The town of Guadalupe originated and grew up around the Real Monasterio, taking its name from the river where the image of the Virgin appeared. But Guadalupe, declared a Historical-Artistic Site in 1943, is more than the magnificence of the monastery. In this small town situated in the heart of the Geopark surrounded by exuberant landscape we find a place which has retained the charm of its popular architecture. Losing yourself in the alleyways of Guadalupe takes us back to a past in which Sephardic influences were mixed with those of a distinguished group of pilgrims from all sorts of places, and the stamp of royalty and the nobility from the Middle Ages to the present.

One of the attractions of this mountain town is its interesting historical centre, which has remained practically unaltered since the 14th to 16th centuries. Aspects to be emphasised are its colonnades, its balconies, and its small plazas.

The humility of the materials and the solidity of its most traditional architecture contrasts with the sumptuousness of the Real Monasterio. It is in this that much of its charm of Guadalupe lies. Where this dichotomy can most clearly be appreciated is in the Plaza de Santa María, the epicentre of the locality, which extends before the monastic enclosure. In its centre stands the fountain which according to tradition was the font of the first American Indian who had arrived in Europe brought by Columbus.

The streets off the plaza lead us to the old Jewish quarter, the personality of which is shown by its wooden colonnades, rows of old balconies full of flowers, and intricate narrow alleyways. The houses are of two storeys with a hallway and are built with beams of chestnut wood as this tree is abundant locally. The fountain known as the Fuente de los Tres Chorros dominates the plaza of the same name and it is here that some of the best preserved streets come together.

A noteworthy building of the town is the Colegio de Infantes or Colegio de Gramática, which was founded in the 16th century and catered for students of grammar, Latin, and humanities among other subjects. This exceptional building in the Mudejar style is today part of the Parador Nacional de Turismo state-run hotel.

Also of relevance is the old Hospital de San Juan Bautista (also known as the Men’s Hospital). It is a building with a Renaissance façade and a distinguished history. It was here that the first autopsy of the western world took place thanks to the permission of Pope Eugene IV. This event attracted notable scholars of medicine from all over Europe. For centuries it was one of the few places where surgery was performed. Many of the royal doctors did their training here.

Between the 14th and 16th centuries new hospitals were built to attend both pilgrims and other patients such as the Hospital Nuevo or Women’s Hospital, the Monks’ Infirmary, that of La Pasión, and that of San Sebastián.
Another building of interest is the Iglesia Nueva, a baroque church attributed to Manuel de Lara Churriguera. It has a baroque doorway and, three naves with a transept and a cupola and was built between 1730 and 1735 at the expense of the Duque de Veragua, a descendant of Columbus.

In the town there are five medieval arches which in former times gave access to the monastery. The most outstanding are that of Seville, which is the oldest, and that of San Pedro.

As a curiosity it can be mentioned that many famous personages have visited this town. Miguel de Cervantes, devoted to the Virgen de Guadalupe, travelled here to offer up the shackles with which he was held prisoner. Centuries later Doctor Fleming did his medical training here at the Men’s Hospital where he first came into contact with the fungus which would help him to change the world: Penicillum notatum.