII AD MCCCCIIII OWEN GLENDWR ascended this Tree to reconnoitre, on his march to Shrewsbury, to join the daring Hotspur, against King Henry IV; but, finding his friends were defeated, returned from this spot into Wales" (the date and year stated here, 22 July 1404, are not those of the actual battle).

A report from 1878 suggests that the hollow trunk of the Shelton Oak was by then large enough for eight people to dance a quadrille within it.

[8] A second acorn from the tree was grown into a sapling and planted at The Elms in Shrewsbury by Dr Charles Waring Saxton on 5 February 1880.