For centuries members of royalty, the nobility, the clergy, and merchants and pilgrims travelled to the Real Monasterio de Santa María de Guadalupe from all points of Castile. Ever since in the early 14th century the image of the Virgin appeared and a chapel (now a monastery) was built in her honour, the site has been an important religious and cultural centre. As the pilgrimage became more relevant a whole network of ways and infrastructures arose to cater for the needs of the travellers. The Hospital del Obispo, San Román, La Avellaneda, and the Rincón de los Frailes are some of these medieval places which can still be enjoyed today.

Over time Guadalupe became more and more important as a religious epicentre until it was one of the main pilgrimage destinations in the whole of Europe. There is no doubt that the pilgrim who made the greatest contribution to the importance of the sanctuary was Isabel la Católica; she is recorded as having visited at least 16 times.

The mark of Guadalupe transcended that of a religious enclave and extended throughout the west of the Iberian Peninsula. To allow access to all those who intended to visit the monastery it was necessary to consolidate a network of roads under the auspices of the civil and religious authorities. Nowadays twelve roads or ways reach Guadalupe: the so-called Highroad from Madrid; that of the Montes de Toledo; that of La Jara from Calera y Chozas; that of Cabañeros; that of Levante; that of the Miners from Almadén; the Mozarabic Way from Monterrubio; the Roman Way from Mérida; the Visigothic Way from Alcuéscar; that of Monfragüe, that of The Discovers from Cáceres; and that of the Hieronymites from Yuste. These roads, true natural corridors which run through surprising and varied landscapes, constituted communication channels for culture and traditions, being in themselves an extraordinary historical heritage. This road network included elements inherent to the coming and going of pilgrims, such as bridges, inns, and hospitals.

On the Highroad we will find the Hospital del Obispo in the valley to which it gives its name. This building is situated in leafy woodland and was built in the 14th century to provide shelter for travellers in their passage through these unpopulated sierras. It appears to have been built on a hunting lodge of Peter I and was expanded on successive occasions. One of the extensions was on the initiative of the Bishop (Obispo) of Sigüenza, owing to which it took his name. It was during the 15th and 16th centuries when the Hospital acquired its greatest importance and gave accommodation to numerous pilgrims; its popularity fell at the end of the 18th century when it began to be abandoned. After the Civil War it became the headquarters of the Civil Guard to combat the maquis partisans. Now it has been partially restored and contains a small chapel.

Another of the interesting places along these age-old routes is San Román, a hamlet on the banks of the River Gualija which was abandoned as early as the 16th century. According to legend its inhabitants had to abandon their homes and establish themselves in Peraleda as a consequence of a plague of ants. Since then Peraleda has been known as Peraleda de San Román. Its Roman history is shown by the ashlars and columns used in the remains of the constructions which still manage to remain standing. One of these is the façade of the old church. Very near this abandoned hamlet and downstream of it stands an old bridge with a single arch which is known as the Roman Bridge.

Not far away in the vicinity of Fresnedoso de Ibor there is another abandoned hamlet, the history of which is extraordinarily similar. This is La Avellaneda, which in about the 15th century suffered a population exodus to the nearby Castañar de Ibor, in this case owing to a plague of termites. Despite this it continued to have a tiny population until a further plague of termites in the late 18th century. Nowadays on this solitary spot remains of several houses and the Church of El Cristo can still be seen. We can also see the so-called Fuente del Oro or Fuente Santa, the water of which was considered long ago to have medicinal properties.

Another most interesting place is the Rincón de los Frailes or Casa del Rincón de Valdepalacios, which is situated in Logrosán. It is a country estate with numerous outbuildings and constructions which was originally used to supply the Monasterio de Guadalupe with agricultural produce. It combined this activity with that of a hostelry, giving shelter to those who reached it from the south; in time it became a hamlet. It was sold off in the 19th century and still continues its agricultural activity, retaining its country house, Franciscan monastery, the old hostelry, the refectory, and the church. The latter still has part of the exceptional 16th-century tiling of Talavera which acted as an altarpiece.