The village of Santa Maria del Monte was probably born in the Roman Age as a strategic point of sighting against the barbarian invasions; infact a lookout tower (the Tower of Arians) was erected on the high top of the mountain. In AD 389 the control of the fortalice passed to Sant’Ambrogio, the Bishop of Milan; here he built the first little church and celebrated a Holy Communion with other Bishops on an engraved altar.
The Sacro Monte became a place of worship; before the year 1000 a pre-romanesque church was consecrated in honour of Virgin Maria.
The strategic position of Santa Maria del Monte assumes a more great importance in Middle Ages, in particular in the period of the struggles between the papacy and the Empire. In 1045 the Lombardic nobility took possession of the fortalice. The army of Federico Barbarossa, the most dangerous opponent of the Ambrosian clergy, was put up here.
In 1400, with the rising to power of Visconti Family, Santa Maria went through a difficult period of deep decline: the fortalice was knocked down and woods began to grow wild and neglected.
Around the middle of the fifteenth century Caterina Moriggi from Pallanza and Giliana Puricelli from Verghera chose Santa Maria as hermitage place; they spent their lonely and ascetic life sheltered in some caverns and they died because of the plague. In 1474 the Pope Sisto IV decided to erect here an Augustian monastery.
The Via Sacra del Rosario (the Road of the Chapels) was carried out in 1604 by the inspiration and the support of the nun Tecla Maria Cid and of the friar Giovan Battista Aguggiari. Some of the most important artists and architects of that period worked at the project: between them we remember the Bernascone, the Nuvolone and the Legnanino.
Since 1800 Santa Maria del Monte became an important tourist destination, also thanks to the funicular railway, reopened in the 2000 after a long interruption.