It is not easy to find the historical origins of the peoples of our region.
Archaeological remains have been found within the municipal term, corresponding to the Bronze Age, numerous fragments of Roman sigilata earth and Visigothic pottery whose mud contains small fragments of mica, characteristic of the clay of this zone.
But it is most probable that the origin of the present town is in the repopulation of the southern slope of the Sierra de Guadarrama, made by the city of Segovia in the 12th century.
The existence of Valdemorillo is documented since the year 1302, under the reign of Alfonso XI, when Segovia promulgated the ordinance in which were determined the limits of some of the lands located in the southern outskirts of Guadarrama`s mountain chain.
Valdemorillo is mentioned as part of Tierra de la Jara, with a more extensive municipal term than the present one that covered Villanueva de la Cañada, then called Despernada, part of Quijorna and other villages like Valmayor were within it also.
Valdemorillo is also mentioned in the book of the montería of Alfonso XI (1342) a work of reference for hunting lovers, and in which the term of Valdemorillo is described as abundant of forests and hunting, which seems to indicate a sparse population and limited farmland.
Likewise, the Archpriest of Hita, in his "Book of Good Love", quotes Valdemorillo, in the Battle of Don Carnal and Doña Cuaresma, in the verses 1,185, 1,186.
“Cabrones e cabritos, carneros y ovejas
Daban grande balidos, dizen destas consejas:
Sy nos lieva da aquí Carnal por las callejas,
A muchos de nosotros tiraran las pellejas.
Prados de Medellín, de Cánceres, de Troxillo,
La Vera de Plasencia, fasta Valdemorillo,
Toda la Serranía el presto mancebillo
alborozó ayna e fizo muy grand portillo”