The Drummonds take their name from Drymen or Drummond in Stirlingshire. Sir Malcolm Drymen or Drummond fought for Robert the Bruce at Bannockburn, greatly contributing to Bruce's victory by strewing the battlefield with spikes to disable the English cavalry. The Drummond motto, "Go Carefully" is an allusion to this.
In the 14th century John Drummond became John Drummond of Stobhall, still the present Earls home. The Barony of Drummond was created in 1488 in favour of Sir John Drummond and in 1605 the 4th Lord Drummond was created Earl of Perth.
The Drummunds were loyal supporters of the Stewart. James, the 4th Earl was appointeed Lord High Chancellor of Scotland in 1684. On the accession of King James VII he openly declared himself a Roman Catholic. He was made a founder member of the Knight of the Order of the Thistle on its revival in 1687, as was his brother Lord Melfort, and made Duke by King James after his flight to France. In the Jacobite rising of 1715 the 2nd Duke of Perth commanded the Jacobite cavalry at the Battle of Sheriffmuir while the 3rd Duke was one of the principal Jacobite leaders in the rising of 1745.