The Franciscans fled into Novo Mesto in 1469 from Bosnia, which had been destabilized by Ottoman raids. In 1472, they built the first section of the monastery, though it then took them several hundred years to complete it. The majority of the works took place in the wake of the ravaging fire of 1664 when the order renovated all the structures, built the church tower, added chapels to the navel, enlarged the monastery and built a boarding school.

The neo-gothic facade of the church dates back to 1866.

The monastery houses the city’s oldest library. Its beginnings reach back to the late 15th century and it stores some 12,000 books including numerous incunabula. Items worthy of note also include Metzinger’s altar images and his paintings in the monastery as well as a variety of renaissance tombstones. In front of the church stands the statue of the Franciscan composer Sattner.

The order led a gymnasium here between 1746 and 1870, which was then the city’s most important educational establishment attended by a number of noted Slovenians. The original gymnasium building stands on the northern side of the square.