The town's proximity to El Escorial has meant that many illustrious figures from history have passed through Valdemorillo.
It is claimed that, on 2 February 1575, members of the delegation transporting the mortal remains of Emperor Charles V to El Escorial spent the night in Valdemorillo.
This significant event could well be the reason that the town's annual fiestas are celebrated on the 2nd and 3rd of February.
It is also reported that the Spanish Prince Carlos I and Princess Isabel of Portugal stayed here during King Phillip II's final journey to El Escorial.
Historical documents from 1570 indicate the existence of two inns along the old route connecting Toledo and Segovia. They were located on the slopes of the mountain, in what is today the modern residential area of Pino Alto.
The proximity of the royal hunting grounds surrounding El Escorial meant that hunting was prohibited around Valdemorillo to protect the royal game. Today, it is still possible to see some of the old pillars marking this no-hunting area.
This was hugely damaging for farming in the local area, particularly for the vineyards, as can be seen in the statements and reports by the town's residents at the time.