A way descended from the ancient road that linked Toletum (Toledo) with Emerita Augusta (Mérida), together with another secondary but no less important road that ran from Caesarobriga (Talavera de la Reina) to Puerto de San Vicente. An existing infrastructure that would serve for the flow of pilgrims that began at the end of the 14th century and grew above all in the 15th and 16th centuries thanks to the religious, cultural and artistic significance acquired by the monastery of Guadalupe itself. Along it travelled kings, knights, soldiers, monks and clerics; troubadours, minstrels, burghers and beggars; the healthy and the sick, men and women, all of them, on foot or on horseback, alone or in groups that changed along the way as some left and others joined, all devotees of the Virgin, who to a greater or lesser extent gave shape and meaning to this route marked by its rugged terrain and the beauty of its valleys.
The Guadalupe way, historically the second way in Spain by number of pilgrims, has two routes that pass through Toledo. The reason lies in the origins of its episcopate, since Guadalupe has belonged, and still belongs, to the archdiocese of Toledo, and clerics, bishops and monks travelled there along this route.
Documents show that the Royal House of Habsburg held Guadalupe in great esteem (some of its members are buried in the shrine) and promoted it as a place of pilgrimage and a cultural and spiritual centre. Both Charles I and Philip II had a special fondness for the Hieronymite Order. The fruit of this Hieronymite relationship with the way can still be seen today in the crosses, fountains, churches and hospitals in its villages, paths and drove roads. The dangers of travelling the way are reflected in the epic history of the struggle between the Santa Hermandad and the first bandits; this mountainous area was a refuge for many bandits because of their constant hostility with the council of Toledo, which intensified in the 15th and 16th centuries. Many of the pilgrims travelling to Guadalupe were attacked by them, known at the time as golfines. With the Carlist wars in the 19th century and the Franco period in the 20th, banditry would resurface once again, this time driven by the political and social repression of the time.
From an artistic point of view, Toledo and Guadalupe show a parallel worth mentioning, not only in the Hieronymite architecture of the period but also in the illumination of choir books, embroidery and other artistic expressions.
