After the defeat of Charles' Royalist army at the hands of Oliver Cromwell's New Model Army in the Battle of Worcester, the King fled with Lord Derby, Lord Wilmot and other royalists, seeking shelter at the safe houses of White Ladies Priory and Boscobel House.

From White Ladies, Richard Penderel led Charles in an unsuccessful attempt to cross the Severn near Madeley, Shropshire.

[3] The Penderels and Colonel Careless employed coats of arms depicting an oak tree and three royal crowns, differentiated by colour.

The field in which the tree stands is owned and farmed by Francis Yates Partners, who allow the public access along a path from the garden of the house.

The tree standing on the site today is not the original Royal Oak, which is recorded to have been destroyed during the seventeenth and eighteenth centuries by tourists who cut off branches and chunks as souvenirs.

Three third generation descendants of the Royal Oak have been ceremonially planted nearby: Saplings, certified as grown from the Son's acorns, are available from the English Heritage shop at Boscobel House.