In ancient times, this was known as the Mons Faliscorum area of the Falisco people (Etruscans), who came here following destruction of various towns in the ager faliscus by the Romans. However, it is also the "wine mountain" consecrated by the fame of "Est! Est!! Est!!!", whose vineyard blanket the hills sloping towards the Lake Bolsena basin.

The town (600 metres above sea level) is set in a strategic spot at the edge of the southern crater of the Volsini mountains. This area, crossed by the consular Via Cassia, is marked by its unmistakable silhouette, with the remains of the Rocca dei Papi fortress and the impressive cupola of Santa Margherita.

Its history is tied to the history of several popes, including Urban V, who is considered Montefiascone's main benefactor. He was responsible for the radical transformation of the fortress to host the pontifical court and the title of diocese. Honour is also due to Julius II, Leo X, Paul III and lastly, Pius IX, to whom the city residents dedicated the construction of a gate (Porta Pia) during his visit there in September 1857. Next to the Rocca, in the upper part of the city, is the cathedral of Santa Margherita, which has one of the largest domes in Italy. Construction began at the end of the fifteenth century and many artists worked on it, including a certain Magister Antiquus, Michele Sammicheli and Carlo Fontana (who designed the cupola in 1647). The facade, which has two bell towers, was completed in 1840 based on plans of Paolo Gazola. Inside, the crypt holds the remains of St. Margaret of Antioch, who was martyred under Diocletian. The interior of the church, which has an octagonal layout with seven chapels, holds various works of art, including a marble statue of St. Margaret (attributed to the school of Arnolfo di Cambio), a marvellous wooden crucifix, a Della Robbia-style terracotta work with the Madonna and Child, and a seventeenth-century altarpiece by the school of Sassoferrato depicting the Transit of St. Joseph.

Further downhill along the route of the ancient Via Francigena is the church of San Flaviano, one of the loveliest Romanesque structures in Viterbo's Tuscia area.

It was built in the eleventh century over pre-existing structures and it comprises two churches set one on top of the other. In the thirteenth century, it was redone extensively in the Gothic style during the papacy of Urban IV. The facade dates to this period, although the original Romanesque style of the upper portion and the bell gable were maintained. The entry portal, with a small Renaissance loggia over it that was covered up during the eighteenth century, leads to the lower church. The lower church has a nave and two aisles divided by pillars and columns with various types of capitals, some of which reflect a free interpretation of the Corinthian style. They sustain Gothic arches in the front section and Romanesque ones to the rear, which leads to the Romanesque women's gallery with a trussed roof. The small throne of Urban IV is located here. The three apses of the lower church, which are set in an arched shape, are quite intriguing.

Right nave: on the walls of the entrance, the Annunciation, the Nativity and the Adoration of the Magi. In the apse: Jesus and the Saints (fifteenth century). In the first arch is a large Giotto-like composition dating to the fourteenth century: in the upper part is the Crucifixion, while below there are scenes from the life of St. Nicholas of Bari, as well as St. Flavian between St. Margaret and St. Felicity and symbols of the virtues. In the upper part of the second arch is Our Lady enthroned surrounded by saints, while depicted in the lower part is a Crucifixion and the figures of St. John the Baptist and Urban IV (fifteenth century). In the apse: the Annunciation, dated 1575. On the vault of the middle apse, Christ the Teacher, while St. Flavian is depicted on the wall (sixteenth century). Left aisle: depicted in the apse is the Baptism of Jesus (sixteenth century). First arch: Madonna with Child and the Saints and the Deposition (sixteenth century). In the Gothic aedicule: the Eternal Father and the Visitation (sixteenth century); on the internal faces of the side pillars of the adjacent chapel, St. Sebastian (fifteenth century) and St. Barbara (sixteenth century). Inside the chapel are stones, slabs and sculptures from the ancient pagan temple, a thirteenth-century baptismal font and, on the ,left wall, the Madonna with Child (fifteenth century). In the next chapel, dedicated to Mary Magdalene, a noteworthy Crucifixion and St. Sebastian (fifteenth-sixteenth century) are depicted. On the entry arch to the Chapel of the Innocent is the Triumph of Death (fifteenth century), while inside is the Slaughter of the Innocent, a fresco dating to the fifteenth-sixteenth century and attributed to the school of Perugino. The chapel also has friezes, putti and other decorations attributed to Pastura. On the wall at the entrance to the church is a Crucifixion and scenes from the life of St. Catherine of Alexandria (fifteenth century). One of the surprising notes in this church is the gravestone of the abbot Defuk, who is linked with the legend of “Est! Est!! Est!!!” wine.

The other churches worth visiting are the church of Sant'Andrea, reconstructed in the eleventh century, and the country church of Santa Maria, designed in the first half of the sixteenth century by Sangallo the Younger. The historic centre is accessed through the eighteenth-century gate of Porta Aldrovandi. Here, we can see the Palazzo Comunale dominated by a massive bell tower, Palazzo Renzi, the well of Urban V and the house where Giovan Battista Casti, an abbot and man of letters, lived in around 1750.

The legend of Est!Est!!Est!!!

The year of Our Lord 1111. A men named Martin was travelling several days ahead of the imperial group heading to Rome (perhaps from the German city of Augusta) for the coronation of Henry V. The group included squires, prelates, noblemen, knights, pilgrims, lavies-in-waiting, merchants, dealers and a man named John Defuk a wine-lover and gourmand. Martin, his faithful factotum, was given the task of acting as a sommelier ahead of his times. In other words, he inspected the different wineries along the way to find good wine. Whenever he found it, he would write “Est” over the door, maining “it’s here”. When he found excellent wine, he would double the exclamation with “Est!Est!!”. When he reached Montefiascone, after tasting the local moscatello he immediately reinforced his affirmation with a triple “Est!Est!!Est!!!”. When Defuk arrived several days later, this recommendation did not escape him and, indeed, on his way back to Rome he decided to stay in Montefiascone forever, where it is said he died of too much wine. His remains were brought to the church of St. Flaviano, where a gravestone has immortalised his name.