One of the most striking aspects of the Sierras de las Villuercas is the concentration of places of archaeological interest. Their chronological correspondence with each of the stages of their history affirmes that the presence of man in these lands has been continuous from the earliest times to the present day.
Discoveries of stone tools from the Middle Pleistocene at the Rañas of Cañamero and Alía constitute the first and earliest examples of the presence of groups of Palaeolithic hunter-gatherers. This way of life was transformed with the appearance of the first sedentary communities of shepherds and farmers from the Neolithic, who were responsible for the construction of the earliest megalithic monuments, such as those erected at La Nava of Berzocana or the Cancho del Fresno of Cañamero.
These imprecise reflections of the expression of megalithism in Extremadura were characterised towards the western part of the region by small constructions with a peculiar and rare complement, decorated menhir statues. These primitive anthropomorphic representations are characteristic of the anthropocentric vision of the inhabitants of the last Chalcolithic stage, which is when the first settlements appear in this craggy landscape.
In the lower strata of the settlement on the hill of the Castle of Cañamero, the presence of the first Chalcolithic metalworkers is shown by a collection of tools, mainly copper. For these villages the surrounding territory was crucial and many cave paintings and engravings can be found in the rocky shelters. One of these privileged places is the River Ruecas, where all along its course from the Madrastra Cave or the Cancho de la Burra to the Risco del Citolar there are a dozen, containing the most varied examples of the Schematic Cave Art of the Chalcolithic period, with recurrent themes of hunting and grazing. One of the most spectacular places is the cave known as the Cueva Chiquita or Cueva de Álvarez, which is the first of the shelters of the long list of documented sites with this type of manifestation in Extremadura and a true prehistoric sanctuary.
Outside this valley, schematic figures are abundant on all the mountain chains, especially in shelters and small caves. Especially relevant ones because of their complexity and beauty include those of the Risco de Paulino, El Cancho del Reloj, and the Paso de Pablo, where the figures are moreover infraimposed on a rich collection of fauna including the black silhouette of a stag, which is probably the only sign of the presence in the district of hunters of the Epipalaeolithic, the ancient artists and exponents of what is known as Levantine Art.
During the Bronze Age the caves continued to be used as occasional refuges by shepherds and hunters, who were always numerous in these sierras as can be surmised by the presence of pottery such as the pieces that have been found in the Cueva del Escobar of Roturas and in Peñas María. They have also been found elsewhere in villages with a complex organisation such as the first tin mines (casiterite) at the Cerro de San Cristóbal of Logrosán. Their inhabitants were forerunners of those who left a record of their warlike nature in the form of stelae engraved in stone. A milestone in the research into this phenomenon is represented by the Stela of the Warrior of Solana de Cabañas del Castillo, which was the first of the discoveries of its kind. Here the representation of the personage is not only important in itself but also that of his attire: a shield with a V-shaped notch, a lance, a sword, a cart, a comb, a mirror, and an elbow brooch, the last two of which are indirect examples of contact with people who arrived from the eastern coasts, to whom we also owe the discovery in Berzocana of two gold necklaces and a bronze vase.
The presence of Iron Age settlers represented a continuation of the above, but with a different perspective, as the population of the area was now concentrated in the periphery of the sierras around small hill forts such as La Dehesilla and the Castrejón of Berzocana, those of the River Almonte in Retamosa and Aldeacentenera, the Castrejón of Alía, etc. They took refuge behind sturdy sloping walls which, however, were no obstacle for the Roman conquerors. The latter moved the inhabitants of the hill forts to small rural settlements on the peneplain. A good example of which are the numerous Roman ruins existing at La Colonia of Cañamero and on the pasturelands of Logrosán, Berzocana, and Aldeacentenera. The search for metals, essentially iron, led the settlers at times to explore the interior of the sierras, like the small centre between Roturas and Navezuelas and the mining village of Berzocana. The necropolis of the latter was excavated in the 1970s and has expanded the archaeological collection of this village.
The Visigoths were gradually added to the Roman substratum under conditions that cannot have been very different from those described above, only to disappear with the arrival of the Arabs, who undertook the large-scale colonisation in the sierras where they built hamlets and castles on top of the summits all along the outer mountain ranges. It is even likely that the presence of these citadels, where the layout of some of their streets and the ruins of their houses can still partially be seen. The population of the Sierras of Cabañas, Solana, and Berzocana was particularly dense, with villages at the Peñas María, La Cruz Rota, the Cancho del Reloj, El Terrero, El Castillejo, and the Cañamero Castle itself, which constitutes the continuity of settlements in the area during the Christian Reconquest.
The impetus of the Kingdom of Castile in the early 13th century and the consequent retreat of the Arabs towards the south brought another type of repopulation to the territory with cattle-raisers and beekeepers, who represented the genesis of most of the present villages. The semi-wild nature of the sierras also attracted kings and noblemen, according to the "Book of Hunting" of King Alfonso XI, which narrates the excellent bear and wild boar hunting that was to be had in this mountainous district. During these times, after the discovery of the statue of the Virgin, Guadalupe was founded as a Mudejar chapel and a hunting lodge. Soon after it attained the status of a Royal Monastery and from then on became the most important population centre in the region and through time a place of great historical importance. The Royal Monastery of Guadalupe was declared World Heritage by UNESCO in 1993.