The trials and tribulations of the way are forgotten in the joy of reaching this point, which is about four kilometres from the town of Guadalupe. For some fatigue turns into delight on contemplating the beauty and depth of the countryside and making out for the first time the silhouette of the Real Monasterio de Santa María de Guadalupe. For others it is the time to give thanks for the success of the enterprise, which is why the Chapel of El Humilladero was built in the 15th century. This small religious monument allowed the pilgrims arriving from the north on the Highroad to make a stop to pray before reaching the monastery. Even today five centuries later, this little treasure awaits and receives walkers who are art and heritage enthusiasts.

Several of the routes which reached Guadalupe from the north came together on the so-called Highroad, on which pilgrims from places such as Madrid, Segovia, El Escorial, and Toledo arrived at the sanctuary. When this road came to a point about four kilometres from the town of Guadalupe, the Alto de las Altamiras, travellers could contemplate for the first time the impressive appearance of the Real Monasterio. It was on this spot where it was decided to build in the early 15th century the Chapel of El Humilladero where pilgrims could pray and give thanks for having completed their journey without mishap.

In order to build the Chapel of El Humilladero of Guadalupe, which is also known as the Chapel of the Santa Cruz, the same pattern was used as for the Mudejar shrine of the cloister of the Real Monasterio de Guadalupe, with a square ground plan, template bricks, and Gothic decoration

As is the case with the shrine, a curious symbiosis arose between the Mudejar and Gothic styles; it is possible that its construction was the result of collaboration between Christian and Mudejar master builders. One of the best examples of this hybrid style is the Gothic ribbed vault constructed with template brick in the purest Mudejar style. On this vault a keystone represents the coat of arms of Castile surrounded by four angels.

The Humilladero has very fine proportions which are highlighted by the repetition of designs and decoration on each of its doorways which face the four points of the compass. These four doorways, with basket and pointed arches, gave access to the small interior and are currently closed with iron grilles. The decoration of some of the capitals and corbels is noteworthy in that they include motifs which are hard to interpret and may be inspired by medieval bestiaries. Some can be identified as angels, mythological beings, characters with musical instruments, quadrupeds, and a curious pagan figure defined as the ‘green man’ which is present in Romanesque and Gothic works all over Europe. Some of these sculptural elements are identical to others present on the entrance to the Monasterio de Guadalupe, which increases the links between both monuments.

Inside the chapel there is a granite cross which gave the chapel one of its names. The hipped roof is covered by Arab tiles and is the result of one of the restorations. In 1931 the Chapel of El Humilladero was declared a Historical Artistic Monument.