Perched on the slopes of the Martani Mountains in the heart of Umbria, between the Puglia and Attone rivers, the ancient Gualdum Captaneorum castle was founded in 975, when Count Edoardo Cattaneo, a vassal of Emperor Otto II of Saxony, received it as a fief and built a fortress there. The name has Lombard origins: the toponym Gualdo, in fact, derives from Wald (forest, woodland) while Cattaneo from Captaneorum (captains, lords in the king’s service).

Due to its strategic and difficult-to-reach location, it was contested by nearby cities (Todi, Foligno, and Spoleto). In 1177, it passed into the hands of Frederick Barbarossa, to whom it was granted along with the municipalities of Montefalco and Bevagna. In 1198, it became a fiefdom of the Duchy of Spoleto, then the Counts of Antignano conquered it in 1216, and Pope Gregory IX purchased it in 1235. Then came the Trinci family of Foligno, who purchased it for 4,000 ducats from the mercenary captain Braccio Fortebracci. In 1439, it was annexed again to the Papal States, and in 1493, Pope Alexander VI Borgia ceded it to Foligno for administration, which decided to build a mighty fortress there. Occupied by Napoleon, like the rest of the Italian peninsula, it then returned to the Papal States until the unification of Italy (1860).

The true protagonist of the village is the Rocca—a fortress shaped like an equilateral triangle with three interconnecting towers and underground passages. Construction, designed by Francesco di Bartolomeo da Pietrasanta, began in 1494, according to the military standards of the time. The Rocca, named Dei Borgia in honor of Pope Alexander VI, was completed in 1500. Of particular interest is the central keep, which, at 20 meters high, dominates the entire village. Its stones reveal many interesting facts, such as the numerous figures who have visited it: from the first lord of the castle, Oliviero Giovanni di Foligno, to Pope Borgia, and even Galileo Galilei, who stayed there in 1624 and wrote: “It is a small compendium of the universe.”

From the fortress, we move to a small square overlooked by ancient houses and the Town Hall. Further away stands the parish church dedicated to Saints Anthony and Antoninus, dating back to the 13th century and renovated in the 19th century. Don’t miss the elegant Romanesque crypt, also known as the underground church, which houses the relics of the two saints and Blessed Ugolino.

Wandering through alleys and streets, among stone walls and hanging gardens, in a more isolated and panoramic location, we come across the Romanesque Church of Sant’Andrea with its massive bell tower. Further down, we come across the Church of Sant’Agostino, the oldest in the village. Founded in 1136 by the Benedictines, who dedicated a convent to it that no longer exists (suppressed by Pope Innocent X in 1652), the church experienced a turning point in 1258 with the settlement of the Augustinian hermits: it was this transition, under the guidance of the prior Blessed Ugolino da Gualdo Cattaneo, that marked its definitive identity with the new dedication to the Holy Bishop of Hippo. Inside you can admire a fresco of extraordinary power: the Crucifixion with Saints (1482) from the workshop of the Foligno painter Nicolò di Liberatore, known as Alunno. The work, charged with intense devotional pathos, shows Christ between the Virgin, Saint John, Saint Augustine and Blessed Ugolino, whose cell was in this very church. At the foot of the weeping crucifix is ​​the Magdalene. The church also houses a significant cycle of 17th-century paintings: two paintings by Andrea Polinori (Saint Catherine of Alexandria and Saint Augustine), a Madonna of the Rosary by Pier Paolo Sensini from Todi and a Purgatory by Francesco Providoni from Bologna.

The area surrounding Gualdo Cattaneo also offers the opportunity to discover numerous castles and fortified buildings, primarily built in the late Middle Ages (13th-14th centuries).

Among the fortifications, noteworthy are Barattano Castle, where you can admire the Church of San Bartolomeo (13th century) with 16th- and 17th-century frescoes and two 16th-century wooden angels; the fortified village of San Terenziano, built in the 14th century, where the church of the same name is worth a visit, a rare example of a construction consisting of two superimposed churches; Grutti Castle, to see the underground caves and the Romanesque Abbey of Santa Maria di Agello; Pozzo Castle, a remarkable architectural complex with unique medieval features; and Marcellano, built around the 12th century. The latter is famous for the living nativity scene held every year during the Christmas period: the entire village is involved in the representation with displays and scenes of traditional medieval life with dozens of costumed figures, artisan workshops demonstrating ancient manufacturing techniques, taverns serving mulled wine and local gastronomic delicacies.

Saragano Castle, once the residence of the Roman consul Lucius Lucinius Sura, is believed to be of Lombard origin. Ceralto Castle, on the other hand, can be considered a haven of peace, nestled in a natural setting of oak and Turkey oak trees. Near the castle grows one of the largest holm oaks in Umbria, estimated to be around 200 years old. The fortification system is completed by Simigni Castle, founded in 1103 and currently privately owned; Forte Sorgnano Castle; Pomonte Castle, surrounded by lush vegetation and featuring a quadrilateral layout punctuated by small towers; Torri Castle, with its entrance gate surmounted by the coat of arms of the Todi eagle; Cisterna Alta Castle, which stands on a hill above the Puglia River and dates back to the 13th century, and Speltara Castle, which, due to its location and air of mystery, was chosen by director Pupi Avati in 1993 for some scenes in the film Magnificat.

In honor of Blessed Ugolino, the town’s patron saint, the Arrampicata (Climbing Race) takes place in September. This is a historical reenactment of the attacks on Gualdo Cattaneo Castle from neighboring towns. On this occasion, the three districts (the Contrada del Monte, representing the common people; the Contrada della Pieve, symbolizing the clergy and religious authorities; and the Contrada della Rocca, symbolizing the administrators, priors, and ladies) compete in a race, carrying a scale model of the Rocca Borgia on their shoulders to the main square.

For those with a sweet tooth, try cicotto: the name derives from 16th-century cuisine, when it referred to the leg and therefore the leg of the animal. In Grutti (a hamlet of Gualdo Cattaneo), cicotto is a culinary tradition passed down from father to son. Unlike other areas of Umbria, where only the pork shank is used, all cuts of the animal are cooked: ears, trotters, shank, tongue, tripe, and other offal are processed and deboned by hand, washed, and diced. The meat is then placed in a vat and then in the oven under the porchetta, collecting the fat and the spices used to cook it: a blend of fresh rosemary, red garlic, black pepper, and fennel.

Cicotto is also used to make sauces, a typical local recipe with snails, and some recipes with chickpeas or beans.