The church and the convent of San Francesco, built after the following settlement of the Franciscan friars (1280), preserve valuable artistic evidence, an epigraphic and sculptural collection and a collection of religious art, with works from Monteleone and surroundings.

The main entrance of the Church of St. Francis in Monteleone di Spoleto opens on the square, to the right of the door called “the Clock”. This monument is perhaps the most striking and impressive work for its development, artistic and faith complexity. It is a book of stories, Saints and symbols to be discovered and read carefully. Its main building is today the Church of San Francesco, built in the fourteenth century on a former Benedictine chapel of the twelfth century. The original name is actually that of Santa Maria or Madonna dell’Assunta (Santa Maria di Monteleone is called in a code in 1393), but is commonly known with the name of the poor man of Assisi when, around 1280, the first Franciscans settled in the complex. In fact, until the suppression of the convent, the Franciscan order in Monteleone always used in every act the official seal bearing the emblem of the order surmounted by the image of the Virgin in heaven, with the following initial letters S (anctae) M (ariae).
The beginning of the construction dates back to the years 1282-1285 at the time of the pontificate of Pope Martin IV. The church, renewed in the fifteenth century, it was restored and resized radically after the earthquake on January 1703. The previous church was, in fact, bigger than the current one, as the rest appears in the outer wall, at the apse. The floor was raised between 1395 and 1398, with a round arch, reducing by one third the height of the original church, whose entrance was from the right side door, creating a new worship room at the bottom. The effects of this division are well visible in the interior floor of the church, which cuts the fresco of the Crucifixion on the left wall, further then mutilated by the subsequent opening of a modern door that leads in the upper part of the cloister. The main facade (facing North), damaged by various earthquakes and partially truncated at the top of the original crown, is adorned by a Roman-Gothic style portal. This portal is enriched by three twisted columns and reliefs with animals, human figures and angels, and is the work of Lombard masters. The last two bands that decorate the jambs, resting on two lions made in stone, are characterized by numerous figures reproducing flowers, fruits, animals, saints, angels, dragons, sun and moon. In the top bezel there is a fifteenth-century fresco, now fading, depicting the Madonna and the Child with Saints Francis and Nicola. On either side of the outer face, in specific lighting conditions, there are visible traces of devotional graffiti and a cross. On the right flank the mighty and carved buttresses give the building the character of a fortified place, accentuated by his location and his proximity to the door of the castle, along the walls. The interior has two aisles, divided by stone pillars. The largest is decorated with the beautiful wooden ceiling painted by Joseph Frigerio Nursia (1760); the lower is covered with vaults and ribs. The inner wall decoration presents many cycles of frescoes, often juxtaposed with each other (made between the fourteenth and sixteenth century), unfortunately partially damaged by numerous changes made. The following characters are portrayed: St. Giuliano, St. Mary Magdalen, St. George, St. Catherine of Alexandria, Mary Magdalene, Madonna with the Child, St Ilarione (?), a Dormitio Virginis, a Crucifixion, a High Priest Jesus. The memory of one of the altars of the most important families of Monteleone, then abandoned, is a quadrangular oil canvas depicting four saints facing the altar of the Blessed Sacrament, which in a scroll portrait at the foot of the frontal altar, with coat of arms of Rubeis family, recalls the restoration of the same under the care of the Rev. D. Giovanni Antonio De Rubeis. The fake letter reports the following memory: "SVB LEONE X° ERECTVM / SVB CLEM (ent) E RESTA(uratu)M / ET AVCTVMAERE. R. D. / IOAN (ni)S ANT(on)Y. DE RUBEIS." in other words " This altar erected under Leone X was restored under Clemente IX and enlarged by the Reverend Don Giovanni Antonio Rossi ". Twelve paintings depicting the Savior and the apostles adorn the right wall of the nave; a long marble inscription, located between St. Paul and St. Andrew, attests the gift made to the church in 1630 by Amico Sinibaldi, noble Roman knight (and a direct descendant of Sinibaldi family of Monteleone). Relevant importance have also the wooden crucifix of the XV century, located above the homonymous altar, and choir stalls. At the same aisle walls some altars of XVII-XVIII century are juxtaposed, with contemporary paintings, including a Madonna with the Child, St Francis of Paola and San Gaetano from Thiene and the Annunciation attributed to Augustine Masucci of 1723, coming from the Church of St. Nicholas. There is also a sixteenth-century organ, with case and choir decorated in the eighteenth century. Among the fonts, it is one that shows the Greek symbol of the Tau, last letter Hebrew alphabet, representing the fulfillment of the entire revealed word of God. The door that cuts the fresco of the Crucifixion, leads to the upper cloister, once covered by cross vaults (of which only evident traces remain). The nine lunettes (excluding the first), realized in the first half of XVIII century, are inherent in the life of St. Francis. At the foot of these, and all along the wall of the corridor, is grouped like an antiquarium a small collection of epigraphic and sculptural fragments of Roman, medieval and modern time, commissioned by the parish priest Don Angelo Corona. Part of the Medieval architectural material comes from the parish, while a headless woman statue was removed from the church of St. Erasmus in Trivio. Here it is also the Roman funerary inscription of Sesto Vettuleno, discovered decades ago in Forca di Usigni, in the municipality of Poggiodomo, and with the following text: "SEX VETTVLENVS. P. F. GRAGVS / VETTVLENA. SEX. F. VXOR ". The sacristy houses a small but impressive collection of religious art, which includes a Madonna with the Child from Castelvecchio, a wooden sculpture of the thirteenth century. From the upper cloister one can enter the lower one, rich in pictorial fragments dated between the fourteenth and fifteenth centuries. Here, beside an arched niche with a Madonna between the Saints, there is a rare fresco depicting the Universe subdivision according to the Ptolemaic system with the Earth at the center (which encloses itself the Infernus), it surrounded by items in hierarchy order according to the beliefs of the time. From an angular door one can enter the lower church choir, dedicated to Antonio of Padua. There are preserved vivid frescoes, mainly with Franciscan subject and dated between the end of the fourteenth and early fifteenth Century, which constitute an interesting example of the Southern Umbria painting. The central room, in correspondence to the upper nave, had various uses, such as the burial ground and then the theater. On the left there are some richly painted arcosolia. The church is occasionally open to the cult, is owned by the Fund for Religious Buildings (F.E.C.) of the Interior Ministry. The lower part of the cloister and convent buildings, the communal property, are often the place of art exhibitions, cultural events and meetings, as well as the seat of the Museum of the Biga.